#------------------------------------------------------------------------------
#$Date: 2025-08-21 13:21:36 +0200 (Thu 21 de Aug de 2025) $
#$Revision: 301847 $
#$URL: svn://www.crystallography.net/cod/cif/7/01/42/7014210.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_7014210
loop_
_publ_author_name
'Ye, Neng'
'Park, Gyungse'
'Przyborowska, Ann M.'
'Sloan, Paula E.'
'Clifford, Thomas'
'Bauer, Cary B.'
'Broker, Grant A.'
'Rogers, Robin D.'
'Ma, Rong'
'Torti, Suzy V.'
'Brechbiel, Martin W.'
'Planalp, Roy P.'
_publ_section_title
;
 Nickel(II), copper(II) and zinc(II) binding properties and
 cytotoxicity of tripodal, hexadentate tris(ethylenediamine)--analogue
 chelators.
;
_journal_issue                   9
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_page_first              1304
_journal_page_last               1311
_journal_paper_doi               10.1039/b403476g
_journal_year                    2004
_chemical_formula_structural     'RP31 (P286-005)'
_chemical_formula_sum            'C16 H40 Cl2 N6 Ni O9'
_chemical_formula_weight         590.15
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.4038(6)
_cell_length_b                   13.7359(9)
_cell_length_c                   20.1269(13)
_cell_measurement_reflns_used    4474
_cell_measurement_temperature    173(2)
_cell_volume                     2599.8(3)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_device       'Siemens P4'
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0683
_diffrn_reflns_av_sigmaI/netI    0.1014
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            16425
_diffrn_reflns_theta_full        27.92
_diffrn_reflns_theta_max         27.92
_diffrn_reflns_theta_min         2.02
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    1.007
_exptl_absorpt_correction_T_max  0.97
_exptl_absorpt_correction_T_min  0.71
_exptl_absorpt_correction_type   SADABS
_exptl_crystal_colour            'light purple'
_exptl_crystal_density_diffrn    1.508
_exptl_crystal_description       parallelepiped
_exptl_crystal_F_000             1248
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.421
_refine_diff_density_min         -0.433
_refine_diff_density_rms         0.077
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.022(17)
_refine_ls_extinction_coef       0.0011(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.017
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           fullcycle
_refine_ls_number_parameters     342
_refine_ls_number_reflns         6063
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.017
_refine_ls_R_factor_all          0.1064
_refine_ls_R_factor_gt           0.0561
_refine_ls_shift/su_max          0.440
_refine_ls_shift/su_mean         0.020
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0427P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0907
_refine_ls_wR_factor_ref         0.1048
_reflns_number_observed          4006
_reflns_number_total             6063
_reflns_observed_criterion       >2sigma(I)
_cod_data_source_file            b403476g.txt
_cod_data_source_block           rp31
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Orthorhombic' changed to 'orthorhombic'
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_original_sg_symbol_H-M      P2(1)2(1)2(1)
_cod_database_code               7014210
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -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
_atom_site_disorder_assembly
_atom_site_disorder_group
Ni Ni 0.36227(6) 0.02089(4) 0.35976(3) 0.02438(14) Uani 1 1 d . . .
Cl1 Cl 0.70812(13) -0.26367(8) 0.34496(5) 0.0344(3) Uani 1 1 d . . .
Cl2 Cl -0.30665(14) 0.24567(9) 0.42405(6) 0.0414(3) Uani 1 1 d . . .
O1 O 0.8141(4) -0.3195(3) 0.31133(19) 0.0639(11) Uani 1 1 d . A .
O2A O 0.6450(8) -0.2035(4) 0.2967(3) 0.107(3) Uani 0.75 1 d P A 1
O3A O 0.7622(6) -0.2067(5) 0.3976(3) 0.098(2) Uani 0.75 1 d P A 1
O4A O 0.5982(6) -0.3230(4) 0.3699(3) 0.094(2) Uani 0.75 1 d P A 1
O2B O 0.584(2) -0.2719(15) 0.3181(10) 0.114(7) Uiso 0.25 1 d P A 2
O3B O 0.749(2) -0.1705(16) 0.3440(11) 0.114(7) Uiso 0.25 1 d P A 2
O4B O 0.725(3) -0.2726(17) 0.4119(12) 0.128(8) Uiso 0.25 1 d P A 2
O5 O -0.4433(5) 0.2837(3) 0.4381(3) 0.1058(19) Uani 1 1 d . . .
O6 O -0.2901(5) 0.1596(3) 0.4613(2) 0.0937(16) Uani 1 1 d . . .
O7 O -0.2001(4) 0.3159(3) 0.44137(19) 0.0631(11) Uani 1 1 d . . .
O8 O -0.2963(5) 0.2209(3) 0.35692(19) 0.0880(15) Uani 1 1 d . . .
O9 O -0.4322(5) 0.4842(3) 0.48086(18) 0.0759(13) Uani 1 1 d . . .
H9O H -0.4234 0.4434 0.4457 0.091 Uiso 1 1 d R . .
N1 N 0.3243(3) -0.0119(2) 0.25855(16) 0.0307(9) Uani 1 1 d . . .
H1N H 0.2802 0.0425 0.2494 0.037 Uiso 1 1 d R . .
N2 N 0.3667(4) -0.1287(2) 0.38406(16) 0.0310(9) Uani 1 1 d . . .
H2N H 0.4333 -0.1574 0.3642 0.037 Uiso 1 1 d R . .
N3 N 0.1425(4) 0.0259(2) 0.37748(16) 0.0304(8) Uani 1 1 d . . .
H3N H 0.1304 0.0221 0.4265 0.037 Uiso 1 1 d R . .
N4 N 0.5770(3) 0.0236(3) 0.32629(15) 0.0290(8) Uani 1 1 d . . .
H4AN H 0.6454 0.0825 0.3368 0.035 Uiso 1 1 d R . .
H4BN H 0.5885 -0.0574 0.3185 0.035 Uiso 1 1 d R . .
N5 N 0.4249(4) 0.0349(2) 0.46093(15) 0.0280(9) Uani 1 1 d . . .
H5AN H 0.3579 0.0410 0.4919 0.034 Uiso 1 1 d R . .
H5BN H 0.4993 0.1021 0.4731 0.034 Uiso 1 1 d R . .
N6 N 0.3335(3) 0.1737(2) 0.34990(16) 0.0260(8) Uani 1 1 d . . .
H6AN H 0.3227 0.2025 0.3059 0.031 Uiso 1 1 d R . .
H6BN H 0.4105 0.2022 0.3627 0.031 Uiso 1 1 d R . .
C1 C 0.2191(5) -0.0914(3) 0.2471(2) 0.0393(12) Uani 1 1 d . . .
H1A H 0.2129 -0.1031 0.1981 0.047 Uiso 1 1 calc R . .
C2 C 0.2588(5) -0.1868(3) 0.2801(2) 0.0393(12) Uani 1 1 d . . .
H2A H 0.3577 -0.2034 0.2675 0.047 Uiso 1 1 calc R . .
H2B H 0.1963 -0.2387 0.2624 0.047 Uiso 1 1 calc R . .
C3 C 0.2480(5) -0.1871(3) 0.3563(3) 0.0392(11) Uani 1 1 d . . .
H3A H 0.2588 -0.2558 0.3721 0.047 Uiso 1 1 calc R . .
C4 C 0.1013(5) -0.1503(3) 0.3777(3) 0.0459(14) Uani 1 1 d . . .
H4B' H 0.0296 -0.2000 0.3657 0.055 Uiso 1 1 calc R . .
H4C H 0.1006 -0.1436 0.4267 0.055 Uiso 1 1 calc R . .
C5 C 0.0571(5) -0.0539(3) 0.3474(3) 0.0424(13) Uani 1 1 d . . .
H5B' H -0.0454 -0.0424 0.3580 0.051 Uiso 1 1 calc R . .
C6 C 0.0739(5) -0.0585(4) 0.2711(3) 0.0484(14) Uani 1 1 d . . .
H6B' H 0.0013 -0.1036 0.2531 0.058 Uiso 1 1 calc R . .
H6C H 0.0543 0.0069 0.2526 0.058 Uiso 1 1 calc R . .
C7 C 0.4612(5) -0.0241(3) 0.2238(2) 0.0365(11) Uani 1 1 d . . .
H7A H 0.4493 -0.0092 0.1760 0.044 Uiso 1 1 calc R . .
H7B H 0.4940 -0.0923 0.2279 0.044 Uiso 1 1 calc R . .
C8 C 0.5703(5) 0.0438(3) 0.2539(2) 0.0288(11) Uani 1 1 d . . .
H8A H 0.5359 0.1121 0.2478 0.035 Uiso 1 1 calc R . .
C9 C 0.7152(5) 0.0346(4) 0.2198(2) 0.0470(13) Uani 1 1 d . . .
H9A H 0.7826 0.0798 0.2405 0.070 Uiso 1 1 calc R . .
H9B H 0.7053 0.0504 0.1726 0.070 Uiso 1 1 calc R . .
H9C H 0.7502 -0.0322 0.2245 0.070 Uiso 1 1 calc R . .
C10 C 0.3865(6) -0.1391(3) 0.4567(2) 0.0385(12) Uani 1 1 d . . .
H10A H 0.4264 -0.2041 0.4668 0.046 Uiso 1 1 calc R . .
H10B H 0.2936 -0.1332 0.4794 0.046 Uiso 1 1 calc R . .
C11 C 0.4866(5) -0.0607(3) 0.4815(2) 0.0337(12) Uani 1 1 d . . .
H11A H 0.5803 -0.0690 0.4587 0.040 Uiso 1 1 calc R . .
C12 C 0.5106(6) -0.0681(4) 0.5559(2) 0.0500(15) Uani 1 1 d . . .
H12A H 0.5722 -0.0147 0.5705 0.075 Uiso 1 1 calc R . .
H12B H 0.5561 -0.1305 0.5662 0.075 Uiso 1 1 calc R . .
H12C H 0.4191 -0.0640 0.5790 0.075 Uiso 1 1 calc R . .
C13 C 0.0902(5) 0.1245(3) 0.3619(3) 0.0354(11) Uani 1 1 d . . .
H13A H -0.0003 0.1366 0.3857 0.043 Uiso 1 1 calc R . .
H13B H 0.0720 0.1302 0.3136 0.043 Uiso 1 1 calc R . .
C14 C 0.1986(5) 0.1981(3) 0.3826(2) 0.0301(11) Uani 1 1 d . . .
H14A H 0.2132 0.1907 0.4316 0.036 Uiso 1 1 calc R . .
C15 C 0.1508(5) 0.3023(3) 0.3700(2) 0.0430(12) Uani 1 1 d . . .
H15A H 0.2233 0.3475 0.3866 0.065 Uiso 1 1 calc R . .
H15B H 0.0608 0.3143 0.3932 0.065 Uiso 1 1 calc R . .
H15C H 0.1376 0.3124 0.3222 0.065 Uiso 1 1 calc R . .
C16 C -0.5727(7) 0.5238(5) 0.4743(3) 0.079(2) Uani 1 1 d . . .
H16A H -0.6419 0.4705 0.4720 0.119 Uiso 1 1 calc R . .
H16B H -0.5783 0.5628 0.4337 0.119 Uiso 1 1 calc R . .
H16C H -0.5939 0.5650 0.5128 0.119 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 0.0000 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'
Cl Cl 0.1484 0.1585 '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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N3 Ni N2 90.69(14) . . ?
N3 Ni N1 90.25(13) . . ?
N2 Ni N1 91.10(13) . . ?
N3 Ni N6 81.84(13) . . ?
N2 Ni N6 169.92(13) . . ?
N1 Ni N6 95.67(13) . . ?
N3 Ni N4 170.88(13) . . ?
N2 Ni N4 94.11(15) . . ?
N1 Ni N4 81.91(13) . . ?
N6 Ni N4 94.24(13) . . ?
N3 Ni N5 96.15(13) . . ?
N2 Ni N5 82.00(13) . . ?
N1 Ni N5 170.63(13) . . ?
N6 Ni N5 92.03(13) . . ?
N4 Ni N5 92.20(13) . . ?
O2B Cl1 O3B 109.7(13) . . ?
O2B Cl1 O4B 121.0(14) . . ?
O3B Cl1 O4B 93.8(13) . . ?
O2B Cl1 O2A 51.7(9) . . ?
O3B Cl1 O2A 63.2(9) . . ?
O4B Cl1 O2A 141.8(10) . . ?
O2B Cl1 O4A 55.7(9) . . ?
O3B Cl1 O4A 140.4(9) . . ?
O4B Cl1 O4A 71.5(10) . . ?
O2A Cl1 O4A 106.1(4) . . ?
O2B Cl1 O3A 133.6(9) . . ?
O3B Cl1 O3A 51.4(9) . . ?
O4B Cl1 O3A 42.7(10) . . ?
O2A Cl1 O3A 110.1(4) . . ?
O4A Cl1 O3A 108.5(4) . . ?
O2B Cl1 O1 112.6(9) . . ?
O3B Cl1 O1 107.9(9) . . ?
O4B Cl1 O1 109.7(10) . . ?
O2A Cl1 O1 106.4(3) . . ?
O4A Cl1 O1 111.7(3) . . ?
O3A Cl1 O1 113.7(3) . . ?
O8 Cl2 O6 107.6(3) . . ?
O8 Cl2 O5 110.3(3) . . ?
O6 Cl2 O5 107.7(3) . . ?
O8 Cl2 O7 110.5(2) . . ?
O6 Cl2 O7 111.0(3) . . ?
O5 Cl2 O7 109.7(3) . . ?
C7 N1 C1 115.0(3) . . ?
C7 N1 Ni 109.5(2) . . ?
C1 N1 Ni 114.7(3) . . ?
C10 N2 C3 114.5(4) . . ?
C10 N2 Ni 108.9(2) . . ?
C3 N2 Ni 115.1(3) . . ?
C13 N3 C5 114.2(4) . . ?
C13 N3 Ni 108.8(2) . . ?
C5 N3 Ni 116.0(3) . . ?
C8 N4 Ni 105.9(2) . . ?
C11 N5 Ni 107.1(3) . . ?
C14 N6 Ni 107.1(2) . . ?
N1 C1 C2 113.7(4) . . ?
N1 C1 C6 109.2(4) . . ?
C2 C1 C6 109.8(4) . . ?
C1 C2 C3 115.1(4) . . ?
N2 C3 C4 113.1(4) . . ?
N2 C3 C2 108.9(4) . . ?
C4 C3 C2 109.9(4) . . ?
C5 C4 C3 115.0(4) . . ?
N3 C5 C4 109.4(4) . . ?
N3 C5 C6 112.3(4) . . ?
C4 C5 C6 109.6(4) . . ?
C1 C6 C5 114.9(4) . . ?
N1 C7 C8 109.4(3) . . ?
N4 C8 C7 107.9(3) . . ?
N4 C8 C9 112.8(3) . . ?
C7 C8 C9 111.9(4) . . ?
N2 C10 C11 109.6(4) . . ?
N5 C11 C10 107.0(4) . . ?
N5 C11 C12 113.0(4) . . ?
C10 C11 C12 111.7(4) . . ?
N3 C13 C14 109.5(4) . . ?
N6 C14 C13 108.1(3) . . ?
N6 C14 C15 113.3(4) . . ?
C13 C14 C15 112.8(4) . . ?
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
Ni N3 2.098(4) . ?
Ni N2 2.113(3) . ?
Ni N1 2.117(3) . ?
Ni N6 2.125(3) . ?
Ni N4 2.129(3) . ?
Ni N5 2.129(3) . ?
Cl1 O2B 1.29(2) . ?
Cl1 O3B 1.34(2) . ?
Cl1 O4B 1.36(2) . ?
Cl1 O2A 1.407(4) . ?
Cl1 O4A 1.409(5) . ?
Cl1 O3A 1.411(5) . ?
Cl1 O1 1.428(3) . ?
Cl2 O8 1.397(4) . ?
Cl2 O6 1.408(4) . ?
Cl2 O5 1.416(4) . ?
Cl2 O7 1.434(4) . ?
O9 C16 1.435(7) . ?
N1 C7 1.475(5) . ?
N1 C1 1.491(5) . ?
N2 C10 1.480(5) . ?
N2 C3 1.484(5) . ?
N3 C13 1.475(5) . ?
N3 C5 1.488(5) . ?
N4 C8 1.484(5) . ?
N5 C11 1.494(5) . ?
N6 C14 1.468(5) . ?
C1 C2 1.516(6) . ?
C1 C6 1.518(6) . ?
C2 C3 1.536(7) . ?
C3 C4 1.531(6) . ?
C4 C5 1.516(6) . ?
C5 C6 1.545(7) . ?
C7 C8 1.513(6) . ?
C8 C9 1.531(6) . ?
C10 C11 1.515(6) . ?
C11 C12 1.518(6) . ?
C13 C14 1.494(6) . ?
C14 C15 1.522(5) . ?
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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C1 C2 C3 C4 51.7(5) . . . . ?
C2 C3 C4 C5 -51.6(5) . . . . ?
C3 C4 C5 C6 51.8(5) . . . . ?
C4 C5 C6 C1 -52.5(5) . . . . ?
C5 C6 C1 C2 52.6(5) . . . . ?
C6 C1 C2 C3 -52.3(5) . . . . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139155721
