#------------------------------------------------------------------------------
#$Date: 2025-08-18 16:30:32 +0300 (Mon, 18 Aug 2025) $
#$Revision: 301775 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/50/26/1502663.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_1502663
loop_
_publ_author_name
'Maldonado, Carmen R.'
'Marín, Clotilde'
'Olmo, Francisco'
'Huertas, Oscar'
'Quirós, Miguel'
'Sánchez-Moreno, Manuel'
'Rosales, María J'
'Salas, Juan M.'
_publ_section_title
;
 In vitro and in vivo trypanocidal evaluation of nickel complexes with an
 azapurine derivative against Trypanosoma cruzi.
;
_journal_issue                   19
_journal_name_full               'Journal of medicinal chemistry'
_journal_page_first              6964
_journal_page_last               6972
_journal_paper_doi               10.1021/jm100581z
_journal_volume                  53
_journal_year                    2010
_chemical_formula_moiety         'C36 H28 N14 Ni O4'
_chemical_formula_sum            'C36 H28 N14 Ni O4'
_chemical_formula_weight         779.43
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     heavy
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.107(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   13.226(3)
_cell_length_b                   15.714(3)
_cell_length_c                   16.609(3)
_cell_measurement_reflns_used    2553
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      19.9
_cell_measurement_theta_min      2.4
_cell_volume                     3451.9(12)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART (Bruker, 1999)'
_computing_data_reduction        'Bruker SAINT (Bruker, 1999)'
_computing_molecular_graphics    'Xtal_GX (Hall & du Boulay, 1997)'
_computing_publication_material  SHELXL-97
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      298(2)
_diffrn_detector_area_resol_mean 8.26
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.943
_diffrn_measurement_device_type  'Bruker SMART APEX CCD system'
_diffrn_measurement_method       'φ and ω scans'
_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  0.0591
_diffrn_reflns_av_sigmaI/netI    0.0707
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            20042
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         28.34
_diffrn_reflns_theta_min         2.01
_diffrn_standards_decay_%        -0.2
_diffrn_standards_number         83
_exptl_absorpt_coefficient_mu    0.626
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            pink
_exptl_crystal_density_diffrn    1.500
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       irregular
_exptl_crystal_F_000             1608
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.349
_refine_diff_density_min         -0.176
_refine_diff_density_rms         0.044
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.877
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     251
_refine_ls_number_reflns         4080
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.877
_refine_ls_R_factor_all          0.0877
_refine_ls_R_factor_gt           0.0435
_refine_ls_shift/su_max          0.008
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0400P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0911
_refine_ls_wR_factor_ref         0.1000
_reflns_number_gt                2270
_reflns_number_total             4080
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            jm100581z_si_003.cif
_cod_data_source_block           nif2ax
_cod_original_cell_volume        3451.8(11)
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               1502663
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'x, -y, z+1/2'
'x+1/2, y+1/2, z'
'x+1/2, -y+1/2, z+1/2'
'-x, -y, -z'
'-x, y, -z-1/2'
'-x+1/2, -y+1/2, -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
Ni Ni 0.5000 0.41691(3) 0.2500 0.04759(16) Uani 1 2 d S
N1 N 0.49788(15) 0.27694(13) 0.37759(12) 0.0584(6) Uani 1 1 d .
N2 N 0.44555(15) 0.32444(12) 0.32677(12) 0.0526(5) Uani 1 1 d .
N3 N 0.34502(15) 0.30546(13) 0.32647(12) 0.0548(5) Uani 1 1 d .
C3A C 0.33754(19) 0.24326(16) 0.38008(14) 0.0513(6) Uani 1 1 d .
N4 N 0.25017(16) 0.20102(14) 0.40129(13) 0.0600(6) Uani 1 1 d .
C4 C 0.15568(19) 0.21791(18) 0.35912(17) 0.0738(8) Uani 1 1 d .
H41 H 0.1378 0.1693 0.3271 0.089 Uiso 1 1 d R
H42 H 0.1637 0.2667 0.3249 0.089 Uiso 1 1 d R
H43 H 0.1032 0.2288 0.3976 0.089 Uiso 1 1 d R
C5 C 0.2545(3) 0.13752(19) 0.45828(16) 0.0665(8) Uani 1 1 d .
O5 O 0.17998(16) 0.09681(13) 0.47776(12) 0.0854(7) Uani 1 1 d .
N6 N 0.34969(19) 0.12200(14) 0.49317(13) 0.0671(6) Uani 1 1 d .
C6 C 0.3517(3) 0.05707(19) 0.55632(17) 0.0909(10) Uani 1 1 d .
H61 H 0.2863 0.0535 0.5812 0.109 Uiso 1 1 d R
H62 H 0.4013 0.0722 0.5961 0.109 Uiso 1 1 d R
H63 H 0.3688 0.0030 0.5331 0.109 Uiso 1 1 d R
C7 C 0.4422(2) 0.16085(18) 0.47305(16) 0.0643(8) Uani 1 1 d .
O7 O 0.51962(16) 0.14024(14) 0.50674(13) 0.0944(7) Uani 1 1 d .
C7A C 0.42985(19) 0.22447(16) 0.41266(15) 0.0525(6) Uani 1 1 d .
N1P N 0.44028(16) 0.51157(13) 0.32699(13) 0.0542(5) Uani 1 1 d .
C1AP C 0.3463(2) 0.53795(17) 0.30541(17) 0.0592(7) Uani 1 1 d .
C2P C 0.4808(2) 0.54571(18) 0.39117(18) 0.0691(8) Uani 1 1 d .
H2P H 0.5443 0.5266 0.4074 0.083 Uiso 1 1 d R
C3P C 0.4344(3) 0.6098(2) 0.43713(19) 0.0835(10) Uani 1 1 d .
H3P H 0.4660 0.6319 0.4826 0.100 Uiso 1 1 d R
C4P C 0.3419(3) 0.6386(2) 0.4140(2) 0.0907(11) Uani 1 1 d .
H4P H 0.3109 0.6822 0.4426 0.109 Uiso 1 1 d R
C4AP C 0.2932(3) 0.60245(19) 0.3471(2) 0.0783(9) Uani 1 1 d .
C5P C 0.1927(3) 0.6254(2) 0.3203(3) 0.1011(13) Uani 1 1 d .
H5P H 0.1577 0.6687 0.3464 0.121 Uiso 1 1 d R
C6P C 0.1501(3) 0.5850(3) 0.2584(3) 0.1042(14) Uani 1 1 d .
H6P H 0.0855 0.6012 0.2423 0.125 Uiso 1 1 d R
C6AP C 0.1998(2) 0.5173(2) 0.2159(2) 0.0800(10) Uani 1 1 d .
C7P C 0.1564(2) 0.4687(3) 0.1538(2) 0.0959(12) Uani 1 1 d .
H7P H 0.0904 0.4800 0.1374 0.115 Uiso 1 1 d R
C8P C 0.2099(2) 0.4056(2) 0.11760(19) 0.0853(10) Uani 1 1 d .
H8P H 0.1811 0.3734 0.0766 0.102 Uiso 1 1 d R
C9P C 0.3084(2) 0.39044(19) 0.14301(17) 0.0672(8) Uani 1 1 d .
H9P H 0.3445 0.3472 0.1178 0.081 Uiso 1 1 d R
N10P N 0.35334(15) 0.43336(13) 0.20069(13) 0.0552(6) Uani 1 1 d .
C0AP C 0.2996(2) 0.49586(18) 0.23850(17) 0.0608(7) 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'
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
N2 Ni N2 90.49(11) 6_656 .
N2 Ni N1P 178.40(8) 6_656 .
N2 Ni N1P 89.46(8) . .
N2 Ni N1P 89.45(8) 6_656 6_656
N2 Ni N1P 178.40(8) . 6_656
N1P Ni N1P 90.64(11) . 6_656
N2 Ni N10P 99.63(8) 6_656 .
N2 Ni N10P 90.26(8) . .
N1P Ni N10P 78.78(9) . .
N1P Ni N10P 91.32(8) 6_656 .
N2 Ni N10P 90.26(8) 6_656 6_656
N2 Ni N10P 99.63(8) . 6_656
N1P Ni N10P 91.32(8) . 6_656
N1P Ni N10P 78.78(9) 6_656 6_656
N10P Ni N10P 165.98(12) . 6_656
N2 N1 C7A 105.7(2) . .
N1 N2 N3 112.86(19) . .
N1 N2 Ni 127.55(16) . .
N3 N2 Ni 119.57(15) . .
C3A N3 N2 103.5(2) . .
N3 C3A C7A 110.9(2) . .
N3 C3A N4 126.1(2) . .
C7A C3A N4 122.9(2) . .
C5 N4 C3A 119.4(2) . .
C5 N4 C4 119.8(2) . .
C3A N4 C4 120.6(2) . .
N4 C4 H41 109.4 . .
N4 C4 H42 109.5 . .
H41 C4 H42 109.5 . .
N4 C4 H43 109.5 . .
H41 C4 H43 109.5 . .
H42 C4 H43 109.5 . .
O5 C5 N4 122.0(3) . .
O5 C5 N6 121.5(3) . .
N4 C5 N6 116.4(3) . .
C5 N6 C7 127.2(2) . .
C5 N6 C6 115.5(2) . .
C7 N6 C6 117.3(2) . .
N6 C6 H61 109.6 . .
N6 C6 H62 109.4 . .
H61 C6 H62 109.5 . .
N6 C6 H63 109.5 . .
H61 C6 H63 109.5 . .
H62 C6 H63 109.5 . .
O7 C7 N6 120.6(3) . .
O7 C7 C7A 127.5(3) . .
N6 C7 C7A 111.9(2) . .
N1 C7A C3A 107.0(2) . .
N1 C7A C7 130.9(2) . .
C3A C7A C7 122.1(3) . .
C2P N1P C1AP 117.6(2) . .
C2P N1P Ni 128.92(19) . .
C1AP N1P Ni 113.44(18) . .
N1P C1AP C4AP 123.0(3) . .
N1P C1AP C0AP 117.2(2) . .
C4AP C1AP C0AP 119.8(3) . .
N1P C2P C3P 123.9(3) . .
N1P C2P H2P 118.2 . .
C3P C2P H2P 118.0 . .
C4P C3P C2P 118.6(3) . .
C4P C3P H3P 120.6 . .
C2P C3P H3P 120.8 . .
C3P C4P C4AP 120.1(3) . .
C3P C4P H4P 119.9 . .
C4AP C4P H4P 120.0 . .
C4P C4AP C1AP 116.7(3) . .
C4P C4AP C5P 124.3(3) . .
C1AP C4AP C5P 119.0(3) . .
C6P C5P C4AP 120.4(4) . .
C6P C5P H5P 119.8 . .
C4AP C5P H5P 119.8 . .
C5P C6P C6AP 122.6(4) . .
C5P C6P H6P 118.6 . .
C6AP C6P H6P 118.8 . .
C7P C6AP C0AP 116.5(3) . .
C7P C6AP C6P 125.2(3) . .
C0AP C6AP C6P 118.3(3) . .
C8P C7P C6AP 120.5(3) . .
C8P C7P H7P 119.8 . .
C6AP C7P H7P 119.6 . .
C7P C8P C9P 118.7(3) . .
C7P C8P H8P 120.5 . .
C9P C8P H8P 120.8 . .
N10P C9P C8P 123.8(3) . .
N10P C9P H9P 118.1 . .
C8P C9P H9P 118.1 . .
C9P N10P C0AP 118.0(2) . .
C9P N10P Ni 129.17(19) . .
C0AP N10P Ni 112.75(18) . .
N10P C0AP C6AP 122.4(3) . .
N10P C0AP C1AP 117.7(2) . .
C6AP C0AP C1AP 119.8(3) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Ni N2 2.064(2) 6_656
Ni N2 2.064(2) .
Ni N1P 2.116(2) .
Ni N1P 2.116(2) 6_656
Ni N10P 2.120(2) .
Ni N10P 2.120(2) 6_656
N1 N2 1.322(2) .
N1 C7A 1.353(3) .
N2 N3 1.363(2) .
N3 C3A 1.326(3) .
C3A C7A 1.367(3) .
C3A N4 1.379(3) .
N4 C5 1.377(3) .
N4 C4 1.456(3) .
C4 H41 0.9601 .
C4 H42 0.9601 .
C4 H43 0.9601 .
C5 O5 1.219(3) .
C5 N6 1.406(3) .
N6 C7 1.408(3) .
N6 C6 1.463(3) .
C6 H61 0.9600 .
C6 H62 0.9601 .
C6 H63 0.9600 .
C7 O7 1.211(3) .
C7 C7A 1.425(3) .
N1P C2P 1.308(3) .
N1P C1AP 1.357(3) .
C1AP C4AP 1.415(4) .
C1AP C0AP 1.433(4) .
C2P C3P 1.406(4) .
C2P H2P 0.9300 .
C3P C4P 1.359(4) .
C3P H3P 0.9300 .
C4P C4AP 1.403(4) .
C4P H4P 0.9300 .
C4AP C5P 1.446(4) .
C5P C6P 1.332(5) .
C5P H5P 0.9300 .
C6P C6AP 1.438(5) .
C6P H6P 0.9300 .
C6AP C7P 1.405(4) .
C6AP C0AP 1.412(3) .
C7P C8P 1.359(4) .
C7P H7P 0.9300 .
C8P C9P 1.390(4) .
C8P H8P 0.9300 .
C9P N10P 1.313(3) .
C9P H9P 0.9300 .
N10P C0AP 1.366(3) .
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139037575
