#------------------------------------------------------------------------------
#$Date: 2024-07-05 19:19:15 +0300 (Fri, 05 Jul 2024) $
#$Revision: 293056 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/71/58/7715867.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_7715867
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         'C32 H27 N3 O2 P, Cl'
_chemical_formula_sum            'C32 H27 Cl N3 O2 P'
_chemical_formula_weight         551.99
_chemical_melting_point          522
_chemical_name_common            '[H2L2]Cl'
_chemical_name_systematic
'{4-hydroxy-3-[(2-nicotinoylhydrazono)methyl]benzyl}        triphenylphosphonium chloride'
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 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             2024-03-19T12:33:03-00:00
_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                90
_cell_angle_beta                 102.2020(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.6944(5)
_cell_length_b                   10.2221(4)
_cell_length_c                   23.3093(8)
_cell_measurement_reflns_used    6085
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.899
_cell_measurement_theta_min      2.241
_cell_volume                     2723.48(18)
_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 0.998
_diffrn_measured_fraction_theta_max 0.998
_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  0.1037
_diffrn_reflns_av_unetI/netI     0.09
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            36928
_diffrn_reflns_theta_full        28.36
_diffrn_reflns_theta_max         28.36
_diffrn_reflns_theta_min         2.18
_diffrn_source                   'micro-focus tube'
_exptl_absorpt_coefficient_mu    0.235
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.7121
_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            colourless
_exptl_crystal_density_diffrn    1.346
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1152
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.315
_refine_diff_density_min         -0.345
_refine_diff_density_rms         0.07
_refine_ls_extinction_coef       none
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     360
_refine_ls_number_reflns         6805
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.027
_refine_ls_R_factor_all          0.1123
_refine_ls_R_factor_gt           0.0571
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0352P)²+1.6291P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0934
_refine_ls_wR_factor_ref         0.1078
_reflns_number_gt                4430
_reflns_number_total             6805
_reflns_threshold_expression     >2σ(I)
_cod_data_source_file            d4dt00464g2.cif
_cod_data_source_block           H2L2Cl
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_chemical_melting_point' value '522K' was changed to '522'
-- 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_cell_volume        2723.47(18)
_cod_original_sg_symbol_Hall     -P2ybc
_cod_original_sg_symbol_H-M      P21/c
_cod_database_code               7715867
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl Cl 0.41823(5) 0.06137(6) 0.68139(2) 0.02096(14) Uani 1 1 d . . .
P P 0.64777(5) 0.70771(6) 0.65266(2) 0.01299(13) Uani 1 1 d . . .
O1 O 0.12496(13) 0.50362(17) 0.52720(7) 0.0255(4) Uani 1 1 d . . .
H1 H 0.1098 0.4292 0.539 0.031 Uiso 1 1 calc R . .
O2 O -0.03690(14) 0.15965(16) 0.56297(7) 0.0259(4) Uani 1 1 d . . .
N1 N 0.16756(16) 0.29014(18) 0.59503(8) 0.0195(4) Uani 1 1 d . . .
N2 N 0.15507(17) 0.16027(19) 0.60898(9) 0.0196(4) Uani 1 1 d . . .
N3 N 0.10974(17) -0.2287(2) 0.66436(8) 0.0244(5) Uani 1 1 d . . .
C1 C 0.21964(18) 0.5541(2) 0.56469(9) 0.0177(5) Uani 1 1 d . . .
C9 C 0.04656(18) -0.0406(2) 0.60390(9) 0.0178(5) Uani 1 1 d . . .
C10 C 0.1140(2) -0.1009(2) 0.65283(10) 0.0210(5) Uani 1 1 d . . .
C11 C 0.0356(2) -0.3001(2) 0.62465(11) 0.0270(6) Uani 1 1 d . . .
H11 H 0.0322 -0.3916 0.6312 0.032 Uiso 1 1 calc R . .
C12 C -0.0359(2) -0.2495(2) 0.57505(10) 0.0263(6) Uani 1 1 d . . .
H12 H -0.0871 -0.3047 0.5486 0.032 Uiso 1 1 calc R . .
C13 C -0.03141(19) -0.1172(2) 0.56462(10) 0.0218(5) Uani 1 1 d . . .
H13 H -0.0807 -0.0789 0.5312 0.026 Uiso 1 1 calc R . .
C15 C 0.68502(17) 0.5377(2) 0.64798(9) 0.0148(5) Uani 1 1 d . . .
C16 C 0.66529(18) 0.4502(2) 0.69052(10) 0.0194(5) Uani 1 1 d . . .
H16 H 0.6291 0.4793 0.7211 0.023 Uiso 1 1 calc R . .
C17 C 0.6985(2) 0.3207(2) 0.68822(10) 0.0243(6) Uani 1 1 d . . .
H17 H 0.6834 0.2603 0.7167 0.029 Uiso 1 1 calc R . .
C18 C 0.7538(2) 0.2789(2) 0.64419(10) 0.0262(6) Uani 1 1 d . . .
H18 H 0.7757 0.1898 0.6425 0.031 Uiso 1 1 calc R . .
C19 C 0.7771(2) 0.3665(3) 0.60294(10) 0.0261(6) Uani 1 1 d . . .
H19 H 0.8176 0.3382 0.5739 0.031 Uiso 1 1 calc R . .
C20 C 0.74138(18) 0.4957(2) 0.60402(10) 0.0198(5) Uani 1 1 d . . .
H20 H 0.7551 0.5554 0.575 0.024 Uiso 1 1 calc R . .
C21 C 0.76309(18) 0.7867(2) 0.70375(9) 0.0153(5) Uani 1 1 d . . .
C22 C 0.86488(18) 0.7175(2) 0.72719(9) 0.0189(5) Uani 1 1 d . . .
H22 H 0.8732 0.6293 0.7158 0.023 Uiso 1 1 calc R . .
C23 C 0.95407(19) 0.7776(2) 0.76718(10) 0.0237(5) Uani 1 1 d . . .
H23 H 1.0233 0.7304 0.7836 0.028 Uiso 1 1 calc R . .
C24 C 0.9420(2) 0.9061(2) 0.78303(10) 0.0238(6) Uani 1 1 d . . .
H24 H 1.004 0.9474 0.8098 0.029 Uiso 1 1 calc R . .
C25 C 0.84078(19) 0.9758(2) 0.76053(10) 0.0218(5) Uani 1 1 d . . .
H25 H 0.8334 1.064 0.7721 0.026 Uiso 1 1 calc R . .
C26 C 0.75016(19) 0.9160(2) 0.72102(9) 0.0175(5) Uani 1 1 d . . .
H26 H 0.68 0.9625 0.7059 0.021 Uiso 1 1 calc R . .
C27 C 0.63090(18) 0.7787(2) 0.58068(9) 0.0180(5) Uani 1 1 d . . .
C28 C 0.6829(2) 0.8975(2) 0.57271(10) 0.0242(6) Uani 1 1 d . . .
H28 H 0.7296 0.9417 0.6052 0.029 Uiso 1 1 calc R . .
C29 C 0.6662(2) 0.9513(3) 0.51684(11) 0.0333(7) Uani 1 1 d . . .
H29 H 0.7015 1.0326 0.5111 0.04 Uiso 1 1 calc R . .
C30 C 0.5984(2) 0.8870(3) 0.46969(11) 0.0364(7) Uani 1 1 d . . .
H30 H 0.5871 0.9244 0.4316 0.044 Uiso 1 1 calc R . .
C31 C 0.5469(2) 0.7687(3) 0.47738(10) 0.0323(7) Uani 1 1 d . . .
H31 H 0.5009 0.7247 0.4445 0.039 Uiso 1 1 calc R . .
C32 C 0.56199(19) 0.7134(3) 0.53308(9) 0.0247(6) Uani 1 1 d . . .
H32 H 0.5259 0.6324 0.5386 0.03 Uiso 1 1 calc R . .
C14 C 0.51543(17) 0.7301(2) 0.67987(9) 0.0140(5) Uani 1 1 d . . .
H14A H 0.5259 0.6902 0.7193 0.017 Uiso 1 1 calc R . .
H14B H 0.5015 0.8248 0.6839 0.017 Uiso 1 1 calc R . .
C2 C 0.28648(18) 0.4805(2) 0.61075(9) 0.0165(5) Uani 1 1 d . . .
C3 C 0.38086(17) 0.5416(2) 0.64769(9) 0.0156(5) Uani 1 1 d . . .
H3 H 0.4264 0.493 0.6791 0.019 Uiso 1 1 calc R . .
C4 C 0.41024(17) 0.6700(2) 0.64017(9) 0.0133(5) Uani 1 1 d . . .
C5 C 0.34164(18) 0.7414(2) 0.59433(9) 0.0163(5) Uani 1 1 d . . .
H5 H 0.3599 0.8305 0.5889 0.02 Uiso 1 1 calc R . .
C6 C 0.24767(19) 0.6841(2) 0.55695(9) 0.0185(5) Uani 1 1 d . . .
H6 H 0.2021 0.7336 0.5259 0.022 Uiso 1 1 calc R . .
C7 C 0.26148(19) 0.3459(2) 0.62253(10) 0.0196(5) Uani 1 1 d . . .
H7 H 0.3154 0.298 0.6511 0.024 Uiso 1 1 calc R . .
C8 C 0.04913(19) 0.1023(2) 0.59032(10) 0.0189(5) Uani 1 1 d . . .
H10 H 0.1664(19) -0.050(2) 0.6806(10) 0.023 Uiso 1 1 d . . .
H2 H 0.215(2) 0.120(2) 0.6279(10) 0.017(6) Uiso 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 0 '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'
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'
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
C21 P C27 110.90(11) . . ?
C21 P C15 108.51(10) . . ?
C27 P C15 108.23(10) . . ?
C21 P C14 106.85(10) . . ?
C27 P C14 110.05(10) . . ?
C15 P C14 112.31(10) . . ?
C7 N1 N2 115.54(19) . . ?
C8 N2 N1 118.6(2) . . ?
C10 N3 C11 116.0(2) . . ?
O1 C1 C6 117.5(2) . . ?
O1 C1 C2 122.3(2) . . ?
C6 C1 C2 120.2(2) . . ?
C10 C9 C13 118.1(2) . . ?
C10 C9 C8 125.1(2) . . ?
C13 C9 C8 116.8(2) . . ?
N3 C10 C9 124.1(2) . . ?
N3 C11 C12 124.3(2) . . ?
C11 C12 C13 118.6(2) . . ?
C12 C13 C9 118.8(2) . . ?
C16 C15 C20 120.0(2) . . ?
C16 C15 P 119.93(16) . . ?
C20 C15 P 119.91(17) . . ?
C17 C16 C15 119.8(2) . . ?
C16 C17 C18 120.0(2) . . ?
C19 C18 C17 120.4(2) . . ?
C18 C19 C20 120.0(2) . . ?
C19 C20 C15 119.8(2) . . ?
C22 C21 C26 120.2(2) . . ?
C22 C21 P 119.48(17) . . ?
C26 C21 P 120.34(16) . . ?
C23 C22 C21 119.8(2) . . ?
C24 C23 C22 119.8(2) . . ?
C23 C24 C25 121.0(2) . . ?
C24 C25 C26 119.7(2) . . ?
C25 C26 C21 119.5(2) . . ?
C28 C27 C32 120.5(2) . . ?
C28 C27 P 120.82(17) . . ?
C32 C27 P 118.64(18) . . ?
C27 C28 C29 119.5(2) . . ?
C30 C29 C28 120.1(3) . . ?
C29 C30 C31 120.5(2) . . ?
C30 C31 C32 120.3(2) . . ?
C31 C32 C27 119.0(2) . . ?
C4 C14 P 112.46(14) . . ?
C3 C2 C1 118.1(2) . . ?
C3 C2 C7 118.3(2) . . ?
C1 C2 C7 123.5(2) . . ?
C4 C3 C2 122.3(2) . . ?
C3 C4 C5 118.5(2) . . ?
C3 C4 C14 120.28(19) . . ?
C5 C4 C14 121.26(19) . . ?
C6 C5 C4 120.8(2) . . ?
C5 C6 C1 120.2(2) . . ?
N1 C7 C2 121.0(2) . . ?
O2 C8 N2 123.5(2) . . ?
O2 C8 C9 121.9(2) . . ?
N2 C8 C9 114.6(2) . . ?
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
P C21 1.792(2) . ?
P C27 1.800(2) . ?
P C15 1.800(2) . ?
P C14 1.807(2) . ?
O1 C1 1.359(2) . ?
O2 C8 1.221(3) . ?
N1 C7 1.282(3) . ?
N1 N2 1.382(3) . ?
N2 C8 1.359(3) . ?
N3 C10 1.337(3) . ?
N3 C11 1.342(3) . ?
C1 C6 1.389(3) . ?
C1 C2 1.405(3) . ?
C9 C10 1.386(3) . ?
C9 C13 1.389(3) . ?
C9 C8 1.496(3) . ?
C11 C12 1.376(3) . ?
C12 C13 1.378(3) . ?
C15 C16 1.390(3) . ?
C15 C20 1.398(3) . ?
C16 C17 1.384(3) . ?
C17 C18 1.391(3) . ?
C18 C19 1.382(3) . ?
C19 C20 1.387(3) . ?
C21 C22 1.393(3) . ?
C21 C26 1.399(3) . ?
C22 C23 1.387(3) . ?
C23 C24 1.380(3) . ?
C24 C25 1.386(3) . ?
C25 C26 1.390(3) . ?
C27 C28 1.388(3) . ?
C27 C32 1.396(3) . ?
C28 C29 1.389(3) . ?
C29 C30 1.379(4) . ?
C30 C31 1.379(4) . ?
C31 C32 1.392(3) . ?
C14 C4 1.505(3) . ?
C2 C3 1.396(3) . ?
C2 C7 1.445(3) . ?
C3 C4 1.377(3) . ?
C4 C5 1.399(3) . ?
C5 C6 1.380(3) . ?
