# Supplementary Information (SI) for Chemical Communications.
# This journal is © The Royal Society of Chemistry 2024

####################################################################### 
# 
# 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_CEC0276_1
_database_code_depnum_ccdc_archive 'CCDC 2374778'
loop_
_audit_author_name
_audit_author_address
'Thomas Weyhermueller'
;Max Planck Institute for Chemical Energy Conversion
Germany
;
_audit_update_record             
;
2024-07-31 deposited with the CCDC.	2024-11-22 downloaded from the CCDC.
;
_audit_creation_method           'APEX4 v2022.1-1'
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         'C17 H14 N2 Ni O'
_chemical_formula_sum            'C17 H14 N2 Ni O'
_chemical_formula_iupac          ?
_chemical_formula_weight         321.01

_chemical_melting_point          ?

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   6.8635(3)
_cell_length_b                   22.7679(9)
_cell_length_c                   8.8158(3)
_cell_angle_alpha                90
_cell_angle_beta                 94.763(2)
_cell_angle_gamma                90
_cell_volume                     1372.87(9)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9985
_cell_measurement_theta_min      2.4849
_cell_measurement_theta_max      36.2814
_cell_measurement_temperature    85(2)

_exptl_crystal_description       fragment
_exptl_crystal_colour            'lustrous dark green'
_exptl_crystal_size_max          0.065
_exptl_crystal_size_mid          0.050
_exptl_crystal_size_min          0.050
_exptl_crystal_density_diffrn    1.553
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             664

_exptl_absorpt_coefficient_mu    1.412
_exptl_absorpt_correction_type   Multi-Scan
_exptl_absorpt_process_details   
;
Krause, L., Herbst-Irmer, R., Sheldrick, G. M., Stalke, D. (2015).
"Comparison of silver and molybdenum microfocus X-ray sources for
single-crystal structure determination"
J. Appl. Cryst. 48, 3-10.
doi:10.1107/S1600576714022985
;
_exptl_absorpt_correction_T_min  0.85
_exptl_absorpt_correction_T_max  0.93

_exptl_special_details           
;
;

_diffrn_ambient_temperature      85(2)

_diffrn_source                   'microfocus sealed tube'
_diffrn_source_type              'INCOATEC I\mS DIAMOND'
_diffrn_source_power             0.07
_diffrn_source_current           1.4
_diffrn_source_voltage           50

_diffrn_radiation_probe          ?
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  'multilayer mirror'

_diffrn_measurement_device       'KAPPA diffractometer'
_diffrn_measurement_device_type  'Bruker D8 VENTURE'
_diffrn_measurement_method       'ω and φ scans'

_diffrn_detector_area_resol_mean 7.3910

_diffrn_reflns_number            88109
_diffrn_reflns_av_R_equivalents  0.0443
_diffrn_reflns_av_unetI/netI     0.0201
_diffrn_reflns_theta_min         2.48
_diffrn_reflns_theta_max         36.42
_diffrn_reflns_theta_full        25.24
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -38
_diffrn_reflns_limit_k_max       38
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14

_refine_special_details          
;
;

_reflns_number_total             6709
_reflns_number_gt                5923
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0352
_refine_ls_R_factor_gt           0.0293
_refine_ls_wR_factor_gt          0.0717
_refine_ls_wR_factor_ref         0.0743
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_restrained_S_all      1.066
_refine_ls_number_reflns         6709
_refine_ls_number_parameters     193
_refine_ls_number_restraints     0
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0322P)²+0.6329P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap

_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.624
_refine_diff_density_min         -0.385
_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'
O O 0.0106 0.0060 '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       'Bruker Instrument Service vV6.2.15'
_computing_cell_refinement       'SAINT V8.40B (Bruker AXS LLC, 2019)'
_computing_data_reduction        'SAINT V8.40B (Bruker AXS LLC, 2019)'
_computing_structure_solution    'XT, VERSION 2018/2'
_computing_structure_refinement  'SHELXL-2019/1 (Sheldrick, 2019)'
_computing_molecular_graphics    'shelXle (C.B. Huebschle, rev 1365)'
_computing_publication_material  ?

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
Ni Ni1 0.18423(2) 0.43714(2) 0.30668(2) 0.01360(3) Uani d . . . 1 . .
O O1 0.12903(12) 0.39507(4) 0.12799(8) 0.02048(14) Uani d . . . 1 . .
C C2 0.16064(15) 0.35746(4) 0.24474(11) 0.01734(16) Uani d . . . 1 . .
H H2 0.047(2) 0.3375(7) 0.2826(18) 0.021000 Uiso d U . . 1 . .
C C3 0.34339(14) 0.32306(4) 0.26416(10) 0.01514(15) Uani d . . . 1 . .
C C4 0.49438(15) 0.33032(4) 0.16794(11) 0.01664(15) Uani d . . . 1 . .
H H4 0.478276 0.357109 0.085239 0.020000 Uiso calc U . R 1 . .
C C5 0.66709(16) 0.29874(5) 0.19235(12) 0.01929(17) Uani d . . . 1 . .
H H5 0.767648 0.304063 0.125804 0.023000 Uiso calc U . R 1 . .
C C6 0.69506(16) 0.25928(5) 0.31331(12) 0.02033(17) Uani d . . . 1 . .
H H6 0.814243 0.238149 0.330114 0.024000 Uiso calc U . R 1 . .
C C7 0.54593(16) 0.25136(4) 0.40889(12) 0.01986(17) Uani d . . . 1 . .
H H7 0.563104 0.224615 0.491648 0.024000 Uiso calc U . R 1 . .
C C8 0.37163(15) 0.28243(4) 0.38384(12) 0.01800(16) Uani d . . . 1 . .
H H8 0.269966 0.276042 0.448819 0.022000 Uiso calc U . R 1 . .
N N11 0.24214(12) 0.45063(4) 0.51586(9) 0.01392(13) Uani d . . . 1 . .
C C12 0.25468(15) 0.40922(4) 0.62600(11) 0.01739(16) Uani d . . . 1 . .
H H12 0.236274 0.369232 0.597516 0.021000 Uiso calc U . R 1 . .
C C13 0.29322(16) 0.42267(5) 0.77861(11) 0.01976(17) Uani d . . . 1 . .
H H13 0.299241 0.392552 0.853436 0.024000 Uiso calc U . R 1 . .
C C14 0.32288(16) 0.48087(5) 0.82030(11) 0.02056(18) Uani d . . . 1 . .
H H14 0.351128 0.491105 0.924268 0.025000 Uiso calc U . R 1 . .
C C15 0.31094(15) 0.52410(5) 0.70880(11) 0.01864(16) Uani d . . . 1 . .
H H15 0.331213 0.564210 0.735292 0.022000 Uiso calc U . R 1 . .
C C16 0.26875(13) 0.50765(4) 0.55743(10) 0.01398(14) Uani d . . . 1 . .
C C17 0.24475(13) 0.54896(4) 0.42883(10) 0.01409(14) Uani d . . . 1 . .
C C18 0.26680(15) 0.60954(4) 0.44243(12) 0.01888(17) Uani d . . . 1 . .
H H18 0.303573 0.626890 0.538562 0.023000 Uiso calc U . R 1 . .
C C19 0.23420(17) 0.64424(5) 0.31317(13) 0.02155(18) Uani d . . . 1 . .
H H19 0.248728 0.685686 0.319445 0.026000 Uiso calc U . R 1 . .
C C20 0.18004(16) 0.61737(5) 0.17471(12) 0.01986(17) Uani d . . . 1 . .
H H20 0.156157 0.640166 0.084830 0.024000 Uiso calc U . R 1 . .
C C21 0.16135(15) 0.55682(4) 0.16961(11) 0.01698(15) Uani d . . . 1 . .
H H21 0.123715 0.538696 0.074604 0.020000 Uiso calc U . R 1 . .
N N22 0.19415(12) 0.52263(4) 0.29322(9) 0.01439(13) 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
Ni1 O1 . 1.8557(7) ?
Ni1 N11 . 1.8791(8) ?
Ni1 C2 . 1.8977(10) ?
Ni1 N22 . 1.9517(9) ?
O1 C2 . 1.3426(13) ?
C2 C3 . 1.4766(14) ?
C3 C4 . 1.4025(14) ?
C3 C8 . 1.4045(14) ?
C4 C5 . 1.3878(15) ?
C5 C6 . 1.3953(15) ?
C6 C7 . 1.3906(15) ?
C7 C8 . 1.3916(15) ?
N11 C12 . 1.3510(12) ?
N11 C16 . 1.3572(12) ?
C12 C13 . 1.3837(14) ?
C13 C14 . 1.3856(16) ?
C14 C15 . 1.3887(15) ?
C15 C16 . 1.3931(13) ?
C16 C17 . 1.4719(13) ?
C17 N22 . 1.3565(12) ?
C17 C18 . 1.3915(14) ?
C18 C19 . 1.3894(15) ?
C19 C20 . 1.3882(16) ?
C20 C21 . 1.3849(15) ?
C21 N22 . 1.3429(12) ?

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
O1 Ni1 N11 . . 158.29(4) ?
O1 Ni1 C2 . . 41.90(4) ?
N11 Ni1 C2 . . 116.40(4) ?
O1 Ni1 N22 . . 117.96(3) ?
N11 Ni1 N22 . . 83.75(3) ?
C2 Ni1 N22 . . 159.81(4) ?
C2 O1 Ni1 . . 70.72(5) ?
O1 C2 C3 . . 120.59(9) ?
O1 C2 Ni1 . . 67.37(5) ?
C3 C2 Ni1 . . 114.98(7) ?
C4 C3 C8 . . 117.98(9) ?
C4 C3 C2 . . 122.05(9) ?
C8 C3 C2 . . 119.96(9) ?
C5 C4 C3 . . 120.64(9) ?
C4 C5 C6 . . 120.90(10) ?
C7 C6 C5 . . 119.02(10) ?
C6 C7 C8 . . 120.28(9) ?
C7 C8 C3 . . 121.15(9) ?
C12 N11 C16 . . 118.32(8) ?
C12 N11 Ni1 . . 125.94(7) ?
C16 N11 Ni1 . . 115.72(6) ?
N11 C12 C13 . . 122.68(10) ?
C12 C13 C14 . . 118.79(10) ?
C13 C14 C15 . . 119.43(9) ?
C14 C15 C16 . . 118.87(10) ?
N11 C16 C15 . . 121.90(9) ?
N11 C16 C17 . . 113.54(8) ?
C15 C16 C17 . . 124.55(9) ?
N22 C17 C18 . . 122.14(9) ?
N22 C17 C16 . . 113.61(8) ?
C18 C17 C16 . . 124.24(9) ?
C19 C18 C17 . . 118.95(9) ?
C20 C19 C18 . . 118.92(10) ?
C21 C20 C19 . . 118.98(9) ?
N22 C21 C20 . . 122.80(9) ?
C21 N22 C17 . . 118.19(9) ?
C21 N22 Ni1 . . 128.54(7) ?
C17 N22 Ni1 . . 113.26(6) ?

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
N11 Ni1 O1 C2 . . . . -2.38(13) ?
N22 Ni1 O1 C2 . . . . 178.19(6) ?
Ni1 O1 C2 C3 . . . . -106.57(9) ?
N11 Ni1 C2 O1 . . . . 179.02(5) ?
N22 Ni1 C2 O1 . . . . -4.63(14) ?
O1 Ni1 C2 C3 . . . . 114.45(10) ?
N11 Ni1 C2 C3 . . . . -66.53(8) ?
N22 Ni1 C2 C3 . . . . 109.82(12) ?
O1 C2 C3 C4 . . . . 3.48(14) ?
Ni1 C2 C3 C4 . . . . -73.95(10) ?
O1 C2 C3 C8 . . . . -177.86(9) ?
Ni1 C2 C3 C8 . . . . 104.71(9) ?
C8 C3 C4 C5 . . . . -0.89(14) ?
C2 C3 C4 C5 . . . . 177.80(9) ?
C3 C4 C5 C6 . . . . -0.28(15) ?
C4 C5 C6 C7 . . . . 0.75(15) ?
C5 C6 C7 C8 . . . . -0.01(15) ?
C6 C7 C8 C3 . . . . -1.20(15) ?
C4 C3 C8 C7 . . . . 1.63(14) ?
C2 C3 C8 C7 . . . . -177.08(9) ?
O1 Ni1 N11 C12 . . . . -3.16(15) ?
C2 Ni1 N11 C12 . . . . -4.94(10) ?
N22 Ni1 N11 C12 . . . . 176.33(9) ?
O1 Ni1 N11 C16 . . . . 178.43(9) ?
C2 Ni1 N11 C16 . . . . 176.66(7) ?
N22 Ni1 N11 C16 . . . . -2.07(7) ?
C16 N11 C12 C13 . . . . 0.05(14) ?
Ni1 N11 C12 C13 . . . . -178.32(8) ?
N11 C12 C13 C14 . . . . -0.91(16) ?
C12 C13 C14 C15 . . . . 0.77(15) ?
C13 C14 C15 C16 . . . . 0.17(15) ?
C12 N11 C16 C15 . . . . 0.95(14) ?
Ni1 N11 C16 C15 . . . . 179.48(7) ?
C12 N11 C16 C17 . . . . -177.91(8) ?
Ni1 N11 C16 C17 . . . . 0.62(10) ?
C14 C15 C16 N11 . . . . -1.07(14) ?
C14 C15 C16 C17 . . . . 177.66(9) ?
N11 C16 C17 N22 . . . . 2.06(11) ?
C15 C16 C17 N22 . . . . -176.76(9) ?
N11 C16 C17 C18 . . . . -179.28(9) ?
C15 C16 C17 C18 . . . . 1.89(15) ?
N22 C17 C18 C19 . . . . 0.60(15) ?
C16 C17 C18 C19 . . . . -177.94(9) ?
C17 C18 C19 C20 . . . . 0.21(16) ?
C18 C19 C20 C21 . . . . -0.38(16) ?
C19 C20 C21 N22 . . . . -0.26(16) ?
C20 C21 N22 C17 . . . . 1.04(14) ?
C20 C21 N22 Ni1 . . . . -177.63(8) ?
C18 C17 N22 C21 . . . . -1.22(14) ?
C16 C17 N22 C21 . . . . 177.47(8) ?
C18 C17 N22 Ni1 . . . . 177.65(8) ?
C16 C17 N22 Ni1 . . . . -3.66(10) ?



_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
_chemical_properties_physical    
Air-sensitive,Moisture-sensitive,Oxygen-sensitive
