#------------------------------------------------------------------------------
#$Date: 2025-08-21 00:01:10 +0200 (Thu 21 de Aug de 2025) $
#$Revision: 301838 $
#$URL: svn://www.crystallography.net/cod/cif/4/32/91/4329163.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_4329163
loop_
_publ_author_name
'Sellamuthu Anbu'
'Subban Kamalraj'
'Babu Varghese'
'Johnpaul Muthumary'
'Muthusamy Kandaswamy'
_publ_contact_author_address
;Department of Inorganic Chemistry
School of Chemical Sceinces
University of Madras
Guindy Campus
chennai - 600 025
India.
;
_publ_contact_author_email       mkands@yahoo.com
_publ_contact_author_fax         +91(44)22300488
_publ_contact_author_name        'Professor M. Kandaswamy'
_publ_contact_author_phone       +91(44)22300488
_publ_section_title
;
 A Series of Oxyimine-Based Macrocyclic Dinuclear Zinc(II) Complexes
 Enhances Phosphate Ester Hydrolysis, DNA Binding, DNA Hydrolysis, and
 Lactate Dehydrogenase Inhibition and Induces Apoptosis
;
_journal_name_full               'Inorganic Chemistry'
_journal_page_first              5580
_journal_page_last               5592
_journal_paper_doi               10.1021/ic202451e
_journal_volume                  51
_journal_year                    2012
_chemical_formula_moiety         'C22 H24 N4 O6'
_chemical_formula_sum            'C22 H24 N4 O6'
_chemical_formula_weight         440.45
_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_method           SHELXL-97
_cell_angle_alpha                99.9960(10)
_cell_angle_beta                 94.2960(10)
_cell_angle_gamma                101.0840(10)
_cell_formula_units_Z            2
_cell_length_a                   8.0437(4)
_cell_length_b                   11.2976(5)
_cell_length_c                   12.0851(5)
_cell_measurement_temperature    293(2)
_cell_volume                     1054.70(8)
_computing_cell_refinement       'APEX2/SAINT (Bruker, 2004)'
_computing_data_collection       'APEX2 (Bruker, 2004)'
_computing_data_reduction        'SAINT/XPREP (Bruker, 2004)'
_computing_molecular_graphics
'ORTEP3 (Farrugia, 1997) and Mercury (Bruno et al., 2002)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SIR92 (Altornare et al., 1993)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'bruker axs kappa apex2 CCD Diffractometer'
_diffrn_measurement_method       'ω and φ scan'
_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  0.0245
_diffrn_reflns_av_sigmaI/netI    0.0187
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            23422
_diffrn_reflns_theta_full        28.27
_diffrn_reflns_theta_max         28.27
_diffrn_reflns_theta_min         1.72
_exptl_absorpt_coefficient_mu    0.103
_exptl_absorpt_correction_T_max  0.985
_exptl_absorpt_correction_T_min  0.982
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Bruker 1999)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.387
_exptl_crystal_description       prism
_exptl_crystal_F_000             464
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.254
_refine_diff_density_min         -0.181
_refine_diff_density_rms         0.037
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.990
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     291
_refine_ls_number_reflns         5199
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.990
_refine_ls_R_factor_all          0.0560
_refine_ls_R_factor_gt           0.0412
_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)+(0.0819P)²+0.1846P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1219
_refine_ls_wR_factor_ref         0.1391
_reflns_number_gt                4014
_reflns_number_total             5199
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ic202451e_si_002.cif
_cod_data_source_block           fin
_cod_depositor_comments
;

2021-04-14
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_moiety     'C44 H48 N8 O12'
_cod_original_formula_sum        'C44 H48 N8 O12'
_cod_original_formula_units_Z    1
_cod_original_formula_weight     880.90
_cod_database_code               4329163
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
C22 C 0.0740(2) 0.45148(13) 0.69449(14) 0.0570(4) Uani 1 1 d .
H22A H 0.1501 0.4207 0.6434 0.068 Uiso 1 1 calc R
H22B H 0.1221 0.5376 0.7249 0.068 Uiso 1 1 calc R
O1 O 0.39773(14) 0.02994(10) 0.88633(9) 0.0510(3) Uani 1 1 d .
H1 H 0.4240 0.1015 0.8783 0.077 Uiso 1 1 calc R
C1 C 0.44539(16) -0.04413(13) 0.79991(11) 0.0394(3) Uani 1 1 d .
C6 C 0.52684(17) 0.00112(13) 0.71203(11) 0.0404(3) Uani 1 1 d .
O2 O 0.22359(14) -0.33877(10) 1.00053(9) 0.0522(3) Uani 1 1 d .
C2 C 0.41138(16) -0.16992(13) 0.79953(11) 0.0402(3) Uani 1 1 d .
O3 O 0.58187(17) 0.33021(10) 0.77699(9) 0.0607(3) Uani 1 1 d .
N2 N 0.32671(16) -0.31803(12) 0.91335(10) 0.0476(3) Uani 1 1 d .
C5 C 0.57292(17) -0.08203(14) 0.62643(11) 0.0436(3) Uani 1 1 d .
H5 H 0.6276 -0.0522 0.5687 0.052 Uiso 1 1 calc R
C3 C 0.45893(17) -0.24939(13) 0.71149(11) 0.0430(3) Uani 1 1 d .
H3 H 0.4353 -0.3333 0.7112 0.052 Uiso 1 1 calc R
C4 C 0.54048(17) -0.20696(14) 0.62418(11) 0.0437(3) Uani 1 1 d .
N1 N 0.53455(17) 0.20902(11) 0.79163(11) 0.0496(3) Uani 1 1 d .
C9 C 0.32512(17) -0.21302(13) 0.89149(11) 0.0436(3) Uani 1 1 d .
H9 H 0.2674 -0.1617 0.9352 0.052 Uiso 1 1 calc R
C8 C 0.56902(18) 0.13186(14) 0.71165(12) 0.0457(3) Uani 1 1 d .
H8 H 0.6218 0.1594 0.6522 0.055 Uiso 1 1 calc R
C11 C 0.2584(2) -0.44149(14) 1.04422(13) 0.0540(4) Uani 1 1 d .
H11A H 0.2619 -0.5073 0.9817 0.065 Uiso 1 1 calc R
H11B H 0.1663 -0.4706 1.0866 0.065 Uiso 1 1 calc R
C7 C 0.5914(2) -0.29488(16) 0.53063(13) 0.0564(4) Uani 1 1 d .
H7A H 0.5588 -0.3773 0.5435 0.085 Uiso 1 1 calc R
H7B H 0.7126 -0.2745 0.5293 0.085 Uiso 1 1 calc R
H7C H 0.5351 -0.2890 0.4595 0.085 Uiso 1 1 calc R
C10 C 0.5770(2) 0.41240(15) 0.88071(14) 0.0567(4) Uani 1 1 d .
H10A H 0.4863 0.3756 0.9205 0.068 Uiso 1 1 calc R
H10B H 0.5510 0.4881 0.8637 0.068 Uiso 1 1 calc R
O4 O 0.13670(14) 0.07208(9) 0.61336(8) 0.0488(3) Uani 1 1 d .
H4 H 0.1394 0.1452 0.6363 0.073 Uiso 1 1 calc R
C13 C 0.05772(16) 0.00565(12) 0.68389(11) 0.0381(3) Uani 1 1 d .
C15 C -0.08801(18) -0.01540(14) 0.84919(11) 0.0436(3) Uani 1 1 d .
H15 H -0.1331 0.0205 0.9121 0.052 Uiso 1 1 calc R
C12 C 0.04290(16) -0.12157(12) 0.65977(11) 0.0382(3) Uani 1 1 d .
O6 O 0.16645(13) -0.31787(9) 0.42845(8) 0.0488(3) Uani 1 1 d .
C14 C -0.01039(17) 0.05952(13) 0.77938(11) 0.0398(3) Uani 1 1 d .
C17 C -0.03447(17) -0.19210(13) 0.73262(11) 0.0419(3) Uani 1 1 d .
H17 H -0.0424 -0.2767 0.7167 0.050 Uiso 1 1 calc R
O5 O 0.06287(17) 0.38498(10) 0.78527(9) 0.0600(3) Uani 1 1 d .
N3 N 0.06657(17) 0.26168(11) 0.74397(11) 0.0501(3) Uani 1 1 d .
C20 C 0.11218(17) -0.17549(12) 0.55967(11) 0.0409(3) Uani 1 1 d .
H20 H 0.1845 -0.1246 0.5229 0.049 Uiso 1 1 calc R
N4 N 0.07626(16) -0.28987(11) 0.52164(10) 0.0455(3) Uani 1 1 d .
C21 C 0.0960(2) -0.43989(13) 0.36974(12) 0.0512(4) Uani 1 1 d .
H21A H 0.0846 -0.4944 0.4237 0.061 Uiso 1 1 calc R
H21B H 0.1738 -0.4659 0.3176 0.061 Uiso 1 1 calc R
C18 C -0.00374(19) 0.19099(13) 0.80591(11) 0.0456(3) Uani 1 1 d .
H18 H -0.0515 0.2237 0.8689 0.055 Uiso 1 1 calc R
C16 C -0.10034(18) -0.14108(14) 0.82821(11) 0.0434(3) Uani 1 1 d .
C19 C -0.1818(2) -0.22066(16) 0.90524(13) 0.0562(4) Uani 1 1 d .
H19A H -0.2198 -0.1704 0.9667 0.084 Uiso 1 1 calc R
H19B H -0.1002 -0.2624 0.9346 0.084 Uiso 1 1 calc R
H19C H -0.2776 -0.2800 0.8637 0.084 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'
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
O5 C22 C21 111.99(13) . 2_556
O5 C22 H22A 109.2 . .
C21 C22 H22A 109.2 2_556 .
O5 C22 H22B 109.2 . .
C21 C22 H22B 109.2 2_556 .
H22A C22 H22B 107.9 . .
C1 O1 H1 109.5 . .
O1 C1 C2 117.59(12) . .
O1 C1 C6 122.51(13) . .
C2 C1 C6 119.89(12) . .
C5 C6 C1 118.67(13) . .
C5 C6 C8 119.95(12) . .
C1 C6 C8 121.33(13) . .
N2 O2 C11 109.44(10) . .
C1 C2 C3 119.21(12) . .
C1 C2 C9 118.11(12) . .
C3 C2 C9 122.67(13) . .
N1 O3 C10 109.64(11) . .
C9 N2 O2 109.69(11) . .
C4 C5 C6 122.49(13) . .
C4 C5 H5 118.8 . .
C6 C5 H5 118.8 . .
C4 C3 C2 122.01(13) . .
C4 C3 H3 119.0 . .
C2 C3 H3 119.0 . .
C5 C4 C3 117.73(12) . .
C5 C4 C7 121.44(13) . .
C3 C4 C7 120.83(14) . .
C8 N1 O3 113.02(12) . .
N2 C9 C2 121.79(13) . .
N2 C9 H9 119.1 . .
C2 C9 H9 119.1 . .
N1 C8 C6 120.65(13) . .
N1 C8 H8 119.7 . .
C6 C8 H8 119.7 . .
O2 C11 C10 112.93(13) . 2_657
O2 C11 H11A 109.0 . .
C10 C11 H11A 109.0 2_657 .
O2 C11 H11B 109.0 . .
C10 C11 H11B 109.0 2_657 .
H11A C11 H11B 107.8 . .
C4 C7 H7A 109.5 . .
C4 C7 H7B 109.5 . .
H7A C7 H7B 109.5 . .
C4 C7 H7C 109.5 . .
H7A C7 H7C 109.5 . .
H7B C7 H7C 109.5 . .
O3 C10 C11 112.43(14) . 2_657
O3 C10 H10A 109.1 . .
C11 C10 H10A 109.1 2_657 .
O3 C10 H10B 109.1 . .
C11 C10 H10B 109.1 2_657 .
H10A C10 H10B 107.8 . .
C13 O4 H4 109.5 . .
O4 C13 C12 117.97(11) . .
O4 C13 C14 122.57(12) . .
C12 C13 C14 119.46(12) . .
C16 C15 C14 122.30(12) . .
C16 C15 H15 118.8 . .
C14 C15 H15 118.8 . .
C17 C12 C13 119.18(12) . .
C17 C12 C20 122.29(12) . .
C13 C12 C20 118.52(12) . .
N4 O6 C21 109.35(10) . .
C15 C14 C13 119.08(12) . .
C15 C14 C18 119.32(12) . .
C13 C14 C18 121.59(13) . .
C16 C17 C12 122.48(13) . .
C16 C17 H17 118.8 . .
C12 C17 H17 118.8 . .
N3 O5 C22 109.52(11) . .
C18 N3 O5 111.87(12) . .
N4 C20 C12 121.46(13) . .
N4 C20 H20 119.3 . .
C12 C20 H20 119.3 . .
C20 N4 O6 109.80(11) . .
O6 C21 C22 112.79(12) . 2_556
O6 C21 H21A 109.0 . .
C22 C21 H21A 109.0 2_556 .
O6 C21 H21B 109.0 . .
C22 C21 H21B 109.0 2_556 .
H21A C21 H21B 107.8 . .
N3 C18 C14 120.75(13) . .
N3 C18 H18 119.6 . .
C14 C18 H18 119.6 . .
C15 C16 C17 117.46(13) . .
C15 C16 C19 121.79(13) . .
C17 C16 C19 120.75(14) . .
C16 C19 H19A 109.5 . .
C16 C19 H19B 109.5 . .
H19A C19 H19B 109.5 . .
C16 C19 H19C 109.5 . .
H19A C19 H19C 109.5 . .
H19B C19 H19C 109.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C22 O5 1.432(2) .
C22 C21 1.492(2) 2_556
C22 H22A 0.9700 .
C22 H22B 0.9700 .
O1 C1 1.3483(16) .
O1 H1 0.8200 .
C1 C2 1.3937(19) .
C1 C6 1.4081(18) .
C6 C5 1.3943(19) .
C6 C8 1.451(2) .
O2 N2 1.4123(14) .
O2 C11 1.4211(18) .
C2 C3 1.3950(18) .
C2 C9 1.4585(19) .
O3 N1 1.3944(16) .
O3 C10 1.4326(18) .
N2 C9 1.2616(19) .
C5 C4 1.380(2) .
C5 H5 0.9300 .
C3 C4 1.3900(19) .
C3 H3 0.9300 .
C4 C7 1.5059(19) .
N1 C8 1.2695(19) .
C9 H9 0.9300 .
C8 H8 0.9300 .
C11 C10 1.495(2) 2_657
C11 H11A 0.9700 .
C11 H11B 0.9700 .
C7 H7A 0.9600 .
C7 H7B 0.9600 .
C7 H7C 0.9600 .
C10 C11 1.495(2) 2_657
C10 H10A 0.9700 .
C10 H10B 0.9700 .
O4 C13 1.3467(16) .
O4 H4 0.8200 .
C13 C12 1.3958(18) .
C13 C14 1.4076(18) .
C15 C16 1.381(2) .
C15 C14 1.393(2) .
C15 H15 0.9300 .
C12 C17 1.3902(19) .
C12 C20 1.4562(17) .
O6 N4 1.4078(14) .
O6 C21 1.4229(17) .
C14 C18 1.4538(19) .
C17 C16 1.3876(19) .
C17 H17 0.9300 .
O5 N3 1.4025(15) .
N3 C18 1.271(2) .
C20 N4 1.2629(17) .
C20 H20 0.9300 .
C21 C22 1.492(2) 2_556
C21 H21A 0.9700 .
C21 H21B 0.9700 .
C18 H18 0.9300 .
C16 C19 1.503(2) .
C19 H19A 0.9600 .
C19 H19B 0.9600 .
C19 H19C 0.9600 .
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139137288
