#------------------------------------------------------------------------------
#$Date: 2025-08-22 18:52:37 +0300 (Fri, 22 Aug 2025) $
#$Revision: 301865 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/22/82/7228220.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7228220
loop_
_publ_author_name
'Carter, Damien J.'
'Raiteri, Paolo'
'Barnard, Keith R.'
'Gielink, Rhian'
'Mocerino, Mauro'
'Skelton, Brian W.'
'Vaughan, Jamila G.'
'Ogden, Mark I.'
'Rohl, Andrew L.'
_publ_section_title
;
 Difference Hirshfeld fingerprint plots: a tool for studying polymorphs
;
_journal_issue                   16
_journal_name_full               CrystEngComm
_journal_page_first              2207
_journal_paper_doi               10.1039/C6CE02535H
_journal_volume                  19
_journal_year                    2017
_chemical_formula_moiety         'C18 H20 N2 Ni O4'
_chemical_formula_sum            'C18 H20 N2 Ni O4'
_chemical_formula_weight         387.07
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2010-07-12T21:35:35-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_update_record
;
2016-11-25 deposited with the CCDC.
2017-03-28 downloaded from the CCDC.
;
_cell_angle_alpha                97.267(17)
_cell_angle_beta                 109.253(18)
_cell_angle_gamma                96.531(17)
_cell_formula_units_Z            1
_cell_length_a                   6.4680(13)
_cell_length_b                   7.7544(16)
_cell_length_c                   8.6026(17)
_cell_measurement_reflns_used    3385
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      37.0518
_cell_measurement_theta_min      3.3504
_cell_volume                     398.46(15)
_computing_cell_refinement
;
        CrysAlisPro, Oxford Diffraction Ltd.,
        Version 1.171.33.52 (release 06-11-2009 CrysAlis171 .NET)
        (compiled Nov  6 2009,16:24:50)
;
_computing_data_collection
;
        CrysAlisPro, Oxford Diffraction Ltd.,
        Version 1.171.33.52 (release 06-11-2009 CrysAlis171 .NET)
        (compiled Nov  6 2009,16:24:50)
;
_computing_data_reduction
;
        CrysAlisPro, Oxford Diffraction Ltd.,
        Version 1.171.33.52 (release 06-11-2009 CrysAlis171 .NET)
        (compiled Nov  6 2009,16:24:50)
;
_computing_molecular_graphics    'Diamond (Brandenburg, K., (1999)'
_computing_publication_material  'WinGX Farrugia, L. J. (1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SIR92 (Altomare et al., 1994)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 16.0009
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.965
_diffrn_measurement_device_type  'Oxford Diffraction Xcalibur, Sapphire3'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0642063828
_diffrn_orient_matrix_UB_12      -0.0051130175
_diffrn_orient_matrix_UB_13      -0.0524411853
_diffrn_orient_matrix_UB_21      -0.0603262628
_diffrn_orient_matrix_UB_22      -0.0854840762
_diffrn_orient_matrix_UB_23      -0.0401692017
_diffrn_orient_matrix_UB_31      -0.0783603844
_diffrn_orient_matrix_UB_32      0.0378934698
_diffrn_orient_matrix_UB_33      -0.0589048998
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0295
_diffrn_reflns_av_unetI/netI     0.0715
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            7581
_diffrn_reflns_theta_full        36.5
_diffrn_reflns_theta_max         37.22
_diffrn_reflns_theta_min         3.36
_exptl_absorpt_coefficient_mu    1.244
_exptl_absorpt_correction_T_max  0.904
_exptl_absorpt_correction_T_min  0.728
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
         CrysAlisPro, Oxford Diffraction Ltd.,
        Version 1.171.33.52 (release 06-11-2009 CrysAlis171 .NET)
        (compiled Nov  6 2009,16:24:50)
Analytical numeric absorption correction using a multifaceted crystal
                        model based on expressions derived by R.C. Clark & J.S.
        (Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
;
_exptl_crystal_colour            green
_exptl_crystal_density_diffrn    1.613
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             202
_exptl_crystal_size_max          0.39
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.89
_refine_diff_density_min         -0.761
_refine_diff_density_rms         0.104
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.941
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     118
_refine_ls_number_reflns         3960
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.941
_refine_ls_R_factor_all          0.0572
_refine_ls_R_factor_gt           0.0401
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0379P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0809
_refine_ls_wR_factor_ref         0.0841
_reflns_number_gt                2962
_reflns_number_total             3960
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            c6ce02535h2.cif
_cod_data_source_block           mjm433b
_cod_original_cell_volume        398.46(14)
_cod_original_sg_symbol_Hall     -p_1
_cod_database_code               7228220
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
Ni1 Ni 0 0 0 0.01413(7) Uani 1 2 d S
C1 C 0.4867(2) 0.21928(17) 0.04233(16) 0.0141(2) Uani 1 1 d .
C11 C 0.3147(2) 0.18324(17) -0.12457(16) 0.0146(2) Uani 1 1 d .
C12 C 0.3693(2) 0.23940(18) -0.26906(17) 0.0179(3) Uani 1 1 d .
H12A H 0.2524 0.1813 -0.3741 0.027 Uiso 1 1 calc R
H12B H 0.5117 0.2061 -0.2671 0.027 Uiso 1 1 calc R
H12C H 0.3794 0.3675 -0.2604 0.027 Uiso 1 1 calc R
N1 N 0.11595(19) 0.10514(15) -0.14631(13) 0.0144(2) Uani 1 1 d .
O1 O -0.03284(16) 0.08784(13) -0.30978(11) 0.01831(19) Uani 1 1 d .
H1 H -0.1551 0.03 -0.3182 0.027 Uiso 1 1 calc R
C2 C 0.4509(2) 0.16441(17) 0.18277(16) 0.0151(2) Uani 1 1 d .
O2 O 0.26045(15) 0.07164(13) 0.17585(11) 0.01712(19) Uani 1 1 d .
C3 C 0.6244(2) 0.20688(18) 0.33805(16) 0.0164(2) Uani 1 1 d .
H3 H 0.5999 0.1728 0.4336 0.02 Uiso 1 1 calc R
C4 C 0.8298(2) 0.29694(17) 0.35562(17) 0.0165(2) Uani 1 1 d .
H4 H 0.9444 0.322 0.4622 0.02 Uiso 1 1 calc R
C5 C 0.8709(2) 0.35145(17) 0.21900(17) 0.0159(2) Uani 1 1 d .
C6 C 0.6982(2) 0.31162(17) 0.06594(17) 0.0157(2) Uani 1 1 d .
H6 H 0.7242 0.3487 -0.0281 0.019 Uiso 1 1 calc R
C7 C 1.0944(2) 0.45212(18) 0.23714(18) 0.0190(3) Uani 1 1 d .
H7A H 1.1305 0.4151 0.1372 0.028 Uiso 1 1 calc R
H7B H 1.2085 0.4277 0.3358 0.028 Uiso 1 1 calc R
H7C H 1.0892 0.5788 0.2501 0.028 Uiso 1 1 calc R
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 0 '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 0.006 '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'
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-1 2 1 0.0516
1 -2 -1 0.1086
1 0 -1 0.1351
-1 0 1 0.182
0 -1 0 0.0788
0 1 0 0.0366
0 0 -1 0.0653
0 0 1 0.0392
0 1 -1 0.0435
0 -1 1 0.0573
1 -2 2 0.0868
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
O2 Ni1 O2 180.00(9) 2 .
O2 Ni1 N1 92.23(5) 2 2
O2 Ni1 N1 87.77(5) . 2
O2 Ni1 N1 87.77(5) 2 .
O2 Ni1 N1 92.23(5) . .
N1 Ni1 N1 180 2 .
C6 C1 C2 117.59(12) . .
C6 C1 C11 119.60(12) . .
C2 C1 C11 122.81(12) . .
N1 C11 C1 120.11(12) . .
N1 C11 C12 120.41(12) . .
C1 C11 C12 119.47(12) . .
C11 C12 H12A 109.5 . .
C11 C12 H12B 109.5 . .
H12A C12 H12B 109.5 . .
C11 C12 H12C 109.5 . .
H12A C12 H12C 109.5 . .
H12B C12 H12C 109.5 . .
C11 N1 O1 113.67(11) . .
C11 N1 Ni1 131.25(9) . .
O1 N1 Ni1 114.96(8) . .
N1 O1 H1 109.5 . .
O2 C2 C3 117.79(12) . .
O2 C2 C1 123.38(12) . .
C3 C2 C1 118.82(12) . .
C2 O2 Ni1 129.88(9) . .
C4 C3 C2 121.73(12) . .
C4 C3 H3 119.1 . .
C2 C3 H3 119.1 . .
C3 C4 C5 120.78(12) . .
C3 C4 H4 119.6 . .
C5 C4 H4 119.6 . .
C6 C5 C4 117.45(12) . .
C6 C5 C7 121.29(12) . .
C4 C5 C7 121.26(12) . .
C5 C6 C1 123.61(12) . .
C5 C6 H6 118.2 . .
C1 C6 H6 118.2 . .
C5 C7 H7A 109.5 . .
C5 C7 H7B 109.5 . .
H7A C7 H7B 109.5 . .
C5 C7 H7C 109.5 . .
H7A C7 H7C 109.5 . .
H7B C7 H7C 109.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Ni1 O2 1.8245(11) 2
Ni1 O2 1.8245(11) .
Ni1 N1 1.8853(12) 2
Ni1 N1 1.8853(12) .
C1 C6 1.4083(19) .
C1 C2 1.4094(18) .
C1 C11 1.4668(18) .
C11 N1 1.3000(18) .
C11 C12 1.5003(18) .
C12 H12A 0.98 .
C12 H12B 0.98 .
C12 H12C 0.98 .
N1 O1 1.3972(14) .
O1 H1 0.84 .
C2 O2 1.3332(16) .
C2 C3 1.4030(19) .
C3 C4 1.3802(19) .
C3 H3 0.95 .
C4 C5 1.3917(19) .
C4 H4 0.95 .
C5 C6 1.3875(19) .
C5 C7 1.5127(19) .
C6 H6 0.95 .
C7 H7A 0.98 .
C7 H7B 0.98 .
C7 H7C 0.98 .
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
O1 H1 O2 0.84 1.8 2.4676(14) 134.6 2
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139203482
