# Electronic Supplementary Material (ESI) for Dalton Transactions.
# 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_py4cyclen
_database_code_depnum_ccdc_archive 'CCDC 1824553'
loop_
_audit_author_name
_audit_author_address
'Md. Ahsan Habib'
;Tohoku University
Japan
;
_audit_update_record             
;
2020-12-01 deposited with the CCDC.	2021-08-16 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C32 H40 N8'
_chemical_formula_weight         536.72

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'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

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

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.328(6)
_cell_length_b                   9.338(5)
_cell_length_c                   10.156(6)
_cell_angle_alpha                95.874(3)
_cell_angle_beta                 116.949(5)
_cell_angle_gamma                108.364(5)
_cell_volume                     716.3(7)
_cell_formula_units_Z            1
_cell_measurement_temperature    93
_cell_measurement_reflns_used    27.5087
_cell_measurement_theta_min      3.1664
_cell_measurement_theta_max      27.5087

_exptl_crystal_description       Plate
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.244
_exptl_crystal_F_000             288
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.900
_exptl_crystal_size_mid          0.800
_exptl_crystal_size_min          0.500
_exptl_absorpt_coefficient_mu    0.077
_shelx_estimated_absorpt_T_min   0.934
_shelx_estimated_absorpt_T_max   0.962
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.7756
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      93
_diffrn_radiation_wavelength     0.710747
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_source         'Rotating Anode'
_diffrn_radiation_monochromator  Confocal
_diffrn_radiation_detector       CCD
_diffrn_measurement_device       
;
Saturn724+ (4x4 bin mode)
;
_diffrn_detector_area_resol_mean 28.5714
_diffrn_measurement_method       dtprofit.ref
_diffrn_reflns_number            5764
_diffrn_reflns_av_unetI/netI     0.0480
_diffrn_reflns_av_R_equivalents  0.0290
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         4.058
_diffrn_reflns_theta_max         27.487
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.954
_diffrn_measured_fraction_theta_full 0.969
_diffrn_reflns_Laue_measured_fraction_max 0.954
_diffrn_reflns_Laue_measured_fraction_full 0.969
_diffrn_reflns_point_group_measured_fraction_max 0.954
_diffrn_reflns_point_group_measured_fraction_full 0.969
_reflns_number_total             3128
_reflns_number_gt                2438
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'Crystal Clear (Rigaku 2001)'
_computing_cell_refinement       'Crystal Clear (Rigaku 2001)'
_computing_data_reduction        'Crystal Clear (Rigaku 2001)'
_computing_structure_solution    'SHELXS-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_refine_special_details          ?

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0634P)²+0.0554P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3128
_refine_ls_number_parameters     181
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0617
_refine_ls_R_factor_gt           0.0454
_refine_ls_wR_factor_ref         0.1167
_refine_ls_wR_factor_gt          0.1083
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_restrained_S_all      1.046
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N3 N 0.25776(14) 0.34904(13) 0.72150(12) 0.0166(3) Uani 1 1 d . . . . .
N4 N 0.22904(16) 0.21050(15) 0.20766(13) 0.0233(3) Uani 1 1 d . . . . .
N2 N 0.42386(14) 0.67830(13) 0.98524(12) 0.0161(3) Uani 1 1 d . . . . .
N1 N 0.23291(16) 0.71800(15) 1.38167(14) 0.0247(3) Uani 1 1 d . . . . .
C8 C 0.22978(17) 0.49490(16) 0.71219(14) 0.0184(3) Uani 1 1 d . . . . .
H8A H 0.1328 0.4882 0.7309 0.022 Uiso 1 1 calc R U . . .
H8B H 0.1930 0.5042 0.6066 0.022 Uiso 1 1 calc R U . . .
C9 C 0.27011(17) 0.30159(16) 0.85862(14) 0.0170(3) Uani 1 1 d . . . . .
H9A H 0.1513 0.2329 0.8354 0.020 Uiso 1 1 calc R U . . .
H9B H 0.3180 0.3962 0.9444 0.020 Uiso 1 1 calc R U . . .
C7 C 0.39322(17) 0.64226(16) 0.82762(14) 0.0175(3) Uani 1 1 d . . . . .
H7A H 0.4974 0.6303 0.8330 0.021 Uiso 1 1 calc R U . . .
H7B H 0.3840 0.7335 0.7880 0.021 Uiso 1 1 calc R U . . .
C13 C 0.02389(17) 0.15600(16) 0.29698(15) 0.0185(3) Uani 1 1 d . . . . .
H13 H -0.0954 0.1133 0.2715 0.022 Uiso 1 1 calc R U . . .
C4 C 0.23156(17) 0.59500(17) 1.16056(15) 0.0193(3) Uani 1 1 d . . . . .
H4 H 0.2114 0.5009 1.0961 0.023 Uiso 1 1 calc R U . . .
C6 C 0.30547(18) 0.74750(16) 0.99185(15) 0.0192(3) Uani 1 1 d . . . . .
H6A H 0.1879 0.6918 0.8971 0.023 Uiso 1 1 calc R U . . .
H6B H 0.3511 0.8593 0.9938 0.023 Uiso 1 1 calc R U . . .
C16 C 0.35854(19) 0.27718(18) 0.35659(16) 0.0224(3) Uani 1 1 d . . . . .
H16 H 0.4766 0.3210 0.3789 0.027 Uiso 1 1 calc R U . . .
C14 C 0.15952(17) 0.22383(15) 0.45046(14) 0.0161(3) Uani 1 1 d . . . . .
C15 C 0.33052(18) 0.28594(17) 0.47941(15) 0.0200(3) Uani 1 1 d . . . . .
H15 H 0.4273 0.3340 0.5823 0.024 Uiso 1 1 calc R U . . .
C3 C 0.28607(17) 0.73879(16) 1.13087(15) 0.0182(3) Uani 1 1 d . . . . .
C11 C 0.12190(17) 0.22094(16) 0.58047(14) 0.0191(3) Uani 1 1 d . . . . .
H11A H 0.0074 0.2281 0.5462 0.023 Uiso 1 1 calc R U . . .
H11B H 0.1117 0.1189 0.6036 0.023 Uiso 1 1 calc R U . . .
C10 C 0.39019(17) 0.21293(16) 0.90713(15) 0.0186(3) Uani 1 1 d . . . . .
H10A H 0.3517 0.1362 0.9573 0.022 Uiso 1 1 calc R U . . .
H10B H 0.3794 0.1534 0.8142 0.022 Uiso 1 1 calc R U . . .
C2 C 0.31421(19) 0.87109(18) 1.23038(16) 0.0239(3) Uani 1 1 d . . . . .
H2 H 0.3526 0.9719 1.2156 0.029 Uiso 1 1 calc R U . . .
C1 C 0.2857(2) 0.85503(19) 1.35237(17) 0.0265(3) Uani 1 1 d . . . . .
H1 H 0.3050 0.9473 1.4188 0.032 Uiso 1 1 calc R U . . .
C12 C 0.06478(19) 0.15138(17) 0.18158(16) 0.0225(3) Uani 1 1 d . . . . .
H12 H -0.0296 0.1033 0.0777 0.027 Uiso 1 1 calc R U . . .
C5 C 0.20720(18) 0.59090(17) 1.28512(16) 0.0224(3) Uani 1 1 d . . . . .
H5 H 0.1699 0.4917 1.3033 0.027 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N3 C11 1.4619(18) . ?
N3 C8 1.4698(18) . ?
N3 C9 1.4704(17) . ?
N4 C12 1.339(2) . ?
N4 C16 1.3461(18) . ?
N2 C6 1.4662(18) . ?
N2 C7 1.4738(18) . ?
N2 C10 1.4762(18) 2_667 ?
N1 C1 1.335(2) . ?
N1 C5 1.3405(19) . ?
C8 C7 1.5232(19) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 C10 1.5331(18) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C13 C12 1.388(2) . ?
C13 C14 1.3917(18) . ?
C13 H13 0.9500 . ?
C4 C5 1.385(2) . ?
C4 C3 1.394(2) . ?
C4 H4 0.9500 . ?
C6 C3 1.510(2) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C16 C15 1.385(2) . ?
C16 H16 0.9500 . ?
C14 C15 1.387(2) . ?
C14 C11 1.5128(19) . ?
C15 H15 0.9500 . ?
C3 C2 1.384(2) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C10 N2 1.4763(18) 2_667 ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C2 C1 1.393(2) . ?
C2 H2 0.9500 . ?
C1 H1 0.9500 . ?
C12 H12 0.9500 . ?
C5 H5 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C11 N3 C8 110.52(10) . . ?
C11 N3 C9 110.82(11) . . ?
C8 N3 C9 114.03(10) . . ?
C12 N4 C16 115.90(12) . . ?
C6 N2 C7 110.38(9) . . ?
C6 N2 C10 110.86(12) . 2_667 ?
C7 N2 C10 108.99(11) . 2_667 ?
C1 N1 C5 116.04(13) . . ?
N3 C8 C7 113.10(11) . . ?
N3 C8 H8A 109.0 . . ?
C7 C8 H8A 109.0 . . ?
N3 C8 H8B 109.0 . . ?
C7 C8 H8B 109.0 . . ?
H8A C8 H8B 107.8 . . ?
N3 C9 C10 110.14(10) . . ?
N3 C9 H9A 109.6 . . ?
C10 C9 H9A 109.6 . . ?
N3 C9 H9B 109.6 . . ?
C10 C9 H9B 109.6 . . ?
H9A C9 H9B 108.1 . . ?
N2 C7 C8 115.49(11) . . ?
N2 C7 H7A 108.4 . . ?
C8 C7 H7A 108.4 . . ?
N2 C7 H7B 108.4 . . ?
C8 C7 H7B 108.4 . . ?
H7A C7 H7B 107.5 . . ?
C12 C13 C14 119.30(14) . . ?
C12 C13 H13 120.4 . . ?
C14 C13 H13 120.4 . . ?
C5 C4 C3 119.25(13) . . ?
C5 C4 H4 120.4 . . ?
C3 C4 H4 120.4 . . ?
N2 C6 C3 113.15(10) . . ?
N2 C6 H6A 108.9 . . ?
C3 C6 H6A 108.9 . . ?
N2 C6 H6B 108.9 . . ?
C3 C6 H6B 108.9 . . ?
H6A C6 H6B 107.8 . . ?
N4 C16 C15 124.12(14) . . ?
N4 C16 H16 117.9 . . ?
C15 C16 H16 117.9 . . ?
C15 C14 C13 117.36(12) . . ?
C15 C14 C11 121.44(12) . . ?
C13 C14 C11 121.10(13) . . ?
C16 C15 C14 119.27(12) . . ?
C16 C15 H15 120.4 . . ?
C14 C15 H15 120.4 . . ?
C2 C3 C4 117.16(13) . . ?
C2 C3 C6 121.79(13) . . ?
C4 C3 C6 120.99(12) . . ?
N3 C11 C14 113.13(12) . . ?
N3 C11 H11A 109.0 . . ?
C14 C11 H11A 109.0 . . ?
N3 C11 H11B 109.0 . . ?
C14 C11 H11B 109.0 . . ?
H11A C11 H11B 107.8 . . ?
N2 C10 C9 111.61(12) 2_667 . ?
N2 C10 H10A 109.3 2_667 . ?
C9 C10 H10A 109.3 . . ?
N2 C10 H10B 109.3 2_667 . ?
C9 C10 H10B 109.3 . . ?
H10A C10 H10B 108.0 . . ?
C3 C2 C1 119.39(14) . . ?
C3 C2 H2 120.3 . . ?
C1 C2 H2 120.3 . . ?
N1 C1 C2 124.02(14) . . ?
N1 C1 H1 118.0 . . ?
C2 C1 H1 118.0 . . ?
N4 C12 C13 124.05(13) . . ?
N4 C12 H12 118.0 . . ?
C13 C12 H12 118.0 . . ?
N1 C5 C4 124.14(14) . . ?
N1 C5 H5 117.9 . . ?
C4 C5 H5 117.9 . . ?

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
C11 N3 C8 C7 -161.47(10) . . . . ?
C9 N3 C8 C7 72.92(15) . . . . ?
C11 N3 C9 C10 84.75(14) . . . . ?
C8 N3 C9 C10 -149.79(11) . . . . ?
C6 N2 C7 C8 -76.88(15) . . . . ?
C10 N2 C7 C8 161.15(10) 2_667 . . . ?
N3 C8 C7 N2 -82.12(14) . . . . ?
C7 N2 C6 C3 161.29(11) . . . . ?
C10 N2 C6 C3 -77.85(14) 2_667 . . . ?
C12 N4 C16 C15 0.5(2) . . . . ?
C12 C13 C14 C15 0.91(19) . . . . ?
C12 C13 C14 C11 -175.53(12) . . . . ?
N4 C16 C15 C14 -0.4(2) . . . . ?
C13 C14 C15 C16 -0.35(19) . . . . ?
C11 C14 C15 C16 176.08(13) . . . . ?
C5 C4 C3 C2 0.48(18) . . . . ?
C5 C4 C3 C6 -176.92(12) . . . . ?
N2 C6 C3 C2 127.01(14) . . . . ?
N2 C6 C3 C4 -55.71(17) . . . . ?
C8 N3 C11 C14 81.86(13) . . . . ?
C9 N3 C11 C14 -150.74(11) . . . . ?
C15 C14 C11 N3 28.81(17) . . . . ?
C13 C14 C11 N3 -154.90(12) . . . . ?
N3 C9 C10 N2 88.64(13) . . . 2_667 ?
C4 C3 C2 C1 -0.7(2) . . . . ?
C6 C3 C2 C1 176.72(12) . . . . ?
C5 N1 C1 C2 0.0(2) . . . . ?
C3 C2 C1 N1 0.4(2) . . . . ?
C16 N4 C12 C13 0.1(2) . . . . ?
C14 C13 C12 N4 -0.8(2) . . . . ?
C1 N1 C5 C4 -0.2(2) . . . . ?
C3 C4 C5 N1 -0.1(2) . . . . ?

_refine_diff_density_max         0.358
_refine_diff_density_min         -0.178
_refine_diff_density_rms         0.044



####################################################################### 
# 
# 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 1837284'
loop_
_audit_author_name
_audit_author_address
'Md Ahsan Habib'
;Tohoku University
Japan
;
_audit_update_record             
;
2020-12-01 deposited with the CCDC.	2021-08-16 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C36 H44 Cl2 N4 Ni'
_chemical_formula_weight         662.36

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Ni Ni 0.3393 1.1124 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           ?
_space_group_name_H-M_alt        Ccm21
_space_group_name_Hall           ?

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

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

_cell_length_a                   7.7774(8)
_cell_length_b                   25.294(3)
_cell_length_c                   16.4763(17)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3241.3(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    3458
_cell_measurement_theta_min      2.472
_cell_measurement_theta_max      26.717

_exptl_crystal_description       plate
_exptl_crystal_colour            green
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.357
_exptl_crystal_F_000             1400
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.02
_exptl_absorpt_coefficient_mu    0.795
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker Apex II'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            8116
_diffrn_reflns_av_unetI/netI     0.0569
_diffrn_reflns_av_R_equivalents  0.0341
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -32
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.472
_diffrn_reflns_theta_max         26.717
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_point_group_measured_fraction_full 0.991
_reflns_number_total             3458
_reflns_number_gt                2809
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.907
_reflns_Friedel_fraction_max     0.973
_reflns_Friedel_fraction_full    0.983

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

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0833P)²+4.2720P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 1100 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.055(9)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         3458
_refine_ls_number_parameters     196
_refine_ls_number_restraints     15
_refine_ls_R_factor_all          0.0714
_refine_ls_R_factor_gt           0.0530
_refine_ls_wR_factor_ref         0.1428
_refine_ls_wR_factor_gt          0.1327
_refine_ls_goodness_of_fit_ref   0.998
_refine_ls_restrained_S_all      1.164
_refine_ls_shift/su_max          0.025
_refine_ls_shift/su_mean         0.001

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 0.3985(8) 0.1342(3) 0.2014(4) 0.0403(15) Uani 1 1 d . . . . .
C3 C 0.8650(9) 0.0877(3) -0.0057(4) 0.0393(15) Uani 1 1 d . . . . .
H3A H 0.7593 0.1080 -0.0043 0.047 Uiso 1 1 calc R U . . .
H3B H 0.8570 0.0630 -0.0506 0.047 Uiso 1 1 calc R U . . .
C4 C 0.4494(9) 0.0849(3) 0.1538(4) 0.0484(19) Uani 1 1 d . . . . .
H4A H 0.3528 0.0607 0.1542 0.058 Uiso 1 1 calc R U . . .
H4B H 0.4692 0.0952 0.0978 0.058 Uiso 1 1 calc R U . . .
C5 C 1.2962(12) 0.1405(4) -0.0754(6) 0.062(3) Uani 1 1 d . . . . .
H5 H 1.3901 0.1284 -0.1049 0.075 Uiso 1 1 calc R U . . .
C6 C 0.4056(13) 0.2286(4) 0.2144(7) 0.071(3) Uani 1 1 d . . . . .
H6 H 0.4439 0.2611 0.1954 0.085 Uiso 1 1 calc R U . . .
C7 C 1.1549(10) 0.1080(3) -0.0646(5) 0.0494(19) Uani 1 1 d . . . . .
H7 H 1.1543 0.0744 -0.0876 0.059 Uiso 1 1 calc R U . . .
C8 C 0.3014(10) 0.1321(4) 0.2698(7) 0.060(3) Uani 1 1 d . . . . .
H8 H 0.2639 0.0995 0.2891 0.072 Uiso 1 1 calc R U . . .
C9 C 1.2987(14) 0.1903(3) -0.0427(6) 0.062(2) Uani 1 1 d . . . . .
H9 H 1.3942 0.2120 -0.0496 0.075 Uiso 1 1 calc R U . . .
C10 C 1.0172(12) 0.1756(3) 0.0120(6) 0.059(2) Uani 1 1 d . . . . .
H10 H 0.9237 0.1880 0.0416 0.070 Uiso 1 1 calc R U . . .
C12 C 1.1596(13) 0.2077(3) 0.0001(7) 0.069(3) Uani 1 1 d . . . . .
H12 H 1.1601 0.2417 0.0216 0.083 Uiso 1 1 calc R U . . .
C13 C 0.4449(12) 0.1831(4) 0.1726(6) 0.063(2) Uani 1 1 d . . . . .
H13 H 0.5042 0.1855 0.1237 0.075 Uiso 1 1 calc R U . . .
C14 C 0.3113(15) 0.2258(4) 0.2830(7) 0.082(3) Uani 1 1 d . . . . .
H14 H 0.2825 0.2563 0.3114 0.098 Uiso 1 1 calc R U . . .
C15 C 0.2585(16) 0.1769(5) 0.3103(7) 0.091(4) Uani 1 1 d . . . . .
H15 H 0.1924 0.1746 0.3572 0.109 Uiso 1 1 calc R U . . .
C17 C 1.0150(9) 0.1249(3) -0.0204(4) 0.0393(15) Uani 1 1 d . . . . .
C020 C 0.7436(17) 0.0854(7) 0.2122(9) 0.0421(13) Uani 0.491(10) 1 d D . P A 2
H02A H 0.8180 0.0631 0.2448 0.051 Uiso 0.491(10) 1 calc R U P A 2
H02B H 0.7045 0.1147 0.2453 0.051 Uiso 0.491(10) 1 calc R U P A 2
C25B C 0.8372(17) 0.1051(6) 0.1388(8) 0.0421(13) Uani 0.491(10) 1 d D . P A 2
H25A H 0.9440 0.1215 0.1559 0.051 Uiso 0.491(10) 1 calc R U P A 2
H25B H 0.7680 0.1321 0.1126 0.051 Uiso 0.491(10) 1 calc R U P A 2
C20B C 0.7548(16) 0.0960(6) 0.1743(10) 0.0421(13) Uani 0.509(10) 1 d D . P A 1
H20A H 0.7201 0.1235 0.1368 0.051 Uiso 0.509(10) 1 calc R U P A 1
H20B H 0.7732 0.1126 0.2267 0.051 Uiso 0.509(10) 1 calc R U P A 1
C25A C 0.9243(16) 0.0738(7) 0.1457(7) 0.0421(13) Uani 0.509(10) 1 d D . P A 1
H25C H 1.0130 0.1007 0.1441 0.051 Uiso 0.509(10) 1 calc R U P A 1
H25D H 0.9622 0.0446 0.1796 0.051 Uiso 0.509(10) 1 calc R U P A 1
N1 N 0.8814(8) 0.0574(3) 0.0713(4) 0.066(2) Uani 1 1 d D . . . .
N2 N 0.6029(7) 0.0562(2) 0.1830(3) 0.0408(13) Uani 1 1 d D . . . .
Cl02 Cl 0.5079(3) 0.0000 -0.00676(15) 0.0452(6) Uani 1 2 d S T P . .
Cl03 Cl 1.0708(3) 0.0000 0.31314(12) 0.0399(5) Uani 1 2 d S T P . .
Ni01 Ni 0.69270(12) 0.0000 0.09866(6) 0.0316(3) Uani 1 2 d S T P A .
C10B C 1.0308(15) 0.0300(3) 0.0960(11) 0.0421(13) Uani 0.461(12) 1 d D . P A 2
H10A H 1.0582 0.0415 0.1506 0.051 Uiso 0.461(12) 1 calc R U P A 2
H10B H 1.1244 0.0415 0.0613 0.051 Uiso 0.461(12) 1 calc R U P A 2
C26A C 0.619(2) 0.0295(4) 0.2579(7) 0.0421(13) Uani 0.510(14) 1 d D . P A 1
H26A H 0.5263 0.0411 0.2927 0.051 Uiso 0.510(14) 1 calc R U P A 1
H26B H 0.7258 0.0411 0.2829 0.051 Uiso 0.510(14) 1 calc R U P A 1
C10A C 1.0400(14) 0.0199(4) 0.0442(7) 0.0421(13) Uani 0.539(12) 1 d D . P A 1
H10C H 1.0688 0.0304 -0.0108 0.051 Uiso 0.539(12) 1 calc R U P A 1
H10D H 1.1367 0.0304 0.0778 0.051 Uiso 0.539(12) 1 calc R U P A 1
C26B C 0.526(2) 0.0256(4) 0.2523(8) 0.0421(13) Uani 0.490(14) 1 d D . P A 2
H26C H 0.5844 0.0369 0.3013 0.051 Uiso 0.490(14) 1 calc R U P A 2
H26D H 0.4071 0.0369 0.2574 0.051 Uiso 0.490(14) 1 calc R U P 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
C1 C8 1.358(12) . ?
C1 C13 1.372(12) . ?
C1 C4 1.524(10) . ?
C3 N1 1.487(9) . ?
C3 C17 1.518(10) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C4 N2 1.478(9) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C5 C9 1.371(14) . ?
C5 C7 1.384(12) . ?
C5 H5 0.9300 . ?
C6 C14 1.350(16) . ?
C6 C13 1.375(13) . ?
C6 H6 0.9300 . ?
C7 C17 1.378(11) . ?
C7 H7 0.9300 . ?
C8 C15 1.359(16) . ?
C8 H8 0.9300 . ?
C9 C12 1.364(15) . ?
C9 H9 0.9300 . ?
C10 C12 1.387(13) . ?
C10 C17 1.390(11) . ?
C10 H10 0.9300 . ?
C12 H12 0.9300 . ?
C13 H13 0.9300 . ?
C14 C15 1.378(16) . ?
C14 H14 0.9300 . ?
C15 H15 0.9300 . ?
C020 N2 1.405(14) . ?
C020 C25B 1.498(17) . ?
C020 H02A 0.9700 . ?
C020 H02B 0.9700 . ?
C25B N1 1.677(14) . ?
C25B H25A 0.9700 . ?
C25B H25B 0.9700 . ?
C20B C25A 1.508(16) . ?
C20B N2 1.558(15) . ?
C20B H20A 0.9700 . ?
C20B H20B 0.9700 . ?
C25A N1 1.336(13) . ?
C25A H25C 0.9700 . ?
C25A H25D 0.9700 . ?
N1 C10B 1.412(12) . ?
N1 C10A 1.619(12) . ?
N1 Ni01 2.113(6) . ?
N2 C26A 1.413(12) . ?
N2 C26B 1.505(13) . ?
N2 Ni01 2.108(6) . ?
Cl02 Ni01 2.254(2) . ?
Ni01 N2 2.108(6) 4 ?
Ni01 N1 2.113(6) 4 ?
C10B C10B 1.519(13) 4 ?
C10B H10A 0.9700 . ?
C10B H10B 0.9700 . ?
C26A C26A 1.49(2) 4 ?
C26A H26A 0.9700 . ?
C26A H26B 0.9700 . ?
C10A C10A 1.007(18) 4 ?
C10A H10C 0.9700 . ?
C10A H10D 0.9700 . ?
C26B C26B 1.29(2) 4 ?
C26B H26C 0.9700 . ?
C26B H26D 0.9700 . ?

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
C8 C1 C13 118.0(8) . . ?
C8 C1 C4 122.6(7) . . ?
C13 C1 C4 119.4(7) . . ?
N1 C3 C17 112.9(6) . . ?
N1 C3 H3A 109.0 . . ?
C17 C3 H3A 109.0 . . ?
N1 C3 H3B 109.0 . . ?
C17 C3 H3B 109.0 . . ?
H3A C3 H3B 107.8 . . ?
N2 C4 C1 116.4(6) . . ?
N2 C4 H4A 108.2 . . ?
C1 C4 H4A 108.2 . . ?
N2 C4 H4B 108.2 . . ?
C1 C4 H4B 108.2 . . ?
H4A C4 H4B 107.3 . . ?
C9 C5 C7 120.5(9) . . ?
C9 C5 H5 119.7 . . ?
C7 C5 H5 119.7 . . ?
C14 C6 C13 119.7(9) . . ?
C14 C6 H6 120.1 . . ?
C13 C6 H6 120.1 . . ?
C17 C7 C5 120.7(8) . . ?
C17 C7 H7 119.7 . . ?
C5 C7 H7 119.7 . . ?
C1 C8 C15 120.8(10) . . ?
C1 C8 H8 119.6 . . ?
C15 C8 H8 119.6 . . ?
C12 C9 C5 119.2(9) . . ?
C12 C9 H9 120.4 . . ?
C5 C9 H9 120.4 . . ?
C12 C10 C17 119.8(8) . . ?
C12 C10 H10 120.1 . . ?
C17 C10 H10 120.1 . . ?
C9 C12 C10 121.2(8) . . ?
C9 C12 H12 119.4 . . ?
C10 C12 H12 119.4 . . ?
C1 C13 C6 121.5(8) . . ?
C1 C13 H13 119.2 . . ?
C6 C13 H13 119.2 . . ?
C6 C14 C15 118.9(9) . . ?
C6 C14 H14 120.6 . . ?
C15 C14 H14 120.6 . . ?
C14 C15 C8 121.0(10) . . ?
C14 C15 H15 119.5 . . ?
C8 C15 H15 119.5 . . ?
C7 C17 C10 118.6(7) . . ?
C7 C17 C3 119.9(7) . . ?
C10 C17 C3 121.4(7) . . ?
N2 C020 C25B 106.1(11) . . ?
N2 C020 H02A 110.5 . . ?
C25B C020 H02A 110.5 . . ?
N2 C020 H02B 110.5 . . ?
C25B C020 H02B 110.5 . . ?
H02A C020 H02B 108.7 . . ?
C020 C25B N1 113.3(11) . . ?
C020 C25B H25A 108.9 . . ?
N1 C25B H25A 108.9 . . ?
C020 C25B H25B 108.9 . . ?
N1 C25B H25B 108.9 . . ?
H25A C25B H25B 107.7 . . ?
C25A C20B N2 116.8(12) . . ?
C25A C20B H20A 108.1 . . ?
N2 C20B H20A 108.1 . . ?
C25A C20B H20B 108.1 . . ?
N2 C20B H20B 108.1 . . ?
H20A C20B H20B 107.3 . . ?
N1 C25A C20B 100.6(10) . . ?
N1 C25A H25C 111.6 . . ?
C20B C25A H25C 111.6 . . ?
N1 C25A H25D 111.6 . . ?
C20B C25A H25D 111.6 . . ?
H25C C25A H25D 109.4 . . ?
C25A N1 C3 130.2(10) . . ?
C10B N1 C3 124.7(9) . . ?
C25A N1 C10A 104.2(8) . . ?
C3 N1 C10A 97.6(6) . . ?
C10B N1 C25B 109.3(8) . . ?
C3 N1 C25B 100.2(7) . . ?
C25A N1 Ni01 101.0(7) . . ?
C10B N1 Ni01 100.0(6) . . ?
C3 N1 Ni01 118.4(4) . . ?
C10A N1 Ni01 100.7(5) . . ?
C25B N1 Ni01 102.2(6) . . ?
C26A N2 C4 126.4(8) . . ?
C020 N2 C4 118.9(9) . . ?
C020 N2 C26B 108.7(9) . . ?
C4 N2 C26B 100.3(7) . . ?
C26A N2 C20B 108.6(9) . . ?
C4 N2 C20B 105.4(8) . . ?
C26A N2 Ni01 102.8(6) . . ?
C020 N2 Ni01 108.8(7) . . ?
C4 N2 Ni01 112.6(4) . . ?
C26B N2 Ni01 106.5(5) . . ?
C20B N2 Ni01 97.1(6) . . ?
N2 Ni01 N2 84.9(3) . 4 ?
N2 Ni01 N1 146.6(2) . 4 ?
N2 Ni01 N1 84.7(3) 4 4 ?
N2 Ni01 N1 84.7(3) . . ?
N2 Ni01 N1 146.6(2) 4 . ?
N1 Ni01 N1 86.8(5) 4 . ?
N2 Ni01 Cl02 107.25(15) . . ?
N2 Ni01 Cl02 107.25(15) 4 . ?
N1 Ni01 Cl02 106.18(17) 4 . ?
N1 Ni01 Cl02 106.18(17) . . ?
N1 C10B C10B 119.4(4) . 4 ?
N1 C10B H10A 107.5 . . ?
C10B C10B H10A 107.5 4 . ?
N1 C10B H10B 107.5 . . ?
C10B C10B H10B 107.5 4 . ?
H10A C10B H10B 107.0 . . ?
N2 C26A C26A 118.6(5) . 4 ?
N2 C26A H26A 107.7 . . ?
C26A C26A H26A 107.7 4 . ?
N2 C26A H26B 107.7 . . ?
C26A C26A H26B 107.7 4 . ?
H26A C26A H26B 107.1 . . ?
C10A C10A N1 125.9(4) 4 . ?
C10A C10A H10C 105.9 4 . ?
N1 C10A H10C 105.8 . . ?
C10A C10A H10D 105.9 4 . ?
N1 C10A H10D 105.8 . . ?
H10C C10A H10D 106.2 . . ?
C26B C26B N2 121.0(5) 4 . ?
C26B C26B H26C 107.1 4 . ?
N2 C26B H26C 107.1 . . ?
C26B C26B H26D 107.1 4 . ?
N2 C26B H26D 107.1 . . ?
H26C C26B H26D 106.8 . . ?

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
C8 C1 C4 N2 -83.9(9) . . . . ?
C13 C1 C4 N2 99.2(9) . . . . ?
C9 C5 C7 C17 -0.6(14) . . . . ?
C13 C1 C8 C15 -3.0(14) . . . . ?
C4 C1 C8 C15 -179.8(9) . . . . ?
C7 C5 C9 C12 -0.5(15) . . . . ?
C5 C9 C12 C10 1.0(16) . . . . ?
C17 C10 C12 C9 -0.4(15) . . . . ?
C8 C1 C13 C6 4.6(13) . . . . ?
C4 C1 C13 C6 -178.4(8) . . . . ?
C14 C6 C13 C1 -3.7(15) . . . . ?
C13 C6 C14 C15 0.9(16) . . . . ?
C6 C14 C15 C8 0.7(19) . . . . ?
C1 C8 C15 C14 0.4(18) . . . . ?
C5 C7 C17 C10 1.2(12) . . . . ?
C5 C7 C17 C3 -176.9(7) . . . . ?
C12 C10 C17 C7 -0.7(12) . . . . ?
C12 C10 C17 C3 177.4(8) . . . . ?
N1 C3 C17 C7 92.2(9) . . . . ?
N1 C3 C17 C10 -85.9(9) . . . . ?
N2 C020 C25B N1 -51.0(14) . . . . ?
N2 C20B C25A N1 63.7(16) . . . . ?
C20B C25A N1 C3 80.9(13) . . . . ?
C20B C25A N1 C10A -166.1(10) . . . . ?
C20B C25A N1 Ni01 -62.0(12) . . . . ?
C17 C3 N1 C25A 46.1(12) . . . . ?
C17 C3 N1 C10B -48.4(11) . . . . ?
C17 C3 N1 C10A -69.7(7) . . . . ?
C17 C3 N1 C25B 73.9(8) . . . . ?
C17 C3 N1 Ni01 -176.2(5) . . . . ?
C020 C25B N1 C10B -81.6(12) . . . . ?
C020 C25B N1 C3 145.9(10) . . . . ?
C020 C25B N1 Ni01 23.7(11) . . . . ?
C25B C020 N2 C4 -78.5(12) . . . . ?
C25B C020 N2 C26B 167.8(10) . . . . ?
C25B C020 N2 Ni01 52.2(12) . . . . ?
C1 C4 N2 C26A 65.7(11) . . . . ?
C1 C4 N2 C020 -38.1(11) . . . . ?
C1 C4 N2 C26B 80.1(8) . . . . ?
C1 C4 N2 C20B -62.3(9) . . . . ?
C1 C4 N2 Ni01 -167.0(5) . . . . ?
C25A C20B N2 C26A 81.2(13) . . . . ?
C25A C20B N2 C4 -140.8(12) . . . . ?
C25A C20B N2 Ni01 -25.0(13) . . . . ?
C3 N1 C10B C10B -109.2(7) . . . 4 ?
C25B N1 C10B C10B 132.7(6) . . . 4 ?
Ni01 N1 C10B C10B 25.9(6) . . . 4 ?
C4 N2 C26A C26A 107.1(7) . . . 4 ?
C20B N2 C26A C26A -126.3(6) . . . 4 ?
Ni01 N2 C26A C26A -24.1(6) . . . 4 ?
C25A N1 C10A C10A 102.2(8) . . . 4 ?
C3 N1 C10A C10A -123.0(5) . . . 4 ?
Ni01 N1 C10A C10A -2.1(5) . . . 4 ?
C020 N2 C26B C26B -116.3(8) . . . 4 ?
C4 N2 C26B C26B 118.3(5) . . . 4 ?
Ni01 N2 C26B C26B 0.8(6) . . . 4 ?

_refine_diff_density_max         1.238
_refine_diff_density_min         -0.873
_refine_diff_density_rms         0.074



