# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2020

####################################################################### 
# 
# 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_I
_database_code_depnum_ccdc_archive 'CCDC 2020183'
loop_
_audit_author_name
_audit_author_address
'Norihito Fukui'
;Nagoya University
Japan
;
_audit_update_record             
;
2020-07-30 deposited with the CCDC.	2020-09-25 downloaded from the CCDC.
;
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C10 H7 N2 Ni0.50'
_chemical_formula_iupac          ?
_chemical_formula_weight         184.53

_chemical_melting_point          ?

_space_group_crystal_system      monoclinic
_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                   19.3223(7)
_cell_length_b                   4.66930(10)
_cell_length_c                   17.6807(6)
_cell_angle_alpha                90
_cell_angle_beta                 112.336(4)
_cell_angle_gamma                90
_cell_volume                     1475.50(9)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    3852
_cell_measurement_theta_min      1.9770
_cell_measurement_theta_max      30.9690
_cell_measurement_temperature    93.(2)

_exptl_crystal_description       plate
_exptl_crystal_colour            black
_exptl_crystal_size_max          0.456
_exptl_crystal_size_mid          0.083
_exptl_crystal_size_min          0.018
_exptl_crystal_density_diffrn    1.661
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             760

_exptl_absorpt_coefficient_mu    1.325
_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.
;
_exptl_absorpt_correction_T_min  0.56892
_exptl_absorpt_correction_T_max  1.00000

_exptl_special_details           
;
;

_diffrn_ambient_temperature      93.(2)

_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'

_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  graphite

_diffrn_measurement_device_type  
'dtrek-CrysAlisPro-abstract goniometer imported rigaku-d*trek images'
_diffrn_measurement_method       'ω scans'

_diffrn_detector_area_resol_mean ?

_diffrn_reflns_number            5961
_diffrn_reflns_av_R_equivalents  0.0190
_diffrn_reflns_av_unetI/netI     0.0154
_diffrn_reflns_theta_min         3.97
_diffrn_reflns_theta_max         28.99
_diffrn_reflns_theta_full        28.99
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 0.993
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       24

_refine_special_details          
;
;

_reflns_number_total             1952
_reflns_number_gt                1752
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0486
_refine_ls_R_factor_gt           0.0450
_refine_ls_wR_factor_gt          0.1222
_refine_ls_wR_factor_ref         0.1253
_refine_ls_goodness_of_fit_ref   1.076
_refine_ls_restrained_S_all      1.076
_refine_ls_number_reflns         1952
_refine_ls_number_parameters     116
_refine_ls_number_restraints     0
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0749P)²+2.9837P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         1.323
_refine_diff_density_min         -0.381
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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'

_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 2014/4 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C C1 0.35252(13) -0.0530(5) 0.46394(15) 0.0266(4) Uani d . . . 1 . .
N N1 0.40369(10) 0.0878(5) 0.44321(12) 0.0257(4) Uani d . . . 1 . .
Ni Ni1 0.5 0 0.5 0.02444(16) Uani d . P S 1 . .
C C2 0.28133(13) 0.0529(6) 0.41307(16) 0.0319(5) Uani d . . . 1 . .
H H1 0.2344 -0.0067 0.4134 0.038 Uiso calc U . R 1 . .
C C3 0.29276(12) 0.2604(6) 0.36261(14) 0.0317(5) Uani d . . . 1 . .
H H2 0.255 0.3687 0.3222 0.038 Uiso calc U . R 1 . .
C C4 0.37165(12) 0.2817(5) 0.38242(13) 0.0279(4) Uani d . . . 1 . .
N N2 0.53567(10) 0.2456(4) 0.44597(12) 0.0270(4) Uani d . . . 1 . .
C C5 0.41755(17) 0.4519(6) 0.35167(16) 0.0338(5) Uani d . . . 1 . .
C C6 0.49890(15) 0.4311(6) 0.38356(15) 0.0312(5) Uani d . . . 1 . .
C C7 0.55680(16) 0.5705(6) 0.36467(17) 0.0369(6) Uani d . . . 1 . .
H H3 0.5495 0.7103 0.3233 0.044 Uiso calc U . R 1 . .
C C8 0.62482(17) 0.4653(6) 0.41727(18) 0.0361(6) Uani d . . . 1 . .
H H4 0.6727 0.5214 0.4191 0.043 Uiso calc U . R 1 . .
C C10 0.38044(15) 0.6526(6) 0.28253(15) 0.0383(6) Uani d . . . 1 . .
H H5 0.3531 0.5428 0.2329 0.057 Uiso calc U . R 1 . .
H H6 0.4184 0.7717 0.2735 0.057 Uiso calc U . R 1 . .
H H7 0.3454 0.7754 0.2957 0.057 Uiso calc U . R 1 . .
C C9 0.61023(12) 0.2563(5) 0.46868(14) 0.0275(4) Uani d . . . 1 . .


_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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
C1 N1 . 1.349(3) ?
C1 C2 . 1.416(3) ?
C1 C9 5_656 1.479(3) ?
N1 C4 . 1.361(3) ?
N1 Ni1 . 1.7941(18) ?
Ni1 N2 5_656 1.7899(19) ?
Ni1 N2 . 1.7899(19) ?
Ni1 N1 5_656 1.7941(18) ?
C2 C3 . 1.390(4) ?
C2 H1 . 0.95 ?
C3 C4 . 1.432(3) ?
C3 H2 . 0.95 ?
C4 C5 . 1.442(4) ?
N2 C9 . 1.341(3) ?
N2 C6 . 1.370(3) ?
C5 C6 . 1.458(4) ?
C5 C10 . 1.490(4) ?
C6 C7 . 1.439(4) ?
C7 C8 . 1.380(4) ?
C7 H3 . 0.95 ?
C8 C9 . 1.433(3) ?
C8 H4 . 0.95 ?
C10 H5 . 0.98 ?
C10 H6 . 0.98 ?
C10 H7 . 0.98 ?
C9 C1 5_656 1.479(3) ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
N1 C1 C2 . . 107.0(2) ?
N1 C1 C9 . 5_656 110.42(19) ?
C2 C1 C9 . 5_656 142.5(2) ?
C1 N1 C4 . . 112.22(19) ?
C1 N1 Ni1 . . 116.62(16) ?
C4 N1 Ni1 . . 131.13(16) ?
N2 Ni1 N2 5_656 . 180.00(10) ?
N2 Ni1 N1 5_656 5_656 94.75(8) ?
N2 Ni1 N1 . 5_656 85.25(8) ?
N2 Ni1 N1 5_656 . 85.25(9) ?
N2 Ni1 N1 . . 94.75(8) ?
N1 Ni1 N1 5_656 . 180.0 ?
C3 C2 C1 . . 107.3(2) ?
C3 C2 H1 . . 126.3 ?
C1 C2 H1 . . 126.3 ?
C2 C3 C4 . . 107.8(2) ?
C2 C3 H2 . . 126.1 ?
C4 C3 H2 . . 126.1 ?
N1 C4 C3 . . 105.6(2) ?
N1 C4 C5 . . 120.3(2) ?
C3 C4 C5 . . 134.1(2) ?
C9 N2 C6 . . 112.8(2) ?
C9 N2 Ni1 . . 116.84(16) ?
C6 N2 Ni1 . . 130.39(17) ?
C4 C5 C6 . . 123.0(2) ?
C4 C5 C10 . . 118.9(2) ?
C6 C5 C10 . . 118.1(2) ?
N2 C6 C7 . . 105.2(2) ?
N2 C6 C5 . . 120.5(2) ?
C7 C6 C5 . . 134.4(2) ?
C8 C7 C6 . . 107.9(2) ?
C8 C7 H3 . . 126.0 ?
C6 C7 H3 . . 126.0 ?
C7 C8 C9 . . 107.7(2) ?
C7 C8 H4 . . 126.2 ?
C9 C8 H4 . . 126.2 ?
C5 C10 H5 . . 109.5 ?
C5 C10 H6 . . 109.5 ?
H5 C10 H6 . . 109.5 ?
C5 C10 H7 . . 109.5 ?
H5 C10 H7 . . 109.5 ?
H6 C10 H7 . . 109.5 ?
N2 C9 C8 . . 106.4(2) ?
N2 C9 C1 . 5_656 110.86(19) ?
C8 C9 C1 . 5_656 142.7(2) ?

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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C2 C1 N1 C4 . . . . 0.4(3) ?
C9 C1 N1 C4 5_656 . . . -178.71(19) ?
C2 C1 N1 Ni1 . . . . 178.83(16) ?
C9 C1 N1 Ni1 5_656 . . . -0.3(3) ?
C1 N1 Ni1 N2 . . . 5_656 0.19(18) ?
C4 N1 Ni1 N2 . . . 5_656 178.2(2) ?
C1 N1 Ni1 N2 . . . . -179.81(18) ?
C4 N1 Ni1 N2 . . . . -1.8(2) ?
N1 C1 C2 C3 . . . . -0.4(3) ?
C9 C1 C2 C3 5_656 . . . 178.3(3) ?
C1 C2 C3 C4 . . . . 0.2(3) ?
C1 N1 C4 C3 . . . . -0.3(3) ?
Ni1 N1 C4 C3 . . . . -178.42(17) ?
C1 N1 C4 C5 . . . . -179.6(2) ?
Ni1 N1 C4 C5 . . . . 2.3(3) ?
C2 C3 C4 N1 . . . . 0.1(3) ?
C2 C3 C4 C5 . . . . 179.2(3) ?
N1 Ni1 N2 C9 5_656 . . . 0.02(18) ?
N1 Ni1 N2 C9 . . . . -179.98(18) ?
N1 Ni1 N2 C6 5_656 . . . -179.8(2) ?
N1 Ni1 N2 C6 . . . . 0.2(2) ?
N1 C4 C5 C6 . . . . -0.9(4) ?
C3 C4 C5 C6 . . . . -180.0(3) ?
N1 C4 C5 C10 . . . . 177.2(2) ?
C3 C4 C5 C10 . . . . -1.8(4) ?
C9 N2 C6 C7 . . . . 0.7(3) ?
Ni1 N2 C6 C7 . . . . -179.49(18) ?
C9 N2 C6 C5 . . . . -179.1(2) ?
Ni1 N2 C6 C5 . . . . 0.8(4) ?
C4 C5 C6 N2 . . . . -0.5(4) ?
C10 C5 C6 N2 . . . . -178.7(2) ?
C4 C5 C6 C7 . . . . 179.8(3) ?
C10 C5 C6 C7 . . . . 1.7(4) ?
N2 C6 C7 C8 . . . . -0.9(3) ?
C5 C6 C7 C8 . . . . 178.8(3) ?
C6 C7 C8 C9 . . . . 0.9(3) ?
C6 N2 C9 C8 . . . . -0.1(3) ?
Ni1 N2 C9 C8 . . . . 179.99(16) ?
C6 N2 C9 C1 . . . 5_656 180.0(2) ?
Ni1 N2 C9 C1 . . . 5_656 0.1(3) ?
C7 C8 C9 N2 . . . . -0.5(3) ?
C7 C8 C9 C1 . . . 5_656 179.3(3) ?

