#------------------------------------------------------------------------------
#$Date: 2025-08-19 12:43:10 +0200 (Tue 19 de Aug de 2025) $
#$Revision: 301803 $
#$URL: svn://www.crystallography.net/cod/cif/2/20/61/2206125.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2206125
loop_
_publ_author_name
'Ma, Ji-Long'
'You, Zhong-Lu'
'Zhu, Hai-Liang'
_publ_section_title
cyclo-Tetrakis{μ-1-[2-(2-oxidoethylamino)ethyliminomethyl]naphthalen-2-olato}tetranickel(II)
_journal_issue                   7
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              m1258
_journal_page_last               m1260
_journal_paper_doi               10.1107/S1600536805017058
_journal_volume                  61
_journal_year                    2005
_chemical_formula_iupac          '[Ni4 (C15 H16 N2 O2)4]'
_chemical_formula_moiety         'C60 H64 N8 Ni4 O8'
_chemical_formula_sum            'C60 H64 N8 Ni4 O8'
_chemical_formula_weight         1260.03
_chemical_name_systematic
;
cyclo-Tetrakis{μ-1-[2-(2-oxidoethylamino)ethyliminomethyl]naphthalen-2-
olato}tetranickel(II)
;
_space_group_IT_number           86
_symmetry_cell_setting           tetragonal
_symmetry_space_group_name_Hall  '-P 4bc'
_symmetry_space_group_name_H-M   'P 42/n :2'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   18.1814(8)
_cell_length_b                   18.1814(8)
_cell_length_c                   8.5460(7)
_cell_measurement_reflns_used    1898
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      22.37
_cell_measurement_theta_min      2.12
_cell_volume                     2825.0(3)
_computing_cell_refinement       SMART
_computing_data_collection       'SMART (Bruker, 1998)'
_computing_data_reduction        'SAINT (Bruker, 1998)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 1997b)'
_computing_publication_material  SHELXTL
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997a)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997a)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker SMART CCD area-detector'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0413
_diffrn_reflns_av_sigmaI/netI    0.0374
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_number            12894
_diffrn_reflns_theta_full        26.49
_diffrn_reflns_theta_max         26.49
_diffrn_reflns_theta_min         1.58
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.375
_exptl_absorpt_correction_T_max  0.7518
_exptl_absorpt_correction_T_min  0.6521
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            green
_exptl_crystal_density_diffrn    1.481
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1312
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.22
_refine_diff_density_max         0.401
_refine_diff_density_min         -0.380
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     184
_refine_ls_number_reflns         2917
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.056
_refine_ls_R_factor_all          0.0621
_refine_ls_R_factor_gt           0.0486
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w = 1/[σ²(Fo²)+(0.0637P)²+1.4827P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1156
_refine_ls_wR_factor_ref         0.1233
_reflns_number_gt                2333
_reflns_number_total             2917
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            br6196.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Tetragonal' changed to 'tetragonal'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 

The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Tetragonal' changed to 'tetragonal'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_H-M      'P 42/n'
_cod_database_code               2206125
_cod_database_fobs_code          2206125
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y+1/2, z'
'-y, x+1/2, z+1/2'
'y+1/2, -x, z+1/2'
'-x, -y, -z'
'x-1/2, y-1/2, -z'
'y, -x-1/2, -z-1/2'
'-y-1/2, x, -z-1/2'
loop_
_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
_atom_site_occupancy
_atom_site_type_symbol
Ni1 0.80929(2) 0.62242(2) 0.22739(5) 0.03188(16) Uani d . 1 Ni
O1 0.76479(11) 0.58192(11) 0.0287(3) 0.0358(5) Uani d . 1 O
O2 0.71257(11) 0.63713(12) 0.3366(2) 0.0338(5) Uani d . 1 O
N1 0.87882(14) 0.53371(14) 0.2209(3) 0.0349(6) Uani d . 1 N
N2 0.84955(14) 0.62482(13) 0.4668(3) 0.0330(6) Uani d D 1 N
C1 0.84331(15) 0.47916(16) -0.0281(4) 0.0299(6) Uani d . 1 C
C2 0.78005(16) 0.52376(16) -0.0515(4) 0.0305(6) Uani d . 1 C
C3 0.72853(18) 0.50169(18) -0.1686(4) 0.0379(7) Uani d . 1 C
H3 0.6867 0.5301 -0.1845 0.045 Uiso calc R 1 H
C4 0.7384(2) 0.44118(19) -0.2568(4) 0.0427(8) Uani d . 1 C
H4 0.7020 0.4273 -0.3272 0.051 Uiso calc R 1 H
C5 0.8033(2) 0.39821(18) -0.2444(4) 0.0402(8) Uani d . 1 C
C6 0.8140(2) 0.3371(2) -0.3437(5) 0.0583(10) Uani d . 1 C
H6 0.7777 0.3241 -0.4152 0.070 Uiso calc R 1 H
C7 0.8769(3) 0.2970(2) -0.3356(6) 0.0718(13) Uani d . 1 C
H7 0.8835 0.2565 -0.4006 0.086 Uiso calc R 1 H
C8 0.9313(3) 0.3166(3) -0.2304(5) 0.0664(12) Uani d . 1 C
H8 0.9745 0.2894 -0.2264 0.080 Uiso calc R 1 H
C9 0.9225(2) 0.3756(2) -0.1317(4) 0.0480(9) Uani d . 1 C
H9 0.9602 0.3879 -0.0630 0.058 Uiso calc R 1 H
C10 0.85714(17) 0.41797(16) -0.1327(4) 0.0331(7) Uani d . 1 C
C11 0.88714(17) 0.48664(16) 0.1097(4) 0.0355(7) Uani d . 1 C
H11 0.9261 0.4538 0.1203 0.043 Uiso calc R 1 H
C12 0.92493(18) 0.5275(2) 0.3612(4) 0.0438(8) Uani d . 1 C
H12A 0.9682 0.5583 0.3508 0.053 Uiso calc R 1 H
H12B 0.9408 0.4769 0.3751 0.053 Uiso calc R 1 H
C13 0.87991(18) 0.55172(18) 0.4995(4) 0.0396(8) Uani d . 1 C
H13A 0.8403 0.5170 0.5180 0.048 Uiso calc R 1 H
H13B 0.9105 0.5535 0.5924 0.048 Uiso calc R 1 H
C14 0.78796(18) 0.64689(18) 0.5671(4) 0.0379(7) Uani d . 1 C
H14A 0.7861 0.7001 0.5749 0.046 Uiso calc R 1 H
H14B 0.7946 0.6269 0.6714 0.046 Uiso calc R 1 H
C15 0.71712(17) 0.61839(19) 0.4975(4) 0.0370(7) Uani d . 1 C
H15A 0.7150 0.5654 0.5091 0.044 Uiso calc R 1 H
H15B 0.6756 0.6394 0.5532 0.044 Uiso calc R 1 H
H2 0.8859(16) 0.6576(18) 0.473(5) 0.080 Uiso d D 1 H
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'
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
O2 Ni1 O2 8_756 . 116.62(12) y
O2 Ni1 O1 8_756 . 105.45(9) y
O2 Ni1 O1 . . 95.07(9) y
O2 Ni1 N1 8_756 . 109.87(10) y
O2 Ni1 N1 . . 131.08(10) y
O1 Ni1 N1 . . 86.42(9) y
O2 Ni1 N2 8_756 . 94.45(9) y
O2 Ni1 N2 . . 81.65(9) y
O1 Ni1 N2 . . 158.99(9) y
N1 Ni1 N2 . . 80.41(10) y
C2 O1 Ni1 . . 131.24(19) ?
C15 O2 Ni1 . 7_576 115.67(18) ?
C15 O2 Ni1 . . 111.54(17) ?
Ni1 O2 Ni1 7_576 . 131.35(11) ?
C11 N1 C12 . . 119.0(3) ?
C11 N1 Ni1 . . 128.0(2) ?
C12 N1 Ni1 . . 113.0(2) ?
C14 N2 C13 . . 115.1(3) ?
C14 N2 Ni1 . . 107.37(18) ?
C13 N2 Ni1 . . 106.74(19) ?
C14 N2 H2 . . 110(3) ?
C13 N2 H2 . . 108(3) ?
Ni1 N2 H2 . . 109(3) ?
C2 C1 C11 . . 120.9(3) ?
C2 C1 C10 . . 119.4(3) ?
C11 C1 C10 . . 119.0(3) ?
O1 C2 C1 . . 124.5(3) ?
O1 C2 C3 . . 117.5(3) ?
C1 C2 C3 . . 118.0(3) ?
C4 C3 C2 . . 122.3(3) ?
C4 C3 H3 . . 118.8 ?
C2 C3 H3 . . 118.8 ?
C3 C4 C5 . . 121.3(3) ?
C3 C4 H4 . . 119.3 ?
C5 C4 H4 . . 119.3 ?
C6 C5 C10 . . 120.7(3) ?
C6 C5 C4 . . 120.3(3) ?
C10 C5 C4 . . 119.1(3) ?
C7 C6 C5 . . 120.5(4) ?
C7 C6 H6 . . 119.7 ?
C5 C6 H6 . . 119.7 ?
C6 C7 C8 . . 119.8(4) ?
C6 C7 H7 . . 120.1 ?
C8 C7 H7 . . 120.1 ?
C9 C8 C7 . . 121.2(4) ?
C9 C8 H8 . . 119.4 ?
C7 C8 H8 . . 119.4 ?
C8 C9 C10 . . 121.2(4) ?
C8 C9 H9 . . 119.4 ?
C10 C9 H9 . . 119.4 ?
C5 C10 C9 . . 116.6(3) ?
C5 C10 C1 . . 119.4(3) ?
C9 C10 C1 . . 124.0(3) ?
N1 C11 C1 . . 127.3(3) ?
N1 C11 H11 . . 116.3 ?
C1 C11 H11 . . 116.3 ?
N1 C12 C13 . . 108.0(3) ?
N1 C12 H12A . . 110.1 ?
C13 C12 H12A . . 110.1 ?
N1 C12 H12B . . 110.1 ?
C13 C12 H12B . . 110.1 ?
H12A C12 H12B . . 108.4 ?
N2 C13 C12 . . 108.7(3) ?
N2 C13 H13A . . 109.9 ?
C12 C13 H13A . . 109.9 ?
N2 C13 H13B . . 109.9 ?
C12 C13 H13B . . 109.9 ?
H13A C13 H13B . . 108.3 ?
N2 C14 C15 . . 109.1(3) ?
N2 C14 H14A . . 109.9 ?
C15 C14 H14A . . 109.9 ?
N2 C14 H14B . . 109.9 ?
C15 C14 H14B . . 109.9 ?
H14A C14 H14B . . 108.3 ?
O2 C15 C14 . . 110.4(3) ?
O2 C15 H15A . . 109.6 ?
C14 C15 H15A . . 109.6 ?
O2 C15 H15B . . 109.6 ?
C14 C15 H15B . . 109.6 ?
H15A C15 H15B . . 108.1 ?
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 O2 8_756 1.984(2) y
Ni1 O2 . 2.009(2) y
Ni1 O1 . 2.020(2) y
Ni1 N1 . 2.050(3) y
Ni1 N2 . 2.174(3) y
O1 C2 . 1.290(3) ?
O2 C15 . 1.419(4) ?
O2 Ni1 7_576 1.984(2) ?
N1 C11 . 1.288(4) ?
N1 C12 . 1.467(4) ?
N2 C14 . 1.466(4) ?
N2 C13 . 1.466(4) ?
N2 H2 . 0.892(10) ?
C1 C2 . 1.421(4) ?
C1 C11 . 1.428(4) ?
C1 C10 . 1.449(4) ?
C2 C3 . 1.428(4) ?
C3 C4 . 1.346(5) ?
C3 H3 . 0.9300 ?
C4 C5 . 1.418(5) ?
C4 H4 . 0.9300 ?
C5 C6 . 1.412(5) ?
C5 C10 . 1.414(5) ?
C6 C7 . 1.358(6) ?
C6 H6 . 0.9300 ?
C7 C8 . 1.382(7) ?
C7 H7 . 0.9300 ?
C8 C9 . 1.374(6) ?
C8 H8 . 0.9300 ?
C9 C10 . 1.417(4) ?
C9 H9 . 0.9300 ?
C11 H11 . 0.9300 ?
C12 C13 . 1.504(5) ?
C12 H12A . 0.9700 ?
C12 H12B . 0.9700 ?
C13 H13A . 0.9700 ?
C13 H13B . 0.9700 ?
C14 C15 . 1.510(4) ?
C14 H14A . 0.9700 ?
C14 H14B . 0.9700 ?
C15 H15A . 0.9700 ?
C15 H15B . 0.9700 ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 168308857
