#------------------------------------------------------------------------------
#$Date: 2025-08-18 17:33:07 +0200 (Mon 18 de Aug de 2025) $
#$Revision: 301779 $
#$URL: svn://www.crystallography.net/cod/cif/1/54/40/1544022.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_1544022
loop_
_publ_author_name
'Wang Jing-lin'
'Zhao Ya-qin'
'Yang Bin-sheng'
_publ_section_title
;
 Transition metal complexes of asymmetrical aroyl-hydrazone ligand:
 Syntheses, structures, DNA binding and cleavage studies
;
_journal_name_full               'Inorganica Chimica Acta'
_journal_page_first              484
_journal_page_last               496
_journal_paper_doi               10.1016/j.ica.2013.09.001
_journal_volume                  409B
_journal_year                    2014
_chemical_formula_sum            'C14 H13 N4 O6 V'
_chemical_formula_weight         384.22
_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
_cell_angle_alpha                89.029(2)
_cell_angle_beta                 70.6470(10)
_cell_angle_gamma                63.2440(10)
_cell_formula_units_Z            2
_cell_length_a                   9.4462(12)
_cell_length_b                   9.9937(14)
_cell_length_c                   10.0415(16)
_cell_measurement_reflns_used    2157
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      27.664
_cell_measurement_theta_min      2.177
_cell_volume                     788.7(2)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.983
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega 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  0.0125
_diffrn_reflns_av_sigmaI/netI    0.0278
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            4122
_diffrn_reflns_theta_full        25.04
_diffrn_reflns_theta_max         25.04
_diffrn_reflns_theta_min         2.18
_exptl_absorpt_coefficient_mu    0.670
_exptl_absorpt_correction_T_max  0.8557
_exptl_absorpt_correction_T_min  0.7661
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.618
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             392
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.39
_exptl_crystal_size_min          0.24
_refine_diff_density_max         0.364
_refine_diff_density_min         -0.317
_refine_diff_density_rms         0.069
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.081
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     228
_refine_ls_number_reflns         2742
_refine_ls_number_restraints     12
_refine_ls_restrained_S_all      1.094
_refine_ls_R_factor_all          0.0480
_refine_ls_R_factor_gt           0.0361
_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)+(0.0423P)²+0.4436P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0872
_refine_ls_wR_factor_ref         0.0967
_reflns_number_gt                2238
_reflns_number_total             2742
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ICA-2014-409B-484-496-6.cif
_cod_data_source_block           090622b
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to the built-in table from CIF Core dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 4624 2016-04-14 12:54:50Z antanas 

The following automatic conversions were performed:

'_journal_paper_doi' value
'http://dx.doi.org/10.1016/j.ica.2013.09.001' was changed to
'10.1016/j.ica.2013.09.001'.

Automatic conversion script
Id: cif_fix_values 6433 2018-09-21 13:16:33Z andrius 
;
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               1544022
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
_atom_site_disorder_assembly
_atom_site_disorder_group
V1 V 0.59191(5) 0.19972(5) 0.45440(5) 0.03593(16) Uani 1 1 d . . .
N1 N 0.3750(3) 0.4933(2) 0.3772(2) 0.0373(5) Uani 1 1 d . . .
N2 N 0.5412(2) 0.3737(2) 0.3307(2) 0.0331(5) Uani 1 1 d . . .
N3 N 0.0028(3) 0.6926(2) 0.5286(2) 0.0343(5) Uani 1 1 d . . .
N4 N -0.2993(3) 0.6907(3) 0.8531(3) 0.0499(6) Uani 1 1 d . . .
O1 O 0.3629(2) 0.3541(2) 0.56000(19) 0.0401(4) Uani 1 1 d . . .
O2 O -0.2871(3) 0.5951(3) 0.9318(3) 0.0825(8) Uani 1 1 d U . .
O3 O -0.4305(3) 0.8075(3) 0.8741(3) 0.0751(8) Uani 1 1 d U . .
O4 O 0.8127(2) 0.1619(2) 0.36497(19) 0.0402(4) Uani 1 1 d . . .
O5 O 0.6043(2) 0.1331(2) 0.6148(2) 0.0539(6) Uani 1 1 d . . .
O6 O 0.5756(3) 0.0832(2) 0.3645(2) 0.0535(5) Uani 1 1 d . . .
C1 C 0.2904(3) 0.4696(3) 0.4983(3) 0.0327(6) Uani 1 1 d . . .
C2 C 0.1092(3) 0.5665(3) 0.5738(3) 0.0315(5) Uani 1 1 d . . .
C3 C 0.0115(3) 0.5479(3) 0.7005(3) 0.0354(6) Uani 1 1 d . . .
H3 H 0.0483 0.4728 0.7553 0.043 Uiso 1 1 calc R . .
C4 C -0.1540(3) 0.6636(3) 0.7311(3) 0.0364(6) Uani 1 1 d . . .
C5 C -0.1558(3) 0.7514(3) 0.6245(3) 0.0374(6) Uani 1 1 d . . .
H5 H -0.2503 0.8364 0.6198 0.045 Uiso 1 1 calc R . .
C6 C 0.0508(4) 0.7582(3) 0.3999(3) 0.0457(7) Uani 1 1 d . . .
H6A H -0.0494 0.8404 0.3925 0.069 Uiso 1 1 calc R . .
H6B H 0.1067 0.6818 0.3171 0.069 Uiso 1 1 calc R . .
H6C H 0.1265 0.7954 0.4061 0.069 Uiso 1 1 calc R . .
C7 C 0.6440(3) 0.3759(3) 0.2091(3) 0.0377(6) Uani 1 1 d . . .
H7 H 0.6014 0.4534 0.1582 0.045 Uiso 1 1 calc R . .
C8 C 0.8198(3) 0.2658(3) 0.1483(3) 0.0369(6) Uani 1 1 d . . .
C9 C 0.8991(3) 0.1617(3) 0.2284(3) 0.0359(6) Uani 1 1 d . . .
C10 C 1.0720(3) 0.0598(3) 0.1675(3) 0.0477(7) Uani 1 1 d . . .
H10 H 1.1258 -0.0089 0.2205 0.057 Uiso 1 1 calc R . .
C11 C 1.1633(4) 0.0611(3) 0.0285(3) 0.0533(8) Uani 1 1 d . . .
H11 H 1.2782 -0.0086 -0.0121 0.064 Uiso 1 1 calc R . .
C12 C 1.0872(4) 0.1636(4) -0.0511(3) 0.0542(8) Uani 1 1 d . . .
H12 H 1.1507 0.1637 -0.1444 0.065 Uiso 1 1 calc R . .
C13 C 0.9172(4) 0.2657(3) 0.0080(3) 0.0490(7) Uani 1 1 d . . .
H13 H 0.8661 0.3355 -0.0455 0.059 Uiso 1 1 calc R . .
C14 C 0.5222(4) 0.1826(4) 0.7614(3) 0.0595(9) Uani 1 1 d . . .
H14A H 0.5738 0.2328 0.7933 0.089 Uiso 1 1 calc R . .
H14B H 0.5318 0.0972 0.8100 0.089 Uiso 1 1 calc R . .
H14C H 0.4042 0.2521 0.7821 0.089 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'
O O 0.0106 0.0060 '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'
V V 0.3005 0.5294 '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
O6 V1 O5 107.93(11) . .
O6 V1 O4 103.85(10) . .
O5 V1 O4 99.28(9) . .
O6 V1 O1 106.17(10) . .
O5 V1 O1 88.75(8) . .
O4 V1 O1 144.73(8) . .
O6 V1 N2 98.64(10) . .
O5 V1 N2 151.64(10) . .
O4 V1 N2 83.41(8) . .
O1 V1 N2 74.20(8) . .
C1 N1 N2 107.4(2) . .
C7 N2 N1 116.3(2) . .
C7 N2 V1 126.46(17) . .
N1 N2 V1 116.95(15) . .
C5 N3 C2 109.2(2) . .
C5 N3 C6 123.3(2) . .
C2 N3 C6 127.5(2) . .
O3 N4 O2 122.8(3) . .
O3 N4 C4 118.7(3) . .
O2 N4 C4 118.5(2) . .
C1 O1 V1 118.60(15) . .
C9 O4 V1 130.91(17) . .
C14 O5 V1 139.32(19) . .
N1 C1 O1 122.0(2) . .
N1 C1 C2 122.7(2) . .
O1 C1 C2 115.2(2) . .
C3 C2 N3 107.7(2) . .
C3 C2 C1 126.0(2) . .
N3 C2 C1 126.3(2) . .
C2 C3 C4 106.5(2) . .
C2 C3 H3 126.8 . .
C4 C3 H3 126.8 . .
C5 C4 C3 109.0(2) . .
C5 C4 N4 124.4(2) . .
C3 C4 N4 126.6(3) . .
N3 C5 C4 107.7(2) . .
N3 C5 H5 126.2 . .
C4 C5 H5 126.2 . .
N3 C6 H6A 109.5 . .
N3 C6 H6B 109.5 . .
H6A C6 H6B 109.5 . .
N3 C6 H6C 109.5 . .
H6A C6 H6C 109.5 . .
H6B C6 H6C 109.5 . .
N2 C7 C8 123.6(2) . .
N2 C7 H7 118.2 . .
C8 C7 H7 118.2 . .
C9 C8 C13 119.0(2) . .
C9 C8 C7 121.2(2) . .
C13 C8 C7 119.8(3) . .
O4 C9 C10 119.2(3) . .
O4 C9 C8 121.1(2) . .
C10 C9 C8 119.7(3) . .
C11 C10 C9 119.8(3) . .
C11 C10 H10 120.1 . .
C9 C10 H10 120.1 . .
C12 C11 C10 121.2(3) . .
C12 C11 H11 119.4 . .
C10 C11 H11 119.4 . .
C13 C12 C11 119.6(3) . .
C13 C12 H12 120.2 . .
C11 C12 H12 120.2 . .
C12 C13 C8 120.7(3) . .
C12 C13 H13 119.6 . .
C8 C13 H13 119.6 . .
O5 C14 H14A 109.5 . .
O5 C14 H14B 109.5 . .
H14A C14 H14B 109.5 . .
O5 C14 H14C 109.5 . .
H14A C14 H14C 109.5 . .
H14B C14 H14C 109.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
V1 O6 1.576(2) .
V1 O5 1.752(2) .
V1 O4 1.8325(17) .
V1 O1 1.9272(17) .
V1 N2 2.090(2) .
N1 C1 1.300(3) .
N1 N2 1.398(3) .
N2 C7 1.291(3) .
N3 C5 1.337(3) .
N3 C2 1.395(3) .
N3 C6 1.468(3) .
N4 O3 1.215(3) .
N4 O2 1.220(3) .
N4 C4 1.421(3) .
O1 C1 1.316(3) .
O4 C9 1.343(3) .
O5 C14 1.392(3) .
C1 C2 1.454(3) .
C2 C3 1.369(4) .
C3 C4 1.394(3) .
C3 H3 0.9300 .
C4 C5 1.372(4) .
C5 H5 0.9300 .
C6 H6A 0.9600 .
C6 H6B 0.9600 .
C6 H6C 0.9600 .
C7 C8 1.431(3) .
C7 H7 0.9300 .
C8 C9 1.399(4) .
C8 C13 1.405(4) .
C9 C10 1.393(4) .
C10 C11 1.380(4) .
C10 H10 0.9300 .
C11 C12 1.376(4) .
C11 H11 0.9300 .
C12 C13 1.373(4) .
C12 H12 0.9300 .
C13 H13 0.9300 .
C14 H14A 0.9600 .
C14 H14B 0.9600 .
C14 H14C 0.9600 .
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
C1 N1 N2 C7 178.4(2) . . . .
C1 N1 N2 V1 4.0(3) . . . .
O6 V1 N2 C7 -75.9(2) . . . .
O5 V1 N2 C7 124.5(2) . . . .
O4 V1 N2 C7 27.2(2) . . . .
O1 V1 N2 C7 179.6(2) . . . .
O6 V1 N2 N1 97.82(18) . . . .
O5 V1 N2 N1 -61.8(3) . . . .
O4 V1 N2 N1 -159.11(18) . . . .
O1 V1 N2 N1 -6.64(16) . . . .
O6 V1 O1 C1 -86.5(2) . . . .
O5 V1 O1 C1 165.17(19) . . . .
O4 V1 O1 C1 60.8(2) . . . .
N2 V1 O1 C1 8.11(18) . . . .
O6 V1 O4 C9 55.8(2) . . . .
O5 V1 O4 C9 167.0(2) . . . .
O1 V1 O4 C9 -91.8(2) . . . .
N2 V1 O4 C9 -41.5(2) . . . .
O6 V1 O5 C14 -125.1(3) . . . .
O4 V1 O5 C14 127.0(3) . . . .
O1 V1 O5 C14 -18.5(3) . . . .
N2 V1 O5 C14 33.7(4) . . . .
N2 N1 C1 O1 3.0(3) . . . .
N2 N1 C1 C2 -175.8(2) . . . .
V1 O1 C1 N1 -9.4(3) . . . .
V1 O1 C1 C2 169.54(16) . . . .
C5 N3 C2 C3 0.4(3) . . . .
C6 N3 C2 C3 178.7(2) . . . .
C5 N3 C2 C1 178.9(2) . . . .
C6 N3 C2 C1 -2.7(4) . . . .
N1 C1 C2 C3 179.3(2) . . . .
O1 C1 C2 C3 0.4(4) . . . .
N1 C1 C2 N3 1.0(4) . . . .
O1 C1 C2 N3 -177.9(2) . . . .
N3 C2 C3 C4 0.0(3) . . . .
C1 C2 C3 C4 -178.6(2) . . . .
C2 C3 C4 C5 -0.3(3) . . . .
C2 C3 C4 N4 -179.3(2) . . . .
O3 N4 C4 C5 -8.4(4) . . . .
O2 N4 C4 C5 171.1(3) . . . .
O3 N4 C4 C3 170.5(3) . . . .
O2 N4 C4 C3 -10.0(4) . . . .
C2 N3 C5 C4 -0.6(3) . . . .
C6 N3 C5 C4 -179.0(2) . . . .
C3 C4 C5 N3 0.6(3) . . . .
N4 C4 C5 N3 179.6(2) . . . .
N1 N2 C7 C8 177.5(2) . . . .
V1 N2 C7 C8 -8.7(4) . . . .
N2 C7 C8 C9 -10.8(4) . . . .
N2 C7 C8 C13 172.1(3) . . . .
V1 O4 C9 C10 -146.3(2) . . . .
V1 O4 C9 C8 36.2(3) . . . .
C13 C8 C9 O4 177.1(2) . . . .
C7 C8 C9 O4 0.0(4) . . . .
C13 C8 C9 C10 -0.4(4) . . . .
C7 C8 C9 C10 -177.6(2) . . . .
O4 C9 C10 C11 -178.3(2) . . . .
C8 C9 C10 C11 -0.7(4) . . . .
C9 C10 C11 C12 1.3(5) . . . .
C10 C11 C12 C13 -0.6(5) . . . .
C11 C12 C13 C8 -0.6(5) . . . .
C9 C8 C13 C12 1.1(4) . . . .
C7 C8 C13 C12 178.2(3) . . . .
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139049052
