# 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 2106446'
loop_
_audit_author_name
_audit_author_address
'Oscar Enrique Piro'
;Universidad Nacional de La Plata
Argentina
;
_audit_update_record             
;
2021-08-30 deposited with the CCDC.	2021-10-27 downloaded from the CCDC.
;
_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        diazido-tetrakis(1-methylimidazole)cobalt(II)
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C16 H24 Co N14'
_chemical_formula_weight         471.42

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'
Co Co 0.3494 0.9721 '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                   7.9088(7)
_cell_length_b                   8.9979(8)
_cell_length_c                   9.1722(8)
_cell_angle_alpha                83.382(7)
_cell_angle_beta                 77.031(7)
_cell_angle_gamma                73.001(7)
_cell_volume                     607.41(10)
_cell_formula_units_Z            1
_cell_measurement_temperature    297(2)
_cell_measurement_reflns_used    1263
_cell_measurement_theta_min      4.4880
_cell_measurement_theta_max      24.7440
_exptl_crystal_description       paralelepiped
_exptl_crystal_colour            violet
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.289
_exptl_crystal_F_000             245
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.390
_exptl_crystal_size_mid          0.332
_exptl_crystal_size_min          0.088
_exptl_absorpt_coefficient_mu    0.738
_shelx_estimated_absorpt_T_min   0.762
_shelx_estimated_absorpt_T_max   0.938
_exptl_absorpt_correction_T_min  0.90791
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_oxdiff_exptl_absorpt_empirical_full_min 0.880
_oxdiff_exptl_absorpt_empirical_full_max 1.249
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      297(2)
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            Eos
_diffrn_detector_area_resol_mean 16.0604
_diffrn_reflns_number            4539
_diffrn_reflns_av_unetI/netI     0.0601
_diffrn_reflns_av_R_equivalents  0.0318
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         3.097
_diffrn_reflns_theta_max         28.816
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.818
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.818
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.818
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             2600
_reflns_number_gt                2149
_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. 
Structure factors included contributions from the .fab file. 
_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       '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_solution    'SHELXT (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'ORTEP for Windows (Farrugia, 2012)'
_computing_publication_material  'SHELXL-2014/7 (Sheldrick, 2014)'
_refine_special_details          
;The crystal showed disordered solvent (water) which could not be modeled 
satisfactory. Therefore, it was resorted to the SQUEEZE (Van der Sluis and 
Spek, 1999) procedure to eliminate from the diffraction data the contribution 
due to this disordered electron density followed by the refinement of the 
ordered part.,SQUEEZE
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0441P)²+0.0138P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2600
_refine_ls_number_parameters     167
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0573
_refine_ls_R_factor_gt           0.0442
_refine_ls_wR_factor_ref         0.1051
_refine_ls_wR_factor_gt          0.0964
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_restrained_S_all      1.069
_refine_ls_shift/su_max          0.004
_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
C11 C 0.6312(3) 0.3800(3) 0.7788(3) 0.0320(6) Uani 1 1 d . . . . .
C12 C 0.6786(4) 0.6036(3) 0.7093(3) 0.0391(6) Uani 1 1 d . . . . .
C13 C 0.7423(4) 0.5553(4) 0.8358(3) 0.0428(7) Uani 1 1 d . . . . .
C14 C 0.7616(4) 0.3166(4) 1.0112(3) 0.0486(7) Uani 1 1 d . . . . .
H14A H 0.7284 0.2215 1.0153 0.073 Uiso 1 1 calc R U . . .
H14B H 0.6991 0.3716 1.0999 0.073 Uiso 1 1 calc R U . . .
H14C H 0.8895 0.2931 1.0048 0.073 Uiso 1 1 calc R U . . .
C21 C 0.3005(4) 0.8061(3) 0.6186(3) 0.0394(7) Uani 1 1 d . . . . .
C22 C 0.1153(3) 0.6829(4) 0.5947(4) 0.0455(7) Uani 1 1 d . . . . .
C23 C 0.0162(4) 0.8195(4) 0.6502(4) 0.0504(8) Uani 1 1 d . . . . .
C24 C 0.0885(5) 1.0522(4) 0.7261(5) 0.0736(11) Uani 1 1 d . . . . .
H24A H -0.0403 1.0932 0.7510 0.110 Uiso 0.5 1 calc R U P . .
H24B H 0.1375 1.0431 0.8145 0.110 Uiso 0.5 1 calc R U P . .
H24C H 0.1383 1.1211 0.6526 0.110 Uiso 0.5 1 calc R U P . .
H24D H 0.1973 1.0784 0.7277 0.110 Uiso 0.5 1 calc R U P . .
H24E H 0.0195 1.1285 0.6642 0.110 Uiso 0.5 1 calc R U P . .
H24F H 0.0187 1.0505 0.8262 0.110 Uiso 0.5 1 calc R U P . .
N1 N 0.6263(3) 0.6540(2) 0.4018(2) 0.0359(5) Uani 1 1 d . . . . .
N2 N 0.7242(3) 0.6381(2) 0.2806(3) 0.0354(5) Uani 1 1 d . . . . .
N3 N 0.8184(4) 0.6319(3) 0.1646(3) 0.0625(8) Uani 1 1 d . . . . .
N11 N 0.6070(2) 0.4927(2) 0.6736(2) 0.0298(5) Uani 1 1 d . . . . .
N12 N 0.7129(3) 0.4131(3) 0.8796(2) 0.0358(5) Uani 1 1 d . . . . .
N21 N 0.2951(2) 0.6736(2) 0.5749(2) 0.0299(5) Uani 1 1 d . . . . .
N22 N 0.1344(3) 0.8982(3) 0.6653(3) 0.0424(6) Uani 1 1 d . . . . .
Co Co 0.5000 0.5000 0.5000 0.02719(16) Uani 1 2 d S . P . .
H11 H 0.597(3) 0.288(3) 0.788(3) 0.028(6) Uiso 1 1 d . . . . .
H12 H 0.676(3) 0.700(3) 0.647(3) 0.041(7) Uiso 1 1 d . . . . .
H13 H 0.791(4) 0.603(4) 0.892(4) 0.058(9) Uiso 1 1 d . . . . .
H21 H 0.404(4) 0.834(3) 0.621(3) 0.045(8) Uiso 1 1 d . . . . .
H22 H 0.080(3) 0.589(4) 0.570(3) 0.049(8) Uiso 1 1 d . . . . .
H23 H -0.107(4) 0.875(4) 0.667(4) 0.062(9) 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
C11 N11 1.318(3) . ?
C11 N12 1.343(3) . ?
C12 C13 1.345(4) . ?
C12 N11 1.383(3) . ?
C13 N12 1.367(4) . ?
C14 N12 1.460(3) . ?
C21 N21 1.315(3) . ?
C21 N22 1.338(3) . ?
C22 C23 1.336(4) . ?
C22 N21 1.371(3) . ?
C23 N22 1.365(4) . ?
C24 N22 1.468(4) . ?
N1 N2 1.201(3) . ?
N1 Co 1.961(2) . ?
N2 N3 1.150(3) . ?
N11 Co 1.9504(19) . ?
N21 Co 1.9510(18) . ?
Co N11 1.9504(19) 2_666 ?
Co N21 1.9510(18) 2_666 ?
Co N1 1.961(2) 2_666 ?

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
N11 C11 N12 111.3(2) . . ?
C13 C12 N11 109.1(3) . . ?
C12 C13 N12 107.0(2) . . ?
N21 C21 N22 111.3(2) . . ?
C23 C22 N21 109.7(3) . . ?
C22 C23 N22 106.8(2) . . ?
N2 N1 Co 122.94(16) . . ?
N3 N2 N1 175.9(3) . . ?
C11 N11 C12 105.6(2) . . ?
C11 N11 Co 127.58(17) . . ?
C12 N11 Co 126.81(19) . . ?
C11 N12 C13 106.9(2) . . ?
C11 N12 C14 127.0(2) . . ?
C13 N12 C14 126.1(2) . . ?
C21 N21 C22 105.4(2) . . ?
C21 N21 Co 127.16(17) . . ?
C22 N21 Co 127.40(18) . . ?
C21 N22 C23 106.9(2) . . ?
C21 N22 C24 126.4(2) . . ?
C23 N22 C24 126.7(2) . . ?
N11 Co N11 180.0 . 2_666 ?
N11 Co N21 88.06(8) . 2_666 ?
N11 Co N21 91.94(8) 2_666 2_666 ?
N11 Co N21 91.94(8) . . ?
N11 Co N21 88.06(8) 2_666 . ?
N21 Co N21 180.0 2_666 . ?
N11 Co N1 88.64(9) . . ?
N11 Co N1 91.36(9) 2_666 . ?
N21 Co N1 92.33(8) 2_666 . ?
N21 Co N1 87.67(8) . . ?
N11 Co N1 91.36(9) . 2_666 ?
N11 Co N1 88.64(9) 2_666 2_666 ?
N21 Co N1 87.67(8) 2_666 2_666 ?
N21 Co N1 92.33(8) . 2_666 ?
N1 Co N1 180.0 . 2_666 ?

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
N11 C12 C13 N12 0.6(3) . . . . ?
N21 C22 C23 N22 0.3(4) . . . . ?
N12 C11 N11 C12 0.3(3) . . . . ?
N12 C11 N11 Co 178.57(14) . . . . ?
C13 C12 N11 C11 -0.6(3) . . . . ?
C13 C12 N11 Co -178.82(17) . . . . ?
N11 C11 N12 C13 0.0(3) . . . . ?
N11 C11 N12 C14 180.0(2) . . . . ?
C12 C13 N12 C11 -0.4(3) . . . . ?
C12 C13 N12 C14 179.6(2) . . . . ?
N22 C21 N21 C22 0.2(3) . . . . ?
N22 C21 N21 Co -179.17(18) . . . . ?
C23 C22 N21 C21 -0.3(4) . . . . ?
C23 C22 N21 Co 179.1(2) . . . . ?
N21 C21 N22 C23 -0.1(3) . . . . ?
N21 C21 N22 C24 178.0(3) . . . . ?
C22 C23 N22 C21 -0.1(4) . . . . ?
C22 C23 N22 C24 -178.2(3) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C14 H14C N3 0.96 2.70 3.489(4) 140.3 2_766
C13 H13 N3 0.91(3) 2.61(3) 3.386(4) 144(3) 1_556

_refine_diff_density_max         0.330
_refine_diff_density_min         -0.404
_refine_diff_density_rms         0.063




_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Methanol'
####################################################################### 
# 
# 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_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 2106447'
loop_
_audit_author_name
_audit_author_address
'Oscar Enrique Piro'
;Universidad Nacional de La Plata
Argentina
;
_audit_update_record             
;
2021-08-30 deposited with the CCDC.	2021-10-27 downloaded from the CCDC.
;
_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        diazido-tetrakis(1-methylimidazole)nickel(II)
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C16 H24 N14 Ni'
_chemical_formula_weight         471.20

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

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
_cell_length_a                   6.9174(5)
_cell_length_b                   9.0586(7)
_cell_length_c                   9.2754(8)
_cell_angle_alpha                76.786(7)
_cell_angle_beta                 75.450(7)
_cell_angle_gamma                80.212(6)
_cell_volume                     543.76(8)
_cell_formula_units_Z            1
_cell_measurement_temperature    297(2)
_cell_measurement_reflns_used    1323
_cell_measurement_theta_min      4.5560
_cell_measurement_theta_max      24.5630
_exptl_crystal_description       paralelepiped
_exptl_crystal_colour            blue
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.439
_exptl_crystal_F_000             246
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.393
_exptl_crystal_size_mid          0.293
_exptl_crystal_size_min          0.218
_exptl_absorpt_coefficient_mu    0.928
_shelx_estimated_absorpt_T_min   0.712
_shelx_estimated_absorpt_T_max   0.823
_exptl_absorpt_correction_T_min  0.95242
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_oxdiff_exptl_absorpt_empirical_full_min 0.909
_oxdiff_exptl_absorpt_empirical_full_max 1.132
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      297(2)
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            Eos
_diffrn_detector_area_resol_mean 16.0604
_diffrn_reflns_number            4064
_diffrn_reflns_av_unetI/netI     0.0570
_diffrn_reflns_av_R_equivalents  0.0283
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         3.064
_diffrn_reflns_theta_max         28.800
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.819
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.819
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.819
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             2337
_reflns_number_gt                2006
_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       '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_solution    'SHELXT (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'ORTEP for Windows (Farrugia, 2012)'
_computing_publication_material  'SHELXL-2014/7 (Sheldrick, 2014)'
_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)+(0.0232P)²+0.1006P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2337
_refine_ls_number_parameters     190
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0528
_refine_ls_R_factor_gt           0.0415
_refine_ls_wR_factor_ref         0.0829
_refine_ls_wR_factor_gt          0.0738
_refine_ls_goodness_of_fit_ref   1.102
_refine_ls_restrained_S_all      1.102
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C11 C 0.1829(4) 0.7653(3) 0.8863(3) 0.0303(6) Uani 1 1 d . . . . .
C12 C 0.4437(4) 0.8514(3) 0.9037(3) 0.0417(7) Uani 1 1 d . . . . .
C13 C 0.3255(4) 0.9723(3) 0.8461(3) 0.0478(8) Uani 1 1 d . . . . .
C14 C -0.0096(6) 1.0060(4) 0.7715(5) 0.0564(9) Uani 1 1 d . . . . .
C21 C 0.5935(4) 0.3620(3) 0.7134(3) 0.0335(6) Uani 1 1 d . . . . .
C22 C 0.2748(4) 0.4153(3) 0.7798(3) 0.0321(6) Uani 1 1 d . . . . .
C23 C 0.3106(4) 0.3543(3) 0.6540(3) 0.0349(6) Uani 1 1 d . . . . .
C24 C 0.6233(6) 0.2416(5) 0.4898(4) 0.0548(9) Uani 1 1 d . . . . .
N1 N 0.7838(3) 0.5673(3) 0.8725(2) 0.0379(5) Uani 1 1 d . . . . .
N2 N 0.8182(3) 0.6408(3) 0.7478(3) 0.0371(5) Uani 1 1 d . . . . .
N3 N 0.8573(4) 0.7147(4) 0.6266(3) 0.0687(8) Uani 1 1 d . . . . .
N11 N 0.3548(3) 0.7209(2) 0.9292(2) 0.0295(5) Uani 1 1 d . . . . .
N12 N 0.1592(3) 0.9173(2) 0.8340(2) 0.0356(5) Uani 1 1 d . . . . .
N21 N 0.4538(3) 0.4212(2) 0.8170(2) 0.0289(5) Uani 1 1 d . . . . .
N22 N 0.5149(3) 0.3193(2) 0.6134(2) 0.0328(5) Uani 1 1 d . . . . .
Ni Ni 0.5000 0.5000 1.0000 0.02713(15) Uani 1 2 d S . P . .
H12 H 0.570(4) 0.847(3) 0.932(3) 0.042(7) Uiso 1 1 d . . . . .
H13 H 0.341(4) 1.076(3) 0.822(3) 0.052(8) Uiso 1 1 d . . . . .
H14 H 0.088(3) 0.702(3) 0.889(2) 0.028(6) Uiso 1 1 d . . . . .
H14A H -0.087(6) 0.943(4) 0.749(4) 0.087(13) Uiso 1 1 d . . . . .
H14B H 0.037(6) 1.065(4) 0.674(4) 0.100(14) Uiso 1 1 d . . . . .
H14C H -0.081(5) 1.079(5) 0.832(4) 0.093(13) Uiso 1 1 d . . . . .
H21 H 0.730(4) 0.349(3) 0.707(2) 0.030(7) Uiso 1 1 d . . . . .
H22 H 0.145(4) 0.450(3) 0.839(3) 0.049(8) Uiso 1 1 d . . . . .
H23 H 0.223(4) 0.342(3) 0.594(3) 0.058(9) Uiso 1 1 d . . . . .
H24A H 0.572(5) 0.282(4) 0.405(4) 0.084(12) Uiso 1 1 d . . . . .
H24B H 0.630(6) 0.138(5) 0.520(4) 0.105(15) Uiso 1 1 d . . . . .
H24C H 0.770(6) 0.263(4) 0.467(4) 0.097(13) 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
C11 N11 1.317(3) . ?
C11 N12 1.348(3) . ?
C12 C13 1.342(4) . ?
C12 N11 1.371(3) . ?
C13 N12 1.367(4) . ?
C14 N12 1.467(4) . ?
C21 N21 1.318(3) . ?
C21 N22 1.339(3) . ?
C22 C23 1.353(4) . ?
C22 N21 1.378(3) . ?
C23 N22 1.369(3) . ?
C24 N22 1.460(4) . ?
N1 N2 1.184(3) . ?
N1 Ni 2.129(2) . ?
N2 N3 1.162(3) . ?
N11 Ni 2.1196(18) . ?
N21 Ni 2.0969(19) . ?
Ni N21 2.0970(19) 2_667 ?
Ni N11 2.1196(18) 2_667 ?
Ni N1 2.129(2) 2_667 ?

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
N11 C11 N12 111.2(2) . . ?
C13 C12 N11 110.0(3) . . ?
C12 C13 N12 106.5(2) . . ?
N21 C21 N22 112.1(2) . . ?
C23 C22 N21 110.0(2) . . ?
C22 C23 N22 106.0(2) . . ?
N2 N1 Ni 126.68(17) . . ?
N3 N2 N1 177.7(3) . . ?
C11 N11 C12 105.4(2) . . ?
C11 N11 Ni 131.24(17) . . ?
C12 N11 Ni 123.01(17) . . ?
C11 N12 C13 106.8(2) . . ?
C11 N12 C14 126.6(3) . . ?
C13 N12 C14 126.6(3) . . ?
C21 N21 C22 104.8(2) . . ?
C21 N21 Ni 126.58(17) . . ?
C22 N21 Ni 128.64(17) . . ?
C21 N22 C23 107.1(2) . . ?
C21 N22 C24 127.0(3) . . ?
C23 N22 C24 125.8(3) . . ?
N21 Ni N21 180.0 . 2_667 ?
N21 Ni N11 87.83(7) . 2_667 ?
N21 Ni N11 92.17(7) 2_667 2_667 ?
N21 Ni N11 92.17(7) . . ?
N21 Ni N11 87.83(7) 2_667 . ?
N11 Ni N11 180.00(10) 2_667 . ?
N21 Ni N1 88.55(8) . 2_667 ?
N21 Ni N1 91.45(8) 2_667 2_667 ?
N11 Ni N1 90.89(8) 2_667 2_667 ?
N11 Ni N1 89.11(8) . 2_667 ?
N21 Ni N1 91.45(8) . . ?
N21 Ni N1 88.55(8) 2_667 . ?
N11 Ni N1 89.11(8) 2_667 . ?
N11 Ni N1 90.89(8) . . ?
N1 Ni N1 180.0 2_667 . ?

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
N11 C12 C13 N12 -0.4(3) . . . . ?
N21 C22 C23 N22 0.9(3) . . . . ?
N12 C11 N11 C12 0.4(3) . . . . ?
N12 C11 N11 Ni -172.96(15) . . . . ?
C13 C12 N11 C11 0.0(3) . . . . ?
C13 C12 N11 Ni 174.02(19) . . . . ?
N11 C11 N12 C13 -0.6(3) . . . . ?
N11 C11 N12 C14 177.6(3) . . . . ?
C12 C13 N12 C11 0.6(3) . . . . ?
C12 C13 N12 C14 -177.6(3) . . . . ?
N22 C21 N21 C22 0.0(3) . . . . ?
N22 C21 N21 Ni 178.53(14) . . . . ?
C23 C22 N21 C21 -0.6(3) . . . . ?
C23 C22 N21 Ni -179.05(16) . . . . ?
N21 C21 N22 C23 0.5(3) . . . . ?
N21 C21 N22 C24 -176.0(3) . . . . ?
C22 C23 N22 C21 -0.9(3) . . . . ?
C22 C23 N22 C24 175.7(3) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C11 H14 N1 0.93(2) 2.66(2) 3.580(3) 169.7(18) 1_455
C14 H14A N3 0.93(4) 2.70(4) 3.562(5) 154(3) 1_455
C22 H22 N1 0.97(3) 2.52(3) 3.414(3) 154(2) 1_455
C23 H23 N3 0.95(3) 2.43(3) 3.320(4) 155(2) 2_666
C24 H24C N3 1.02(4) 2.54(4) 3.546(5) 169(3) 2_766

_refine_diff_density_max         0.276
_refine_diff_density_min         -0.260
_refine_diff_density_rms         0.062



_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Methanol'
