#------------------------------------------------------------------------------
#$Date: 2025-08-21 22:04:39 +0200 (Thu 21 de Aug de 2025) $
#$Revision: 301851 $
#$URL: svn://www.crystallography.net/cod/cif/7/05/69/7056950.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_7056950
loop_
_publ_author_name
'Koleša Dobravc, Tanja'
'Maejima, Keiichi'
'Yoshikawa, Yutaka'
'Meden, Anton'
'Yasui, Hiroyuki'
'Perdih, Franc'
_publ_section_title
;
 Bis(picolinato) complexes of vanadium and zinc as potential antidiabetic
 agents: synthesis, structural elucidation and in vitro insulin-mimetic
 activity study
;
_journal_issue                   5
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              3619
_journal_page_last               3632
_journal_paper_doi               10.1039/C7NJ04189F
_journal_volume                  42
_journal_year                    2018
_chemical_formula_moiety         'C24 H12 F4 N4 O4 Zn, 2(C H Cl3)'
_chemical_formula_sum            'C26 H14 Cl6 F4 N4 O4 Zn'
_chemical_formula_weight         800.48
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2017-09-12 deposited with the CCDC.
2018-01-24 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 126.182(8)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.9576(8)
_cell_length_b                   28.0951(7)
_cell_length_c                   10.7178(5)
_cell_measurement_reflns_used    3853
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      30.4686
_cell_measurement_theta_min      2.7932
_cell_volume                     3149.3(4)
_computing_cell_refinement       'CrysAlis PRO (Agilent, 2011)'
_computing_data_collection       'CrysAlis PRO (Agilent, 2011)'
_computing_data_reduction        'CrysAlis PRO (Agilent, 2011)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2015)'
_computing_structure_solution    'SIR97 (Altomare et al., 1999)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 10.4933
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  Mirror
_diffrn_radiation_source         'SuperNova (Mo) X-ray Source'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0319
_diffrn_reflns_av_unetI/netI     0.0271
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       36
_diffrn_reflns_limit_k_min       -36
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            14737
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.482
_diffrn_reflns_theta_min         2.920
_exptl_absorpt_coefficient_mu    1.353
_exptl_absorpt_correction_T_max  0.8995
_exptl_absorpt_correction_T_min  0.7736
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(CrysAlis PRO; Agilent, 2013)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.688
_exptl_crystal_description       prism
_exptl_crystal_F_000             1592
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.130
_exptl_crystal_size_min          0.080
_refine_diff_density_max         0.560
_refine_diff_density_min         -0.550
_refine_diff_density_rms         0.056
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     232
_refine_ls_number_reflns         3602
_refine_ls_number_restraints     61
_refine_ls_restrained_S_all      1.222
_refine_ls_R_factor_all          0.0699
_refine_ls_R_factor_gt           0.0521
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0460P)²+6.7139P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1220
_refine_ls_wR_factor_ref         0.1335
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2795
_reflns_number_total             3602
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c7nj04189f2.cif
_cod_data_source_block           8
_cod_database_code               7056950
#BEGIN Tags that were not found in dictionaries:
_shelx_shelxl_version_number     2014/7
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_min   0.774
_shelx_estimated_absorpt_t_max   0.899
#END Tags that were not found in dictionaries
loop_
_space_group_symop_operation_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Zn1 Zn 1.0000 0.86497(2) 0.2500 0.05023(18) Uani 1 2 d S T P . .
F1 F 1.4083(2) 0.97667(11) 0.5726(3) 0.1057(9) Uani 1 1 d . . . . .
F2 F 1.1337(2) 0.99023(9) 0.7188(3) 0.0867(7) Uani 1 1 d . . . . .
N1 N 1.1149(3) 0.91713(8) 0.4351(3) 0.0488(6) Uani 1 1 d . . . . .
N2 N 0.9312(3) 0.80483(9) 0.0941(3) 0.0509(6) Uani 1 1 d . . . . .
O1 O 1.1537(2) 0.87540(8) 0.2448(2) 0.0568(6) Uani 1 1 d . . . . .
O2 O 1.3365(3) 0.91334(10) 0.3456(3) 0.0780(8) Uani 1 1 d . . . . .
C1 C 1.2411(3) 0.90431(11) 0.3381(3) 0.0510(7) Uani 1 1 d . . . . .
C2 C 1.2208(3) 0.92911(10) 0.4491(3) 0.0490(7) Uani 1 1 d . . . . .
C3 C 1.3023(3) 0.96312(13) 0.5577(4) 0.0637(9) Uani 1 1 d . . . . .
C4 C 1.2764(4) 0.98446(14) 0.6525(4) 0.0711(10) Uani 1 1 d . . . . .
H4 H 1.3309 1.0070 0.7261 0.085 Uiso 1 1 calc R U . . .
C5 C 1.1670(4) 0.97067(12) 0.6323(4) 0.0619(9) Uani 1 1 d . . . . .
C6 C 1.0868(3) 0.93709(11) 0.5242(4) 0.0558(8) Uani 1 1 d . . . . .
H6 H 1.0127 0.9283 0.5134 0.067 Uiso 1 1 calc R U . . .
C7 C 0.8642(4) 0.80509(12) -0.0587(4) 0.0631(9) Uani 1 1 d . . . . .
H7 H 0.8417 0.8342 -0.1096 0.076 Uiso 1 1 calc R U . . .
C8 C 0.8261(4) 0.76353(13) -0.1463(4) 0.0705(10) Uani 1 1 d . . . . .
H8 H 0.7785 0.7652 -0.2534 0.085 Uiso 1 1 calc R U . . .
C9 C 0.8587(4) 0.72091(13) -0.0749(4) 0.0678(10) Uani 1 1 d . . . . .
H9 H 0.8339 0.6930 -0.1325 0.081 Uiso 1 1 calc R U . . .
C10 C 0.9302(3) 0.71885(11) 0.0870(4) 0.0551(8) Uani 1 1 d . . . . .
C11 C 0.9639(3) 0.76215(10) 0.1667(3) 0.0457(6) Uani 1 1 d . . . . .
C12 C 0.9674(4) 0.67528(12) 0.1724(4) 0.0701(10) Uani 1 1 d . . . . .
H12 H 0.9461 0.6464 0.1200 0.084 Uiso 1 1 calc R U . . .
Cl1A Cl 0.6098(3) 0.89460(15) 0.4727(4) 0.1508(15) Uani 0.598(5) 1 d D U P A 1
Cl2A Cl 0.8686(3) 0.8771(3) 0.6163(4) 0.223(3) Uani 0.598(5) 1 d D U P A 1
Cl3A Cl 0.6813(8) 0.80611(11) 0.4392(5) 0.220(4) Uani 0.598(5) 1 d D U P A 1
Cl1B Cl 0.6125(5) 0.8361(5) 0.4549(11) 0.309(8) Uani 0.402(5) 1 d D U P A 2
Cl2B Cl 0.8105(8) 0.90697(18) 0.5752(6) 0.183(3) Uani 0.402(5) 1 d D U P A 2
Cl3B Cl 0.8443(5) 0.81461(16) 0.5289(5) 0.1299(19) Uani 0.402(5) 1 d D U P A 2
C13 C 0.7254(4) 0.86201(17) 0.4600(5) 0.1025(16) Uani 1 1 d D . . . .
H13 H 0.7179 0.8724 0.3677 0.154 Uiso 1 1 calc R U . A 1
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'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Zn Zn 0.2839 1.4301 '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
O1 Zn1 O1 163.53(12) . 2_755
O1 Zn1 N2 93.14(9) . .
O1 Zn1 N2 99.72(10) 2_755 .
O1 Zn1 N2 99.72(10) . 2_755
O1 Zn1 N2 93.14(9) 2_755 2_755
N2 Zn1 N2 77.32(13) . 2_755
O1 Zn1 N1 91.82(9) . 2_755
O1 Zn1 N1 77.12(9) 2_755 2_755
N2 Zn1 N1 94.18(9) . 2_755
N2 Zn1 N1 165.96(10) 2_755 2_755
O1 Zn1 N1 77.12(9) . .
O1 Zn1 N1 91.81(9) 2_755 .
N2 Zn1 N1 165.96(10) . .
N2 Zn1 N1 94.19(9) 2_755 .
N1 Zn1 N1 96.19(13) 2_755 .
C6 N1 C2 120.9(3) . .
C6 N1 Zn1 127.1(2) . .
C2 N1 Zn1 111.98(19) . .
C7 N2 C11 118.0(3) . .
C7 N2 Zn1 128.3(2) . .
C11 N2 Zn1 113.67(18) . .
C1 O1 Zn1 120.1(2) . .
O2 C1 O1 125.9(3) . .
O2 C1 C2 119.2(3) . .
O1 C1 C2 114.9(3) . .
N1 C2 C3 119.4(3) . .
N1 C2 C1 115.8(3) . .
C3 C2 C1 124.8(3) . .
F1 C3 C4 117.7(3) . .
F1 C3 C2 120.9(3) . .
C4 C3 C2 121.4(3) . .
C5 C4 C3 116.3(3) . .
C5 C4 H4 121.9 . .
C3 C4 H4 121.9 . .
F2 C5 C4 120.1(3) . .
F2 C5 C6 118.0(3) . .
C4 C5 C6 121.9(3) . .
N1 C6 C5 120.2(3) . .
N1 C6 H6 119.9 . .
C5 C6 H6 119.9 . .
N2 C7 C8 122.7(3) . .
N2 C7 H7 118.6 . .
C8 C7 H7 118.6 . .
C9 C8 C7 119.6(3) . .
C9 C8 H8 120.2 . .
C7 C8 H8 120.2 . .
C8 C9 C10 119.7(3) . .
C8 C9 H9 120.2 . .
C10 C9 H9 120.2 . .
C11 C10 C9 117.3(3) . .
C11 C10 C12 119.2(3) . .
C9 C10 C12 123.5(3) . .
N2 C11 C10 122.7(3) . .
N2 C11 C11 117.66(15) . 2_755
C10 C11 C11 119.64(18) . 2_755
C12 C12 C10 121.19(18) 2_755 .
C12 C12 H12 119.4 2_755 .
C10 C12 H12 119.4 . .
Cl1B C13 Cl2B 124.4(7) . .
Cl3A C13 Cl2A 118.3(4) . .
Cl3A C13 Cl1A 104.8(4) . .
Cl2A C13 Cl1A 105.9(3) . .
Cl1B C13 Cl3B 102.5(5) . .
Cl2B C13 Cl3B 102.9(4) . .
Cl3A C13 H13 109.2 . .
Cl2A C13 H13 109.2 . .
Cl1A C13 H13 109.2 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Zn1 O1 2.046(2) .
Zn1 O1 2.046(2) 2_755
Zn1 N2 2.164(2) .
Zn1 N2 2.164(2) 2_755
Zn1 N1 2.194(2) 2_755
Zn1 N1 2.194(2) .
F1 C3 1.340(4) .
F2 C5 1.348(4) .
N1 C6 1.330(4) .
N1 C2 1.333(4) .
N2 C7 1.326(4) .
N2 C11 1.354(4) .
O1 C1 1.267(4) .
O2 C1 1.218(4) .
C1 C2 1.530(4) .
C2 C3 1.389(5) .
C3 C4 1.381(5) .
C4 C5 1.359(5) .
C4 H4 0.9300 .
C5 C6 1.375(5) .
C6 H6 0.9300 .
C7 C8 1.393(5) .
C7 H7 0.9300 .
C8 C9 1.347(5) .
C8 H8 0.9300 .
C9 C10 1.405(5) .
C9 H9 0.9300 .
C10 C11 1.400(4) .
C10 C12 1.431(5) .
C11 C11 1.446(5) 2_755
C12 C12 1.349(7) 2_755
C12 H12 0.9300 .
Cl1A C13 1.828(5) .
Cl2A C13 1.661(5) .
Cl3A C13 1.641(6) .
Cl1B C13 1.606(7) .
Cl2B C13 1.652(7) .
Cl3B C13 1.830(5) .
C13 H13 0.9800 .
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C4 H4 O2 0.93 2.56 3.351(5) 143.5 6_576
C13 H13 O1 0.98 2.57 3.388(5) 141.1 2_755
C13 H13 O2 0.98 2.27 3.217(5) 162.8 2_755
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_4
Zn1 O1 C1 O2 180.0(3) .
Zn1 O1 C1 C2 0.2(3) .
C6 N1 C2 C3 -0.4(4) .
Zn1 N1 C2 C3 177.8(2) .
C6 N1 C2 C1 -178.9(3) .
Zn1 N1 C2 C1 -0.8(3) .
O2 C1 C2 N1 -179.4(3) .
O1 C1 C2 N1 0.4(4) .
O2 C1 C2 C3 2.2(5) .
O1 C1 C2 C3 -178.0(3) .
N1 C2 C3 F1 -178.7(3) .
C1 C2 C3 F1 -0.3(5) .
N1 C2 C3 C4 0.6(5) .
C1 C2 C3 C4 179.0(3) .
F1 C3 C4 C5 178.7(3) .
C2 C3 C4 C5 -0.6(6) .
C3 C4 C5 F2 -179.1(3) .
C3 C4 C5 C6 0.5(6) .
C2 N1 C6 C5 0.2(5) .
Zn1 N1 C6 C5 -177.7(2) .
F2 C5 C6 N1 179.3(3) .
C4 C5 C6 N1 -0.2(5) .
C11 N2 C7 C8 0.3(5) .
Zn1 N2 C7 C8 179.6(3) .
N2 C7 C8 C9 -0.6(6) .
C7 C8 C9 C10 0.2(6) .
C8 C9 C10 C11 0.3(6) .
C8 C9 C10 C12 179.0(4) .
C7 N2 C11 C10 0.2(5) .
Zn1 N2 C11 C10 -179.2(2) .
C7 N2 C11 C11 -179.4(4) 2_755
Zn1 N2 C11 C11 1.2(4) 2_755
C9 C10 C11 N2 -0.5(5) .
C12 C10 C11 N2 -179.3(3) .
C9 C10 C11 C11 179.1(4) 2_755
C12 C10 C11 C11 0.4(6) 2_755
C11 C10 C12 C12 0.8(7) 2_755
C9 C10 C12 C12 -177.9(5) 2_755
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139178310
