#------------------------------------------------------------------------------
#$Date: 2025-08-20 21:19:29 +0200 (Wed 20 de Aug de 2025) $
#$Revision: 301836 $
#$URL: svn://www.crystallography.net/cod/cif/4/30/24/4302475.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_4302475
loop_
_publ_author_name
'Michael Frezza'
'Sarmad Sahiel Hindo'
'Dajena Tomco'
'Marco M. Allard'
'Qiuzhi Cindy Cui'
'Mary Jane Heeg'
'Di Chen'
'Cláudio N. Verani'
'Q. Ping Dou'
_publ_contact_author_address
;    Department of Chemistry
     Wayne State University
    Detroit, Michigan 48202
    USA
;
_publ_contact_author_email       cnverani@chem.wayne.edu
_publ_contact_author_name        '    Prof. Claudio N. Verani'
_publ_section_title
;
Comparative Activities of Nickel(II) and Zinc(II) Complexes of Asymmetric
[NN'O] Ligands as 26S Proteasome Inhibitors
;
_journal_name_full               'Inorganic Chemistry'
_journal_page_first              5928
_journal_page_last               5937
_journal_paper_doi               10.1021/ic900276g
_journal_volume                  48
_journal_year                    2009
_chemical_formula_sum            'C29 H25 Cl9 I4 N4 Ni O2'
_chemical_formula_weight         1346.89
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 92.8120(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   18.4231(5)
_cell_length_b                   10.1797(3)
_cell_length_c                   22.1493(6)
_cell_measurement_reflns_used    9905
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      28.0
_cell_measurement_theta_min      2.5
_cell_volume                     4148.9(2)
_computing_cell_refinement       'Bruker APEX2'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker APEX2'
_computing_molecular_graphics    SHELXTL-Plus
_computing_publication_material  SHELXL-97
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_method       'Bruker APEX2'
_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  0.0663
_diffrn_reflns_av_sigmaI/netI    0.0525
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            86456
_diffrn_reflns_theta_full        28.30
_diffrn_reflns_theta_max         28.32
_diffrn_reflns_theta_min         1.47
_exptl_absorpt_coefficient_mu    4.057
_exptl_absorpt_correction_T_max  0.7928
_exptl_absorpt_correction_T_min  0.5813
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    2.156
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plates
_exptl_crystal_F_000             2544
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.06
_refine_diff_density_max         1.246
_refine_diff_density_min         -0.890
_refine_diff_density_rms         0.153
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     442
_refine_ls_number_reflns         10307
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.045
_refine_ls_R_factor_all          0.0632
_refine_ls_R_factor_gt           0.0363
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0240P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0591
_refine_ls_wR_factor_ref         0.0644
_reflns_number_gt                7578
_reflns_number_total             10307
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ic900276g_si_002_2.cif
_cod_data_source_block           nsar
_cod_depositor_comments
;
The following automatic conversions were performed:
'_exptl_absorpt_correction_type' value 'Multi-scan' changed to
'multi-scan' 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 
;
_cod_database_code               4302475
loop_
_symmetry_equiv_pos_as_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'
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
_atom_site_disorder_assembly
_atom_site_disorder_group
I1 I -0.124734(15) -0.79697(2) 0.413060(12) 0.02416(7) Uani 1 1 d . . .
I2 I -0.249342(14) -0.37420(2) 0.247853(12) 0.02279(7) Uani 1 1 d . . .
I3 I 0.125535(15) 0.36196(2) 0.088927(12) 0.02390(7) Uani 1 1 d . . .
I4 I 0.245934(14) -0.09930(2) 0.233335(12) 0.02214(7) Uani 1 1 d . . .
Ni1 Ni -0.00147(3) -0.23748(4) 0.23982(2) 0.01275(10) Uani 1 1 d . . .
N1 N -0.02563(16) -0.2463(3) 0.33129(13) 0.0146(7) Uani 1 1 d . . .
C1 C -0.0821(2) -0.1940(3) 0.35889(17) 0.0194(9) Uani 1 1 d . . .
H1 H -0.1161 -0.1434 0.3352 0.023 Uiso 1 1 calc R . .
C2 C -0.0935(2) -0.2093(4) 0.41921(17) 0.0247(9) Uani 1 1 d . . .
H2 H -0.1341 -0.1697 0.4369 0.030 Uiso 1 1 calc R . .
C3 C -0.0441(2) -0.2843(4) 0.45368(18) 0.0297(11) Uani 1 1 d . . .
H3 H -0.0498 -0.2965 0.4957 0.036 Uiso 1 1 calc R . .
C4 C 0.0127(2) -0.3399(4) 0.42618(17) 0.0245(10) Uani 1 1 d . . .
H4 H 0.0466 -0.3928 0.4490 0.029 Uiso 1 1 calc R . .
C5 C 0.0215(2) -0.3197(3) 0.36476(16) 0.0166(8) Uani 1 1 d . . .
C6 C 0.0853(2) -0.3738(3) 0.33285(15) 0.0174(8) Uani 1 1 d . . .
H6A H 0.1272 -0.3137 0.3392 0.021 Uiso 1 1 calc R . .
H6B H 0.0991 -0.4600 0.3506 0.021 Uiso 1 1 calc R . .
N2 N 0.06861(16) -0.3897(3) 0.26734(13) 0.0134(7) Uani 1 1 d . . .
C7 C 0.03809(19) -0.5218(3) 0.25102(16) 0.0148(8) Uani 1 1 d . . .
H7A H 0.0724 -0.5907 0.2660 0.018 Uiso 1 1 calc R . .
H7B H 0.0327 -0.5295 0.2065 0.018 Uiso 1 1 calc R . .
C8 C -0.03430(19) -0.5435(3) 0.27748(15) 0.0127(8) Uani 1 1 d . . .
C9 C -0.0436(2) -0.6401(3) 0.32056(16) 0.0161(8) Uani 1 1 d . . .
H9 H -0.0037 -0.6934 0.3341 0.019 Uiso 1 1 calc R . .
C10 C -0.1117(2) -0.6587(3) 0.34395(16) 0.0155(8) Uani 1 1 d . . .
C11 C -0.1712(2) -0.5838(3) 0.32412(15) 0.0151(8) Uani 1 1 d . . .
H11 H -0.2177 -0.5984 0.3397 0.018 Uiso 1 1 calc R . .
C12 C -0.16142(19) -0.4870(3) 0.28104(15) 0.0134(8) Uani 1 1 d . . .
C13 C -0.0937(2) -0.4615(3) 0.25689(15) 0.0143(8) Uani 1 1 d . . .
O1 O -0.08431(13) -0.3670(2) 0.21780(10) 0.0151(5) Uani 1 1 d . . .
N3 N 0.02459(16) -0.2246(3) 0.14925(13) 0.0146(7) Uani 1 1 d . . .
C14 C 0.0832(2) -0.2723(3) 0.12317(17) 0.0198(9) Uani 1 1 d . . .
H14 H 0.1181 -0.3190 0.1479 0.024 Uiso 1 1 calc R . .
C15 C 0.0960(2) -0.2578(4) 0.06280(17) 0.0230(9) Uani 1 1 d . . .
H15 H 0.1383 -0.2934 0.0462 0.028 Uiso 1 1 calc R . .
C16 C 0.0449(2) -0.1890(4) 0.02688(18) 0.0287(10) Uani 1 1 d . . .
H16 H 0.0511 -0.1784 -0.0152 0.034 Uiso 1 1 calc R . .
C17 C -0.0153(2) -0.1361(3) 0.05341(17) 0.0244(10) Uani 1 1 d . . .
H17 H -0.0505 -0.0874 0.0299 0.029 Uiso 1 1 calc R . .
C18 C -0.0235(2) -0.1551(3) 0.11468(16) 0.0171(9) Uani 1 1 d . . .
C19 C -0.0879(2) -0.1020(3) 0.14620(16) 0.0191(9) Uani 1 1 d . . .
H19A H -0.1018 -0.0159 0.1284 0.023 Uiso 1 1 calc R . .
H19B H -0.1295 -0.1626 0.1394 0.023 Uiso 1 1 calc R . .
N4 N -0.07248(16) -0.0860(3) 0.21183(13) 0.0146(7) Uani 1 1 d . . .
C20 C -0.04314(19) 0.0460(3) 0.22931(16) 0.0158(8) Uani 1 1 d . . .
H20A H -0.0405 0.0530 0.2739 0.019 Uiso 1 1 calc R . .
H20B H -0.0772 0.1142 0.2134 0.019 Uiso 1 1 calc R . .
C21 C 0.0311(2) 0.0725(3) 0.20625(15) 0.0137(8) Uani 1 1 d . . .
C22 C 0.0423(2) 0.1771(3) 0.16770(16) 0.0172(8) Uani 1 1 d . . .
H22 H 0.0023 0.2305 0.1545 0.021 Uiso 1 1 calc R . .
C23 C 0.1103(2) 0.2044(3) 0.14831(16) 0.0171(8) Uani 1 1 d . . .
C24 C 0.1698(2) 0.1278(3) 0.16668(15) 0.0163(8) Uani 1 1 d . . .
H24 H 0.2169 0.1465 0.1533 0.020 Uiso 1 1 calc R . .
C25 C 0.15822(19) 0.0232(3) 0.20510(16) 0.0150(8) Uani 1 1 d . . .
C26 C 0.0899(2) -0.0092(3) 0.22630(16) 0.0146(8) Uani 1 1 d . . .
O2 O 0.08039(13) -0.1097(2) 0.26236(10) 0.0148(6) Uani 1 1 d . . .
H1N2 H 0.1162 -0.3965 0.2562 0.050 Uiso 1 1 d . . .
H1N4 H -0.1188 -0.0959 0.2367 0.050 Uiso 1 1 d . . .
C27 C 0.3663(2) 0.4970(3) 0.11684(17) 0.0226(9) Uani 1 1 d . . .
H27 H 0.3763 0.4520 0.1565 0.027 Uiso 1 1 calc R . .
Cl1 Cl 0.32977(6) 0.38142(10) 0.06499(5) 0.0305(3) Uani 1 1 d . . .
Cl2 Cl 0.44835(6) 0.56165(11) 0.09254(6) 0.0428(3) Uani 1 1 d . . .
Cl3 Cl 0.30368(7) 0.62513(10) 0.12739(6) 0.0469(3) Uani 1 1 d . . .
C28 C 0.1455(2) 0.5141(4) -0.10362(16) 0.0230(9) Uani 1 1 d . . .
H28 H 0.1495 0.4357 -0.1304 0.028 Uiso 1 1 calc R . .
Cl4 Cl 0.21224(6) 0.50204(10) -0.04408(4) 0.0280(2) Uani 1 1 d . . .
Cl5 Cl 0.05877(6) 0.51620(12) -0.07523(5) 0.0433(3) Uani 1 1 d . . .
Cl6 Cl 0.16049(8) 0.65624(10) -0.14629(5) 0.0455(4) Uani 1 1 d . . .
C29 C 0.2756(2) -0.0019(4) -0.01471(17) 0.0246(9) Uani 1 1 d . . .
H29 H 0.3180 0.0353 -0.0355 0.029 Uiso 1 1 calc R . .
Cl7 Cl 0.23242(6) -0.11876(9) -0.06284(5) 0.0296(3) Uani 1 1 d . . .
Cl8 Cl 0.21615(7) 0.12664(10) 0.00071(5) 0.0397(3) Uani 1 1 d . . .
Cl9 Cl 0.30796(7) -0.07866(12) 0.05211(5) 0.0481(3) Uani 1 1 d . . .
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'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 '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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O2 Ni1 O1 179.52(10) . . ?
O2 Ni1 N2 87.86(10) . . ?
O1 Ni1 N2 91.99(10) . . ?
O2 Ni1 N3 89.60(10) . . ?
O1 Ni1 N3 90.87(10) . . ?
N2 Ni1 N3 99.14(11) . . ?
O2 Ni1 N4 92.66(10) . . ?
O1 Ni1 N4 87.49(10) . . ?
N2 Ni1 N4 179.47(11) . . ?
N3 Ni1 N4 80.76(11) . . ?
O2 Ni1 N1 88.86(10) . . ?
O1 Ni1 N1 90.66(10) . . ?
N2 Ni1 N1 81.01(11) . . ?
N3 Ni1 N1 178.45(11) . . ?
N4 Ni1 N1 99.10(12) . . ?
C5 N1 C1 117.7(3) . . ?
C5 N1 Ni1 113.3(3) . . ?
C1 N1 Ni1 129.0(2) . . ?
N1 C1 C2 123.9(4) . . ?
C1 C2 C3 118.0(4) . . ?
C4 C3 C2 118.8(4) . . ?
C3 C4 C5 120.3(4) . . ?
N1 C5 C4 121.3(4) . . ?
N1 C5 C6 116.3(3) . . ?
C4 C5 C6 122.4(3) . . ?
N2 C6 C5 111.8(3) . . ?
C6 N2 C7 113.2(3) . . ?
C6 N2 Ni1 107.5(2) . . ?
C7 N2 Ni1 112.1(2) . . ?
N2 C7 C8 111.7(3) . . ?
C9 C8 C13 120.9(3) . . ?
C9 C8 C7 121.1(3) . . ?
C13 C8 C7 118.0(3) . . ?
C8 C9 C10 119.8(3) . . ?
C11 C10 C9 121.3(3) . . ?
C11 C10 I1 118.7(3) . . ?
C9 C10 I1 119.9(3) . . ?
C12 C11 C10 118.6(3) . . ?
C11 C12 C13 122.7(3) . . ?
C11 C12 I2 120.4(3) . . ?
C13 C12 I2 116.9(2) . . ?
O1 C13 C12 122.3(3) . . ?
O1 C13 C8 120.9(3) . . ?
C12 C13 C8 116.7(3) . . ?
C13 O1 Ni1 115.7(2) . . ?
C14 N3 C18 117.9(3) . . ?
C14 N3 Ni1 128.2(2) . . ?
C18 N3 Ni1 113.8(3) . . ?
N3 C14 C15 124.0(3) . . ?
C14 C15 C16 117.8(4) . . ?
C15 C16 C17 119.0(4) . . ?
C18 C17 C16 119.1(4) . . ?
N3 C18 C17 122.1(4) . . ?
N3 C18 C19 115.9(3) . . ?
C17 C18 C19 122.0(3) . . ?
N4 C19 C18 112.2(3) . . ?
C19 N4 C20 113.9(3) . . ?
C19 N4 Ni1 107.3(2) . . ?
C20 N4 Ni1 111.9(2) . . ?
N4 C20 C21 113.4(3) . . ?
C22 C21 C26 120.5(3) . . ?
C22 C21 C20 120.7(3) . . ?
C26 C21 C20 118.7(3) . . ?
C23 C22 C21 120.9(3) . . ?
C22 C23 C24 120.9(3) . . ?
C22 C23 I3 120.2(3) . . ?
C24 C23 I3 118.9(3) . . ?
C25 C24 C23 117.9(3) . . ?
C24 C25 C26 123.6(3) . . ?
C24 C25 I4 119.8(3) . . ?
C26 C25 I4 116.6(2) . . ?
O2 C26 C25 122.3(3) . . ?
O2 C26 C21 121.5(3) . . ?
C25 C26 C21 116.1(3) . . ?
C26 O2 Ni1 117.9(2) . . ?
Cl1 C27 Cl2 111.0(2) . . ?
Cl1 C27 Cl3 110.5(2) . . ?
Cl2 C27 Cl3 110.0(2) . . ?
Cl5 C28 Cl6 110.8(2) . . ?
Cl5 C28 Cl4 110.4(2) . . ?
Cl6 C28 Cl4 109.7(2) . . ?
Cl8 C29 Cl9 111.0(2) . . ?
Cl8 C29 Cl7 110.8(2) . . ?
Cl9 C29 Cl7 109.6(2) . . ?
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
I1 C10 2.102(3) . ?
I2 C12 2.089(3) . ?
I3 C23 2.101(3) . ?
I4 C25 2.112(3) . ?
Ni1 O2 2.036(2) . ?
Ni1 O1 2.057(2) . ?
Ni1 N2 2.088(3) . ?
Ni1 N3 2.090(3) . ?
Ni1 N4 2.096(3) . ?
Ni1 N1 2.098(3) . ?
N1 C5 1.341(4) . ?
N1 C1 1.342(5) . ?
C1 C2 1.372(5) . ?
C2 C3 1.388(5) . ?
C3 C4 1.360(6) . ?
C4 C5 1.393(5) . ?
C5 C6 1.505(5) . ?
C6 N2 1.477(4) . ?
N2 C7 1.495(4) . ?
C7 C8 1.499(5) . ?
C8 C9 1.387(5) . ?
C8 C13 1.432(5) . ?
C9 C10 1.393(5) . ?
C10 C11 1.390(5) . ?
C11 C12 1.390(5) . ?
C12 C13 1.406(5) . ?
C13 O1 1.312(4) . ?
N3 C14 1.340(5) . ?
N3 C18 1.344(4) . ?
C14 C15 1.377(5) . ?
C15 C16 1.391(5) . ?
C16 C17 1.390(6) . ?
C17 C18 1.386(5) . ?
C18 C19 1.506(5) . ?
C19 N4 1.476(4) . ?
N4 C20 1.492(4) . ?
C20 C21 1.507(5) . ?
C21 C22 1.387(5) . ?
C21 C26 1.420(5) . ?
C22 C23 1.373(5) . ?
C23 C24 1.390(5) . ?
C24 C25 1.386(5) . ?
C25 C26 1.403(5) . ?
C26 O2 1.315(4) . ?
C27 Cl1 1.755(4) . ?
C27 Cl2 1.757(4) . ?
C27 Cl3 1.764(4) . ?
C28 Cl5 1.746(4) . ?
C28 Cl6 1.757(4) . ?
C28 Cl4 1.763(4) . ?
C29 Cl8 1.750(4) . ?
C29 Cl9 1.752(4) . ?
C29 Cl7 1.761(4) . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139126774
