# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 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 2057961'
loop_
_audit_author_name
_audit_author_address
'Ivan Potocnak'
;PJ Safarik University in Kosice
Slovakia
;
_audit_update_record             
;
2021-01-22 deposited with the CCDC.	2021-03-18 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         'C22 H12 Co N8'
_chemical_formula_sum            'C22 H12 Co N8'
_chemical_formula_weight         447.33

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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

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

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

_cell_length_a                   9.9045(2)
_cell_length_b                   15.9949(3)
_cell_length_c                   12.6185(2)
_cell_angle_alpha                90
_cell_angle_beta                 96.154(2)
_cell_angle_gamma                90
_cell_volume                     1987.52(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    15459
_cell_measurement_theta_min      4.1010
_cell_measurement_theta_max      29.2120

_exptl_crystal_description       prism
_exptl_crystal_colour            pink-red
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.495
_exptl_crystal_F_000             908
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.565
_exptl_crystal_size_mid          0.545
_exptl_crystal_size_min          0.320
_exptl_absorpt_coefficient_mu    0.891
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_correction_T_min  0.688
_exptl_absorpt_correction_T_max  0.827
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
Analytical numeric absorption correction using a multifaceted crystal
 model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_measurement_device_type  'Xcalibur, AtlasS2, Gemini ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 5.1783
_diffrn_reflns_number            28848
_diffrn_reflns_av_unetI/netI     0.0145
_diffrn_reflns_av_R_equivalents  0.0227
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         3.282
_diffrn_reflns_theta_max         26.497
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             4116
_reflns_number_gt                3772
_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 1.171.38.46 (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_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)+(0.0271P)²+1.1776P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4116
_refine_ls_number_parameters     280
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0269
_refine_ls_R_factor_gt           0.0233
_refine_ls_wR_factor_ref         0.0606
_refine_ls_wR_factor_gt          0.0582
_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         0.000

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
Co1 Co 0.22963(2) 0.52911(2) 0.77838(2) 0.01440(6) Uani 1 1 d . . . . .
N10 N 0.04716(11) 0.59050(7) 0.70957(9) 0.0145(2) Uani 1 1 d . . . . .
N20 N 0.22571(11) 0.50605(7) 0.60836(9) 0.0149(2) Uani 1 1 d . . . . .
N2 N 0.13056(13) 0.41567(7) 0.79850(10) 0.0214(3) Uani 1 1 d . . . . .
N1 N 0.05841(12) 0.28148(7) 0.71701(10) 0.0207(3) Uani 1 1 d . . . . .
N6 N 0.76672(13) 0.44025(8) 1.05809(10) 0.0218(3) Uani 1 1 d . . . . .
N3 N 0.17649(12) 0.14645(8) 0.74132(10) 0.0210(3) Uani 1 1 d . . . . .
N4 N 0.65693(12) 0.42969(8) 0.87423(10) 0.0242(3) Uani 1 1 d . . . . .
N5 N 0.42427(13) 0.47917(8) 0.82215(10) 0.0237(3) Uani 1 1 d . . . . .
C11 C 0.05464(13) 0.61187(8) 0.60842(11) 0.0154(3) Uani 1 1 d . . . . .
C2 C 0.10257(13) 0.35037(9) 0.76328(11) 0.0170(3) Uani 1 1 d . . . . .
C12 C -0.05178(13) 0.62582(8) 0.76337(11) 0.0158(3) Uani 1 1 d . . . . .
C3 C 0.12657(13) 0.21151(9) 0.73259(10) 0.0164(3) Uani 1 1 d . . . . .
C21 C 0.15456(13) 0.56425(8) 0.55140(11) 0.0152(3) Uani 1 1 d . . . . .
C22 C 0.30771(13) 0.45358(8) 0.55770(11) 0.0163(3) Uani 1 1 d . . . . .
C6 C 0.71151(14) 0.43662(9) 0.97313(11) 0.0180(3) Uani 1 1 d . . . . .
C23 C 0.36909(14) 0.38426(9) 0.61376(11) 0.0194(3) Uani 1 1 d . . . . .
H23 H 0.3533 0.3745 0.6857 0.023 Uiso 1 1 calc R U . . .
C27 C 0.32890(14) 0.46541(9) 0.44911(11) 0.0180(3) Uani 1 1 d . . . . .
C5 C 0.53263(15) 0.45729(9) 0.85141(11) 0.0190(3) Uani 1 1 d . . . . .
C29 C 0.16723(14) 0.57773(9) 0.44221(11) 0.0191(3) Uani 1 1 d . . . . .
H29 H 0.1143 0.6195 0.4036 0.023 Uiso 1 1 calc R U . . .
C13 C -0.07103(14) 0.59670(9) 0.86640(11) 0.0192(3) Uani 1 1 d . . . . .
H13 H -0.0147 0.5535 0.8983 0.023 Uiso 1 1 calc R U . . .
C17 C -0.13846(14) 0.68977(9) 0.71612(11) 0.0183(3) Uani 1 1 d . . . . .
C19 C -0.02999(14) 0.67356(9) 0.55609(11) 0.0191(3) Uani 1 1 d . . . . .
H19 H -0.0223 0.6872 0.4837 0.023 Uiso 1 1 calc R U . . .
C26 C 0.41886(15) 0.41115(9) 0.40191(12) 0.0221(3) Uani 1 1 d . . . . .
H26 H 0.4377 0.4204 0.3306 0.027 Uiso 1 1 calc R U . . .
C28 C 0.25642(15) 0.53009(9) 0.39261(11) 0.0202(3) Uani 1 1 d . . . . .
H28 H 0.2694 0.5406 0.3203 0.024 Uiso 1 1 calc R U . . .
C15 C -0.25502(15) 0.69512(10) 0.87414(12) 0.0239(3) Uani 1 1 d . . . . .
H15 H -0.3234 0.7183 0.9126 0.029 Uiso 1 1 calc R U . . .
C18 C -0.12301(14) 0.71335(9) 0.61065(11) 0.0202(3) Uani 1 1 d . . . . .
H18 H -0.1773 0.7569 0.5774 0.024 Uiso 1 1 calc R U . . .
C14 C -0.17089(15) 0.63069(9) 0.92038(12) 0.0222(3) Uani 1 1 d . . . . .
H14 H -0.1835 0.6107 0.9895 0.027 Uiso 1 1 calc R U . . .
C24 C 0.45107(15) 0.33145(9) 0.56438(12) 0.0232(3) Uani 1 1 d . . . . .
H24 H 0.4901 0.2844 0.6020 0.028 Uiso 1 1 calc R U . . .
C25 C 0.47848(15) 0.34574(10) 0.45876(12) 0.0243(3) Uani 1 1 d . . . . .
H25 H 0.5388 0.3097 0.4268 0.029 Uiso 1 1 calc R U . . .
C16 C -0.23912(15) 0.72432(9) 0.77485(12) 0.0225(3) Uani 1 1 d . . . . .
H16 H -0.2958 0.7681 0.7448 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
Co1 N2 2.0911(12) . ?
Co1 N5 2.1050(13) . ?
Co1 N6 2.1175(12) 3_667 ?
Co1 N3 2.1209(12) 2_556 ?
Co1 N10 2.1560(11) . ?
Co1 N20 2.1732(11) . ?
N10 C11 1.3310(17) . ?
N10 C12 1.3722(17) . ?
N20 C21 1.3309(17) . ?
N20 C22 1.3725(18) . ?
N2 C2 1.1571(19) . ?
N1 C2 1.3007(18) . ?
N1 C3 1.3109(18) . ?
N6 C6 1.1515(19) . ?
N6 Co1 2.1175(12) 3_667 ?
N3 C3 1.1523(19) . ?
N3 Co1 2.1209(12) 2_546 ?
N4 C6 1.3104(19) . ?
N4 C5 1.3105(19) . ?
N5 C5 1.1514(19) . ?
C11 C19 1.4119(19) . ?
C11 C21 1.4933(19) . ?
C12 C13 1.4131(19) . ?
C12 C17 1.4245(19) . ?
C21 C29 1.4134(19) . ?
C22 C23 1.417(2) . ?
C22 C27 1.4210(19) . ?
C23 C24 1.367(2) . ?
C23 H23 0.9500 . ?
C27 C28 1.409(2) . ?
C27 C26 1.420(2) . ?
C29 C28 1.368(2) . ?
C29 H29 0.9500 . ?
C13 C14 1.372(2) . ?
C13 H13 0.9500 . ?
C17 C18 1.407(2) . ?
C17 C16 1.417(2) . ?
C19 C18 1.365(2) . ?
C19 H19 0.9500 . ?
C26 C25 1.366(2) . ?
C26 H26 0.9500 . ?
C28 H28 0.9500 . ?
C15 C16 1.362(2) . ?
C15 C14 1.412(2) . ?
C15 H15 0.9500 . ?
C18 H18 0.9500 . ?
C14 H14 0.9500 . ?
C24 C25 1.407(2) . ?
C24 H24 0.9500 . ?
C25 H25 0.9500 . ?
C16 H16 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
N2 Co1 N5 93.86(5) . . ?
N2 Co1 N6 92.39(5) . 3_667 ?
N5 Co1 N6 84.99(5) . 3_667 ?
N2 Co1 N3 177.94(5) . 2_556 ?
N5 Co1 N3 88.04(5) . 2_556 ?
N6 Co1 N3 86.99(5) 3_667 2_556 ?
N2 Co1 N10 93.44(4) . . ?
N5 Co1 N10 169.44(5) . . ?
N6 Co1 N10 102.30(4) 3_667 . ?
N3 Co1 N10 84.77(4) 2_556 . ?
N2 Co1 N20 90.78(5) . . ?
N5 Co1 N20 96.52(5) . . ?
N6 Co1 N20 176.39(5) 3_667 . ?
N3 Co1 N20 89.78(5) 2_556 . ?
N10 Co1 N20 75.77(4) . . ?
C11 N10 C12 119.01(11) . . ?
C11 N10 Co1 111.88(9) . . ?
C12 N10 Co1 126.90(9) . . ?
C21 N20 C22 118.79(12) . . ?
C21 N20 Co1 111.52(9) . . ?
C22 N20 Co1 127.93(9) . . ?
C2 N2 Co1 146.39(11) . . ?
C2 N1 C3 120.85(12) . . ?
C6 N6 Co1 151.13(12) . 3_667 ?
C3 N3 Co1 167.67(12) . 2_546 ?
C6 N4 C5 117.56(12) . . ?
C5 N5 Co1 174.51(12) . . ?
N10 C11 C19 122.45(13) . . ?
N10 C11 C21 116.04(11) . . ?
C19 C11 C21 121.47(12) . . ?
N2 C2 N1 172.90(14) . . ?
N10 C12 C13 119.57(12) . . ?
N10 C12 C17 121.25(12) . . ?
C13 C12 C17 119.15(13) . . ?
N3 C3 N1 173.78(14) . . ?
N20 C21 C29 122.41(13) . . ?
N20 C21 C11 115.88(12) . . ?
C29 C21 C11 121.64(12) . . ?
N20 C22 C23 119.32(12) . . ?
N20 C22 C27 121.58(12) . . ?
C23 C22 C27 119.07(13) . . ?
N6 C6 N4 175.64(15) . . ?
C24 C23 C22 120.00(13) . . ?
C24 C23 H23 120.0 . . ?
C22 C23 H23 120.0 . . ?
C28 C27 C26 123.05(13) . . ?
C28 C27 C22 117.77(13) . . ?
C26 C27 C22 119.17(13) . . ?
N5 C5 N4 173.86(15) . . ?
C28 C29 C21 119.35(13) . . ?
C28 C29 H29 120.3 . . ?
C21 C29 H29 120.3 . . ?
C14 C13 C12 120.12(13) . . ?
C14 C13 H13 119.9 . . ?
C12 C13 H13 119.9 . . ?
C18 C17 C16 122.96(13) . . ?
C18 C17 C12 117.81(13) . . ?
C16 C17 C12 119.18(13) . . ?
C18 C19 C11 119.26(13) . . ?
C18 C19 H19 120.4 . . ?
C11 C19 H19 120.4 . . ?
C25 C26 C27 120.21(14) . . ?
C25 C26 H26 119.9 . . ?
C27 C26 H26 119.9 . . ?
C29 C28 C27 119.78(13) . . ?
C29 C28 H28 120.1 . . ?
C27 C28 H28 120.1 . . ?
C16 C15 C14 120.62(14) . . ?
C16 C15 H15 119.7 . . ?
C14 C15 H15 119.7 . . ?
C19 C18 C17 119.98(13) . . ?
C19 C18 H18 120.0 . . ?
C17 C18 H18 120.0 . . ?
C13 C14 C15 120.60(14) . . ?
C13 C14 H14 119.7 . . ?
C15 C14 H14 119.7 . . ?
C23 C24 C25 121.04(14) . . ?
C23 C24 H24 119.5 . . ?
C25 C24 H24 119.5 . . ?
C26 C25 C24 120.35(14) . . ?
C26 C25 H25 119.8 . . ?
C24 C25 H25 119.8 . . ?
C15 C16 C17 120.31(13) . . ?
C15 C16 H16 119.8 . . ?
C17 C16 H16 119.8 . . ?

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
C23 H23 N5 0.95 2.45 3.0347(19) 119.6 .
C13 H13 N6 0.95 2.46 3.1186(18) 126.3 3_667
C19 H19 N1 0.95 2.57 3.5019(19) 167.3 3_566

_refine_diff_density_max         0.316
_refine_diff_density_min         -0.293
_refine_diff_density_rms         0.045


_exptl_crystal_recrystallization_method 'from synthesis'
####################################################################### 
# 
# 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 2057962'
loop_
_audit_author_name
_audit_author_address
'Ivan Potocnak'
;PJ Safarik University in Kosice
Slovakia
;
_audit_update_record             
;
2021-01-22 deposited with the CCDC.	2021-03-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C22 H12 N8 Ni'
_chemical_formula_sum            'C22 H12 N8 Ni'
_chemical_formula_weight         447.11

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

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

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

_cell_length_a                   9.95420(10)
_cell_length_b                   15.89510(10)
_cell_length_c                   12.55570(10)
_cell_angle_alpha                90
_cell_angle_beta                 97.1780(10)
_cell_angle_gamma                90
_cell_volume                     1971.03(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    22687
_cell_measurement_theta_min      4.4880
_cell_measurement_theta_max      67.6460

_exptl_crystal_description       prism
_exptl_crystal_colour            blue
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.507
_exptl_crystal_F_000             912
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.258
_exptl_crystal_size_mid          0.157
_exptl_crystal_size_min          0.120
_exptl_absorpt_coefficient_mu    1.650
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_correction_T_min  0.751
_exptl_absorpt_correction_T_max  0.849
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.35c (Rigaku Oxford Diffraction, 2017)
Analytical numeric absorption correction using a multifaceted crystal
                        model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_measurement_device_type  'Xcalibur, AtlasS2, Gemini ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 5.1783
_diffrn_reflns_number            32308
_diffrn_reflns_av_unetI/netI     0.0109
_diffrn_reflns_av_R_equivalents  0.0238
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         4.510
_diffrn_reflns_theta_max         67.592
_diffrn_reflns_theta_full        67.592
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             3537
_reflns_number_gt                3399
_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 1.171.39.35c (Rigaku OD, 2017)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.35c (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.35c (Rigaku OD, 2017)'
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_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)+(0.0289P)²+1.2113P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3537
_refine_ls_number_parameters     280
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0245
_refine_ls_R_factor_gt           0.0236
_refine_ls_wR_factor_ref         0.0626
_refine_ls_wR_factor_gt          0.0620
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_restrained_S_all      1.052
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Ni1 Ni 0.23268(2) 0.53074(2) 0.77597(2) 0.01353(8) Uani 1 1 d . . . . .
N10 N 0.05221(11) 0.59112(7) 0.70989(9) 0.0142(2) Uani 1 1 d . . . . .
N20 N 0.22862(11) 0.50737(7) 0.60895(9) 0.0143(2) Uani 1 1 d . . . . .
N1 N 0.05407(12) 0.28175(7) 0.72239(10) 0.0200(3) Uani 1 1 d . . . . .
N3 N 0.17382(12) 0.14623(7) 0.74391(9) 0.0190(2) Uani 1 1 d . . . . .
N2 N 0.13688(12) 0.41809(7) 0.79582(9) 0.0193(2) Uani 1 1 d . . . . .
N5 N 0.42301(12) 0.48078(7) 0.82004(9) 0.0211(3) Uani 1 1 d . . . . .
N6 N 0.76307(12) 0.43794(7) 1.06275(9) 0.0197(3) Uani 1 1 d . . . . .
N4 N 0.65495(12) 0.43079(8) 0.87568(9) 0.0228(3) Uani 1 1 d . . . . .
C11 C 0.05802(13) 0.61322(8) 0.60823(10) 0.0149(3) Uani 1 1 d . . . . .
C2 C 0.10400(13) 0.35211(8) 0.76400(10) 0.0155(3) Uani 1 1 d . . . . .
C21 C 0.15693(13) 0.56604(8) 0.55141(10) 0.0149(3) Uani 1 1 d . . . . .
C12 C -0.04676(13) 0.62508(8) 0.76354(11) 0.0153(3) Uani 1 1 d . . . . .
C27 C 0.32910(14) 0.46626(8) 0.44946(11) 0.0170(3) Uani 1 1 d . . . . .
C22 C 0.30871(13) 0.45400(8) 0.55854(11) 0.0152(3) Uani 1 1 d . . . . .
C6 C 0.70857(13) 0.43597(8) 0.97632(11) 0.0166(3) Uani 1 1 d . . . . .
C3 C 0.12371(13) 0.21166(8) 0.73603(10) 0.0152(3) Uani 1 1 d . . . . .
C13 C -0.06485(14) 0.59454(9) 0.86668(11) 0.0182(3) Uani 1 1 d . . . . .
H13 H -0.007791 0.551195 0.898778 0.022 Uiso 1 1 calc R U . . .
C19 C -0.02845(14) 0.67486(9) 0.55548(11) 0.0186(3) Uani 1 1 d . . . . .
H19 H -0.021986 0.689161 0.482829 0.022 Uiso 1 1 calc R U . . .
C17 C -0.13503(13) 0.68889(8) 0.71600(11) 0.0174(3) Uani 1 1 d . . . . .
C23 C 0.36883(14) 0.38344(9) 0.61465(11) 0.0178(3) Uani 1 1 d . . . . .
H23 H 0.353503 0.373301 0.686721 0.021 Uiso 1 1 calc R U . . .
C5 C 0.53096(14) 0.45859(8) 0.85109(10) 0.0171(3) Uani 1 1 d . . . . .
C29 C 0.16883(14) 0.57984(9) 0.44164(11) 0.0182(3) Uani 1 1 d . . . . .
H29 H 0.116082 0.622065 0.402573 0.022 Uiso 1 1 calc R U . . .
C24 C 0.44887(14) 0.32995(9) 0.56513(11) 0.0216(3) Uani 1 1 d . . . . .
H24 H 0.486877 0.281954 0.602643 0.026 Uiso 1 1 calc R U . . .
C26 C 0.41716(14) 0.41134(9) 0.40218(11) 0.0208(3) Uani 1 1 d . . . . .
H26 H 0.435306 0.420801 0.330650 0.025 Uiso 1 1 calc R U . . .
C14 C -0.16454(14) 0.62740(9) 0.92033(11) 0.0211(3) Uani 1 1 d . . . . .
H14 H -0.176304 0.606432 0.989412 0.025 Uiso 1 1 calc R U . . .
C18 C -0.12131(14) 0.71361(9) 0.61005(11) 0.0199(3) Uani 1 1 d . . . . .
H18 H -0.176706 0.757230 0.576673 0.024 Uiso 1 1 calc R U . . .
C28 C 0.25687(14) 0.53190(9) 0.39232(11) 0.0193(3) Uani 1 1 d . . . . .
H28 H 0.269404 0.542731 0.319802 0.023 Uiso 1 1 calc R U . . .
C25 C 0.47585(15) 0.34499(9) 0.45915(12) 0.0231(3) Uani 1 1 d . . . . .
H25 H 0.535267 0.308681 0.427239 0.028 Uiso 1 1 calc R U . . .
C15 C -0.25002(15) 0.69213(9) 0.87404(12) 0.0233(3) Uani 1 1 d . . . . .
H15 H -0.318020 0.714726 0.912535 0.028 Uiso 1 1 calc R U . . .
C16 C -0.23553(14) 0.72242(9) 0.77431(12) 0.0213(3) Uani 1 1 d . . . . .
H16 H -0.293114 0.766157 0.743966 0.026 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Ni1 N2 2.0585(12) . ?
Ni1 N5 2.0650(12) . ?
Ni1 N6 2.0806(12) 3_667 ?
Ni1 N3 2.0871(12) 2_556 ?
Ni1 N10 2.1129(11) . ?
Ni1 N20 2.1251(11) . ?
N10 C11 1.3319(17) . ?
N10 C12 1.3717(17) . ?
N20 C21 1.3312(17) . ?
N20 C22 1.3718(17) . ?
N1 C2 1.3061(18) . ?
N1 C3 1.3120(18) . ?
N3 C3 1.1524(18) . ?
N2 C2 1.1549(18) . ?
N5 C5 1.1517(19) . ?
N6 C6 1.1514(18) . ?
N4 C5 1.3110(19) . ?
N4 C6 1.3114(18) . ?
C11 C19 1.4132(18) . ?
C11 C21 1.4887(18) . ?
C21 C29 1.4150(19) . ?
C12 C13 1.4154(19) . ?
C12 C17 1.4234(19) . ?
C27 C28 1.411(2) . ?
C27 C26 1.4187(19) . ?
C27 C22 1.4228(19) . ?
C22 C23 1.4167(19) . ?
C13 C14 1.371(2) . ?
C13 H13 0.9500 . ?
C19 C18 1.364(2) . ?
C19 H19 0.9500 . ?
C17 C18 1.410(2) . ?
C17 C16 1.416(2) . ?
C23 C24 1.367(2) . ?
C23 H23 0.9500 . ?
C29 C28 1.367(2) . ?
C29 H29 0.9500 . ?
C24 C25 1.410(2) . ?
C24 H24 0.9500 . ?
C26 C25 1.364(2) . ?
C26 H26 0.9500 . ?
C14 C15 1.413(2) . ?
C14 H14 0.9500 . ?
C18 H18 0.9500 . ?
C28 H28 0.9500 . ?
C25 H25 0.9500 . ?
C15 C16 1.366(2) . ?
C15 H15 0.9500 . ?
C16 H16 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
N2 Ni1 N5 93.24(5) . . ?
N2 Ni1 N6 92.51(5) . 3_667 ?
N5 Ni1 N6 85.69(5) . 3_667 ?
N2 Ni1 N3 178.85(5) . 2_556 ?
N5 Ni1 N3 87.84(5) . 2_556 ?
N6 Ni1 N3 87.18(5) 3_667 2_556 ?
N2 Ni1 N10 93.36(4) . . ?
N5 Ni1 N10 170.57(5) . . ?
N6 Ni1 N10 100.74(4) 3_667 . ?
N3 Ni1 N10 85.61(4) 2_556 . ?
N2 Ni1 N20 90.89(4) . . ?
N5 Ni1 N20 95.79(4) . . ?
N6 Ni1 N20 176.22(4) 3_667 . ?
N3 Ni1 N20 89.40(4) 2_556 . ?
N10 Ni1 N20 77.38(4) . . ?
C11 N10 C12 119.12(11) . . ?
C11 N10 Ni1 111.07(8) . . ?
C12 N10 Ni1 127.84(9) . . ?
C21 N20 C22 119.07(11) . . ?
C21 N20 Ni1 110.85(9) . . ?
C22 N20 Ni1 128.53(9) . . ?
C2 N1 C3 120.43(12) . . ?
C3 N3 Ni1 168.01(11) . 2_546 ?
C2 N2 Ni1 149.72(11) . . ?
C5 N5 Ni1 173.97(11) . . ?
C6 N6 Ni1 150.89(11) . 3_667 ?
C5 N4 C6 117.62(12) . . ?
N10 C11 C19 122.35(12) . . ?
N10 C11 C21 115.91(11) . . ?
C19 C11 C21 121.68(12) . . ?
N2 C2 N1 173.29(14) . . ?
N20 C21 C29 122.19(12) . . ?
N20 C21 C11 115.76(11) . . ?
C29 C21 C11 121.98(12) . . ?
N10 C12 C13 119.72(12) . . ?
N10 C12 C17 121.20(12) . . ?
C13 C12 C17 119.06(12) . . ?
C28 C27 C26 122.98(13) . . ?
C28 C27 C22 117.76(12) . . ?
C26 C27 C22 119.23(13) . . ?
N20 C22 C23 119.59(12) . . ?
N20 C22 C27 121.36(12) . . ?
C23 C22 C27 119.01(12) . . ?
N6 C6 N4 175.50(15) . . ?
N3 C3 N1 173.49(14) . . ?
C14 C13 C12 120.11(13) . . ?
C14 C13 H13 119.9 . . ?
C12 C13 H13 119.9 . . ?
C18 C19 C11 119.26(12) . . ?
C18 C19 H19 120.4 . . ?
C11 C19 H19 120.4 . . ?
C18 C17 C16 122.76(13) . . ?
C18 C17 C12 117.83(12) . . ?
C16 C17 C12 119.37(12) . . ?
C24 C23 C22 120.02(13) . . ?
C24 C23 H23 120.0 . . ?
C22 C23 H23 120.0 . . ?
N5 C5 N4 173.77(14) . . ?
C28 C29 C21 119.43(13) . . ?
C28 C29 H29 120.3 . . ?
C21 C29 H29 120.3 . . ?
C23 C24 C25 120.96(13) . . ?
C23 C24 H24 119.5 . . ?
C25 C24 H24 119.5 . . ?
C25 C26 C27 120.19(13) . . ?
C25 C26 H26 119.9 . . ?
C27 C26 H26 119.9 . . ?
C13 C14 C15 120.74(13) . . ?
C13 C14 H14 119.6 . . ?
C15 C14 H14 119.6 . . ?
C19 C18 C17 119.97(13) . . ?
C19 C18 H18 120.0 . . ?
C17 C18 H18 120.0 . . ?
C29 C28 C27 119.78(13) . . ?
C29 C28 H28 120.1 . . ?
C27 C28 H28 120.1 . . ?
C26 C25 C24 120.40(13) . . ?
C26 C25 H25 119.8 . . ?
C24 C25 H25 119.8 . . ?
C16 C15 C14 120.43(13) . . ?
C16 C15 H15 119.8 . . ?
C14 C15 H15 119.8 . . ?
C15 C16 C17 120.26(13) . . ?
C15 C16 H16 119.9 . . ?
C17 C16 H16 119.9 . . ?

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
_geom_hbond_publ_flag
C13 H13 N6 0.95 2.43 3.0676(18) 124.3 3_667 yes
C19 H19 N1 0.95 2.60 3.5342(18) 168.6 3_566 yes
C23 H23 N5 0.95 2.43 2.9978(18) 118.1 . yes

_refine_diff_density_max         0.240
_refine_diff_density_min         -0.407
_refine_diff_density_rms         0.046


_exptl_crystal_recrystallization_method 'from synthesis'
