#------------------------------------------------------------------------------
#$Date: 2024-07-05 19:19:15 +0300 (Fri, 05 Jul 2024) $
#$Revision: 293056 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/71/58/7715869.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_7715869
loop_
_publ_author_name
'Martins, Francisco Mainardi'
'Iglesias, Bernardo Almeida'
'Chaves, Otávio Augusto'
'Gutknecht da Silva, Jean Lucas'
'Leal, Daniela Bitencourt Rosa'
'Back, Davi Fernando'
_publ_section_title
;
 Vanadium(V) complexes derived from triphenylphosphonium and hydrazides:
 cytotoxicity evaluation and interaction with biomolecules.
;
_journal_issue                   19
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_page_first              8315
_journal_page_last               8327
_journal_paper_doi               10.1039/d4dt00464g
_journal_volume                  53
_journal_year                    2024
_chemical_formula_moiety         'C33 H25 F N2 O4 P V, C H4 O, H2 O'
_chemical_formula_sum            'C34 H31 F N2 O6 P V'
_chemical_formula_weight         664.52
_chemical_melting_point          448
_chemical_name_common            '[VO2(L50]CH3OH H2O'
_chemical_name_systematic
'3-{[2-(4-fluorobenzoyl)hydrazono]methyl}-4-hydroxybenzyl}        triphenylphosphonium chloride vanadium (V) dioxido complex'
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_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_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4
_audit_creation_date             2024-02-02T15:09:37-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_update_record
;
2024-03-27 deposited with the CCDC.	2024-04-17 downloaded from the CCDC.
;
_cell_angle_alpha                88.136(2)
_cell_angle_beta                 88.887(2)
_cell_angle_gamma                75.909(2)
_cell_formula_units_Z            2
_cell_length_a                   9.9185(5)
_cell_length_b                   10.6629(4)
_cell_length_c                   15.2191(8)
_cell_measurement_reflns_used    9905
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      28.273
_cell_measurement_theta_min      2.501
_cell_volume                     1560.20(13)
_computing_cell_refinement       'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_data_collection       'Bruker Instrument Service v4.2.7'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_molecular_graphics    'Diamond (version 3.2i; Crystal Impact GbR'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXL97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 10.4167
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker D8 Quest Photon 100 diffractometer'
_diffrn_measurement_method       '2° φ & ω scans'
_diffrn_radiation_monochromator  'Montel type 2-dim beam shaping X ray optics'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0378
_diffrn_reflns_av_unetI/netI     0.0383
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            31886
_diffrn_reflns_theta_full        28.31
_diffrn_reflns_theta_max         28.31
_diffrn_reflns_theta_min         1.97
_diffrn_source                   'micro-focus tube'
_exptl_absorpt_coefficient_mu    0.424
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.6744
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
        SADABS (version 2012/1; Bruker, 2012) was used to perform the
        numerical absorption correction based on the indexed faces
        of the crystal.
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.415
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       tabular
_exptl_crystal_F_000             688
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.842
_refine_diff_density_min         -0.842
_refine_diff_density_rms         0.121
_refine_ls_extinction_coef       none
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     408
_refine_ls_number_reflns         7748
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.063
_refine_ls_R_factor_all          0.0803
_refine_ls_R_factor_gt           0.0627
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0047P)²+3.3149P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1816
_refine_ls_wR_factor_ref         0.1935
_reflns_number_gt                6277
_reflns_number_total             7748
_reflns_threshold_expression     >2σ(I)
_cod_data_source_file            d4dt00464g2.cif
_cod_data_source_block           C5
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_chemical_melting_point' value '448K' was changed to '448'
-- the value should be numeric and without a unit designator.

data item '_exptl_crystal_density_meas' value 'none' was changed to
'?' -- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 8170 2020-07-09 18:12:32Z antanas 

 Adding full bibliography for 7715863--7715870.cif.
;
_cod_original_sg_symbol_Hall     -P1
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               7715869
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
V V 0.44187(5) 0.63530(5) 0.23818(3) 0.01477(15) Uani 1 1 d . . .
P P 0.61636(8) 0.83396(7) 0.73627(5) 0.01452(17) Uani 1 1 d . . .
F F 0.9888(3) 0.1056(2) -0.06213(15) 0.0469(6) Uani 1 1 d . . .
O1 O 0.3747(2) 0.6831(2) 0.35507(13) 0.0199(4) Uani 1 1 d . . .
O2 O 0.5524(2) 0.5074(2) 0.15657(13) 0.0196(4) Uani 1 1 d . . .
O3 O 0.4543(3) 0.7711(2) 0.19214(15) 0.0245(5) Uani 1 1 d . . .
O4 O 0.2959(2) 0.6021(2) 0.20898(14) 0.0235(5) Uani 1 1 d . . .
O5 O 0.0016(4) 0.5082(5) 0.2460(3) 0.0766(12) Uani 1 1 d . . .
H5A H -0.0735 0.4894 0.2604 0.115 Uiso 1 1 calc R . .
O6 O 0.1023(4) 0.6294(4) 0.3797(3) 0.0751(12) Uani 1 1 d . . .
N1 N 0.6250(2) 0.5366(2) 0.30793(16) 0.0154(5) Uani 1 1 d . . .
N2 N 0.7250(3) 0.4488(2) 0.25922(17) 0.0195(5) Uani 1 1 d . . .
C2 C 0.5690(3) 0.6217(3) 0.45261(18) 0.0147(5) Uani 1 1 d . . .
C3 C 0.6189(3) 0.6246(3) 0.53872(18) 0.0159(5) Uani 1 1 d . . .
H3 H 0.7125 0.5816 0.5514 0.019 Uiso 1 1 calc R . .
C4 C 0.5351(3) 0.6884(3) 0.60469(18) 0.0160(5) Uani 1 1 d . . .
C5 C 0.3963(3) 0.7503(3) 0.58511(19) 0.0182(6) Uani 1 1 d . . .
H5 H 0.3366 0.793 0.6302 0.022 Uiso 1 1 calc R . .
C6 C 0.3455(3) 0.7498(3) 0.5012(2) 0.0190(6) Uani 1 1 d . . .
H6 H 0.2518 0.7934 0.4893 0.023 Uiso 1 1 calc R . .
C7 C 0.5872(3) 0.6832(3) 0.69797(18) 0.0179(6) Uani 1 1 d . . .
H7A H 0.6755 0.6159 0.7023 0.021 Uiso 1 1 calc R . .
H7B H 0.5189 0.6561 0.7379 0.021 Uiso 1 1 calc R . .
C8 C 0.4633(3) 0.9596(3) 0.7156(2) 0.0204(6) Uani 1 1 d . . .
C9 C 0.3524(4) 0.9742(4) 0.7747(2) 0.0333(8) Uani 1 1 d . . .
H9 H 0.3614 0.9242 0.828 0.04 Uiso 1 1 calc R . .
C10 C 0.2269(4) 1.0635(5) 0.7546(3) 0.0491(13) Uani 1 1 d . . .
H10 H 0.1507 1.0752 0.7948 0.059 Uiso 1 1 calc R . .
C11 C 0.2144(4) 1.1345(4) 0.6760(4) 0.0501(13) Uani 1 1 d . . .
H11 H 0.1294 1.1952 0.6628 0.06 Uiso 1 1 calc R . .
C12 C 0.3234(4) 1.1181(4) 0.6171(4) 0.0457(11) Uani 1 1 d . . .
H12 H 0.313 1.1664 0.5631 0.055 Uiso 1 1 calc R . .
C13 C 0.4488(4) 1.0311(3) 0.6362(3) 0.0316(8) Uani 1 1 d . . .
H13 H 0.5243 1.0202 0.5956 0.038 Uiso 1 1 calc R . .
C14 C 0.6442(3) 0.8171(3) 0.85251(18) 0.0188(6) Uani 1 1 d . . .
C15 C 0.6441(3) 0.9290(3) 0.8987(2) 0.0225(6) Uani 1 1 d . . .
H15 H 0.6289 1.0107 0.8687 0.027 Uiso 1 1 calc R . .
C16 C 0.6661(3) 0.9190(3) 0.9885(2) 0.0268(7) Uani 1 1 d . . .
H16 H 0.6691 0.9937 1.02 0.032 Uiso 1 1 calc R . .
C17 C 0.6838(4) 0.8009(4) 1.0323(2) 0.0323(8) Uani 1 1 d . . .
H17 H 0.6946 0.7954 1.0943 0.039 Uiso 1 1 calc R . .
C18 C 0.6858(5) 0.6905(4) 0.9865(2) 0.0435(11) Uani 1 1 d . . .
H18 H 0.6997 0.6094 1.0172 0.052 Uiso 1 1 calc R . .
C19 C 0.6676(5) 0.6971(4) 0.8955(2) 0.0347(9) Uani 1 1 d . . .
H19 H 0.6712 0.6211 0.8637 0.042 Uiso 1 1 calc R . .
C20 C 0.7638(3) 0.8736(3) 0.68217(18) 0.0165(5) Uani 1 1 d . . .
C21 C 0.7808(3) 0.9993(3) 0.6861(2) 0.0238(6) Uani 1 1 d . . .
H21 H 0.7112 1.0645 0.7132 0.029 Uiso 1 1 calc R . .
C22 C 0.8990(3) 1.0290(3) 0.6506(2) 0.0277(7) Uani 1 1 d . . .
H22 H 0.9111 1.1145 0.6533 0.033 Uiso 1 1 calc R . .
C23 C 0.9998(3) 0.9336(4) 0.6110(2) 0.0296(7) Uani 1 1 d . . .
H23 H 1.0812 0.9539 0.5869 0.036 Uiso 1 1 calc R . .
C24 C 0.9828(4) 0.8085(4) 0.6062(3) 0.0365(9) Uani 1 1 d . . .
H24 H 1.0517 0.7438 0.5783 0.044 Uiso 1 1 calc R . .
C25 C 0.8648(3) 0.7783(3) 0.6425(2) 0.0272(7) Uani 1 1 d . . .
H25 H 0.8532 0.6926 0.6401 0.033 Uiso 1 1 calc R . .
C26 C 0.6596(3) 0.5460(3) 0.38862(19) 0.0164(5) Uani 1 1 d . . .
H26 H 0.7499 0.5004 0.4066 0.02 Uiso 1 1 calc R . .
C27 C 0.6743(3) 0.4408(3) 0.18136(18) 0.0158(5) Uani 1 1 d . . .
C28 C 0.7569(3) 0.3487(3) 0.11862(19) 0.0188(6) Uani 1 1 d . . .
C29 C 0.8892(4) 0.2746(4) 0.1397(2) 0.0293(7) Uani 1 1 d . . .
H29 H 0.9259 0.281 0.1962 0.035 Uiso 1 1 calc R . .
C30 C 0.9678(4) 0.1918(4) 0.0795(3) 0.0370(9) Uani 1 1 d . . .
H30 H 1.0584 0.1419 0.0934 0.044 Uiso 1 1 calc R . .
C31 C 0.9104(4) 0.1838(4) -0.0016(2) 0.0312(8) Uani 1 1 d . . .
C32 C 0.7792(4) 0.2509(3) -0.0244(2) 0.0304(8) Uani 1 1 d . . .
H32 H 0.742 0.2403 -0.08 0.036 Uiso 1 1 calc R . .
C33 C 0.7021(4) 0.3351(3) 0.0364(2) 0.0243(7) Uani 1 1 d . . .
H33 H 0.6113 0.3839 0.0219 0.029 Uiso 1 1 calc R . .
C34 C -0.0136(6) 0.5752(6) 0.1625(5) 0.0718(18) Uani 1 1 d . . .
H34A H 0.0381 0.6427 0.1621 0.108 Uiso 1 1 calc R . .
H34B H -0.1122 0.6148 0.1522 0.108 Uiso 1 1 calc R . .
H34C H 0.023 0.514 0.1161 0.108 Uiso 1 1 calc R . .
C1 C 0.4303(3) 0.6858(3) 0.43326(18) 0.0159(5) Uani 1 1 d . . .
H6B H 0.0327 0.6179 0.4313 0.05 Uiso 1 1 d D . .
H6A H 0.0744 0.5823 0.3204 0.05 Uiso 1 1 d 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 0 '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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.1023 0.0942 '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
_geom_angle_publ_flag
O3 V O4 109.66(12) . . ?
O3 V O1 103.44(11) . . ?
O4 V O1 93.64(10) . . ?
O3 V O2 102.01(10) . . ?
O4 V O2 91.89(10) . . ?
O1 V O2 150.37(9) . . ?
O3 V N1 113.45(11) . . ?
O4 V N1 136.44(11) . . ?
O1 V N1 82.43(9) . . ?
O2 V N1 73.65(9) . . ?
C8 P C14 108.83(15) . . ?
C8 P C20 110.01(14) . . ?
C14 P C20 109.77(14) . . ?
C8 P C7 108.34(14) . . ?
C14 P C7 108.24(14) . . ?
C20 P C7 111.59(14) . . ?
C1 O1 V 136.52(19) . . ?
C27 O2 V 118.38(18) . . ?
C26 N1 N2 114.0(2) . . ?
C26 N1 V 130.1(2) . . ?
N2 N1 V 115.95(17) . . ?
C27 N2 N1 108.2(2) . . ?
C1 C2 C3 119.5(3) . . ?
C1 C2 C26 121.9(3) . . ?
C3 C2 C26 118.5(3) . . ?
C4 C3 C2 121.6(3) . . ?
C3 C4 C5 118.5(3) . . ?
C3 C4 C7 120.9(3) . . ?
C5 C4 C7 120.4(3) . . ?
C6 C5 C4 121.0(3) . . ?
C5 C6 C1 121.0(3) . . ?
C4 C7 P 115.2(2) . . ?
C9 C8 C13 120.3(3) . . ?
C9 C8 P 118.8(3) . . ?
C13 C8 P 120.4(3) . . ?
C8 C9 C10 119.2(4) . . ?
C11 C10 C9 119.9(4) . . ?
C12 C11 C10 120.7(4) . . ?
C11 C12 C13 120.2(4) . . ?
C12 C13 C8 119.7(4) . . ?
C19 C14 C15 120.9(3) . . ?
C19 C14 P 121.2(2) . . ?
C15 C14 P 117.9(2) . . ?
C16 C15 C14 119.3(3) . . ?
C17 C16 C15 120.2(3) . . ?
C16 C17 C18 120.4(3) . . ?
C17 C18 C19 120.6(4) . . ?
C14 C19 C18 118.6(3) . . ?
C25 C20 C21 120.2(3) . . ?
C25 C20 P 120.4(2) . . ?
C21 C20 P 119.2(2) . . ?
C22 C21 C20 119.9(3) . . ?
C21 C22 C23 119.8(3) . . ?
C22 C23 C24 120.6(3) . . ?
C25 C24 C23 119.8(3) . . ?
C20 C25 C24 119.8(3) . . ?
N1 C26 C2 123.7(3) . . ?
O2 C27 N2 123.4(3) . . ?
O2 C27 C28 117.6(2) . . ?
N2 C27 C28 119.0(3) . . ?
C29 C28 C33 119.0(3) . . ?
C29 C28 C27 121.2(3) . . ?
C33 C28 C27 119.8(3) . . ?
C30 C29 C28 120.8(3) . . ?
C31 C30 C29 118.0(3) . . ?
F C31 C32 118.2(3) . . ?
F C31 C30 118.3(3) . . ?
C32 C31 C30 123.5(3) . . ?
C31 C32 C33 117.8(3) . . ?
C32 C33 C28 120.8(3) . . ?
O1 C1 C6 118.6(3) . . ?
O1 C1 C2 122.9(3) . . ?
C6 C1 C2 118.4(3) . . ?
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
V O3 1.619(2) . ?
V O4 1.644(2) . ?
V O1 1.928(2) . ?
V O2 1.983(2) . ?
V N1 2.146(2) . ?
P C8 1.789(3) . ?
P C14 1.792(3) . ?
P C20 1.796(3) . ?
P C7 1.817(3) . ?
F C31 1.363(4) . ?
O1 C1 1.325(3) . ?
O2 C27 1.300(4) . ?
O5 C34 1.430(7) . ?
N1 C26 1.295(4) . ?
N1 N2 1.405(3) . ?
N2 C27 1.309(4) . ?
C2 C1 1.412(4) . ?
C2 C3 1.414(4) . ?
C2 C26 1.439(4) . ?
C3 C4 1.378(4) . ?
C4 C5 1.408(4) . ?
C4 C7 1.515(4) . ?
C5 C6 1.382(4) . ?
C6 C1 1.406(4) . ?
C8 C9 1.389(5) . ?
C8 C13 1.398(5) . ?
C9 C10 1.403(6) . ?
C10 C11 1.385(8) . ?
C11 C12 1.373(7) . ?
C12 C13 1.387(5) . ?
C14 C19 1.387(5) . ?
C14 C15 1.405(4) . ?
C15 C16 1.384(4) . ?
C16 C17 1.380(5) . ?
C17 C18 1.383(6) . ?
C18 C19 1.398(5) . ?
C20 C25 1.386(4) . ?
C20 C21 1.395(4) . ?
C21 C22 1.383(4) . ?
C22 C23 1.385(5) . ?
C23 C24 1.389(5) . ?
C24 C25 1.387(5) . ?
C27 C28 1.478(4) . ?
C28 C29 1.395(5) . ?
C28 C33 1.399(4) . ?
C29 C30 1.385(5) . ?
C30 C31 1.382(5) . ?
C31 C32 1.369(5) . ?
C32 C33 1.394(4) . ?
