# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2024

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_C1
_database_code_depnum_ccdc_archive 'CCDC 2331377'
loop_
_audit_author_name
_audit_author_address
'Davi Back'
;Federal University of Santa Maria
Brazil
;
_audit_update_record             
;
2024-03-27 deposited with the CCDC.	2024-04-17 downloaded from the CCDC.
;

_audit_creation_date             2024-03-22T08:15:11-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_name_systematic        
'{3-[(2-benzoylhydrazono)methyl]-4-hydroxybenzyl}        triphenylphosphonium chloride vanadium (V) dioxido complex'
_chemical_name_common            '[VO2(L1]3H2O'
_chemical_formula_moiety         'C33 H30 N2 O6 P V'
_chemical_formula_sum            'C33 H30 N2 O6 P V'
_chemical_formula_weight         632.5
_chemical_melting_point          455K
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   P-1
_symmetry_space_group_name_Hall  -P1


#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.8606(4)
_cell_length_b                   10.6648(4)
_cell_length_c                   15.2352(6)
_cell_angle_alpha                87.9290(10)
_cell_angle_beta                 89.6510(10)
_cell_angle_gamma                75.6100(10)
_cell_volume                     1550.87(11)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9885
_cell_measurement_theta_min      2.343
_cell_measurement_theta_max      28.595

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       tabular
_exptl_crystal_colour            orange
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.13
_exptl_crystal_density_diffrn    1.354
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             652
_exptl_special_details           
;
 none
;

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    0.418
_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_absorpt_correction_T_min  0.8174
_exptl_absorpt_correction_T_max  0.9076

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_source                   'micro-focus tube'
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  'Montel type 2-dim beam shaping X ray optics'
_diffrn_detector_area_resol_mean 10.4167
_diffrn_measurement_device_type  'Bruker D8 Quest Photon 100 diffractometer'
_diffrn_measurement_method       '2° φ & ω scans'
_diffrn_reflns_av_R_equivalents  0.0295
_diffrn_reflns_av_unetI/netI     0.0236
_diffrn_reflns_number            45636
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         2.34
_diffrn_reflns_theta_max         29.62
_diffrn_reflns_theta_full        29.62
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_reflns_number_total             8713
_reflns_number_gt                7648
_reflns_threshold_expression     >2σ(I)

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       'Bruker Instrument Service v4.2.7'
_computing_cell_refinement       'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_structure_solution    'SHELXL97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Diamond (version 3.2i; Crystal Impact GbR'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION
#----------------------------------------------------------------------------#

_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2σ(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1619P)²+4.3619P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       none
_refine_ls_number_reflns         8713
_refine_ls_number_parameters     388
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0913
_refine_ls_R_factor_gt           0.0836
_refine_ls_wR_factor_ref         0.152
_refine_ls_wR_factor_gt          0.1449
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_restrained_S_all      1.059
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         1.169
_refine_diff_density_min         -1.604
_refine_diff_density_rms         0.17

#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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'
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_
_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
C1 C 0.4304(3) 0.3791(3) 0.54615(19) 0.0143(5) Uani 1 1 d . . .
C2 C 0.5704(3) 0.3156(3) 0.5671(2) 0.0162(5) Uani 1 1 d . . .
C3 C 0.6562(3) 0.2513(3) 0.5000(2) 0.0194(6) Uani 1 1 d . . .
H3 H 0.7509 0.2084 0.5128 0.023 Uiso 1 1 calc R . .
C4 C 0.6053(3) 0.2496(3) 0.4162(2) 0.0196(6) Uani 1 1 d . . .
H4 H 0.6656 0.2058 0.3721 0.024 Uiso 1 1 calc R . .
C5 C 0.4650(3) 0.3119(3) 0.39462(19) 0.0159(5) Uani 1 1 d . . .
C6 C 0.3805(3) 0.3760(3) 0.46014(19) 0.0149(5) Uani 1 1 d . . .
H6 H 0.2861 0.4192 0.4467 0.018 Uiso 1 1 calc R . .
C7 C 0.3381(3) 0.4546(3) 0.60886(19) 0.0153(5) Uani 1 1 d . . .
H7 H 0.2469 0.5 0.5899 0.018 Uiso 1 1 calc R . .
C8 C 0.3232(3) 0.5611(3) 0.81554(19) 0.0166(5) Uani 1 1 d . . .
C9 C 0.2412(3) 0.6568(3) 0.8767(2) 0.0191(6) Uani 1 1 d . . .
C10 C 0.1131(4) 0.7383(4) 0.8516(2) 0.0289(7) Uani 1 1 d . . .
H10 H 0.0771 0.734 0.7944 0.035 Uiso 1 1 calc R . .
C11 C 0.0373(4) 0.8263(4) 0.9102(3) 0.0371(9) Uani 1 1 d . . .
H11 H -0.0503 0.8817 0.893 0.045 Uiso 1 1 calc R . .
C12 C 0.0896(5) 0.8331(4) 0.9934(3) 0.0405(10) Uani 1 1 d . . .
H12 H 0.0358 0.8908 1.034 0.049 Uiso 1 1 calc R . .
C13 C 0.2197(6) 0.7566(4) 1.0181(3) 0.0431(11) Uani 1 1 d . . .
H13 H 0.2573 0.7649 1.0743 0.052 Uiso 1 1 calc R . .
C14 C 0.2953(4) 0.6670(3) 0.9601(2) 0.0306(8) Uani 1 1 d . . .
H14 H 0.3837 0.6129 0.9772 0.037 Uiso 1 1 calc R . .
C15 C 0.4125(3) 0.3160(3) 0.30162(19) 0.0175(5) Uani 1 1 d . . .
H15A H 0.4807 0.3431 0.262 0.021 Uiso 1 1 calc R . .
H15B H 0.3231 0.3832 0.2963 0.021 Uiso 1 1 calc R . .
C16 C 0.5383(3) 0.0383(3) 0.2869(2) 0.0191(6) Uani 1 1 d . . .
C17 C 0.6497(4) 0.0205(4) 0.2275(3) 0.0335(9) Uani 1 1 d . . .
H17 H 0.6407 0.0696 0.1736 0.04 Uiso 1 1 calc R . .
C18 C 0.7737(4) -0.0706(6) 0.2487(4) 0.0535(15) Uani 1 1 d . . .
H18 H 0.8498 -0.0849 0.2086 0.064 Uiso 1 1 calc R . .
C19 C 0.7869(4) -0.1403(4) 0.3275(4) 0.0506(14) Uani 1 1 d . . .
H19 H 0.8715 -0.2033 0.3408 0.061 Uiso 1 1 calc R . .
C20 C 0.6781(4) -0.1194(4) 0.3875(4) 0.0461(13) Uani 1 1 d . . .
H20 H 0.6893 -0.1656 0.4425 0.055 Uiso 1 1 calc R . .
C21 C 0.5523(4) -0.0306(4) 0.3668(3) 0.0325(8) Uani 1 1 d . . .
H21 H 0.4765 -0.0171 0.407 0.039 Uiso 1 1 calc R . .
C22 C 0.2373(3) 0.1255(3) 0.31763(19) 0.0157(5) Uani 1 1 d . . .
C23 C 0.2198(3) 0.0001(3) 0.3121(3) 0.0248(7) Uani 1 1 d . . .
H23 H 0.2884 -0.0645 0.2839 0.03 Uiso 1 1 calc R . .
C24 C 0.1015(4) -0.0294(3) 0.3480(3) 0.0277(7) Uani 1 1 d . . .
H24 H 0.0884 -0.1143 0.3438 0.033 Uiso 1 1 calc R . .
C25 C 0.0018(3) 0.0649(4) 0.3903(2) 0.0278(7) Uani 1 1 d . . .
H25 H -0.0792 0.0442 0.4146 0.033 Uiso 1 1 calc R . .
C26 C 0.0203(4) 0.1889(4) 0.3970(3) 0.0303(8) Uani 1 1 d . . .
H26 H -0.0469 0.2525 0.4269 0.036 Uiso 1 1 calc R . .
C27 C 0.1379(3) 0.2201(3) 0.3598(2) 0.0221(6) Uani 1 1 d . . .
H27 H 0.15 0.3055 0.3631 0.027 Uiso 1 1 calc R . .
C28 C 0.3566(3) 0.1816(3) 0.14745(19) 0.0182(5) Uani 1 1 d . . .
C29 C 0.3544(3) 0.0707(3) 0.1018(2) 0.0212(6) Uani 1 1 d . . .
H29 H 0.3672 -0.0108 0.1321 0.025 Uiso 1 1 calc R . .
C30 C 0.3332(4) 0.0814(4) 0.0109(2) 0.0265(7) Uani 1 1 d . . .
H30 H 0.3293 0.0072 -0.0207 0.032 Uiso 1 1 calc R . .
C31 C 0.3179(5) 0.1995(4) -0.0331(2) 0.0344(8) Uani 1 1 d . . .
H31 H 0.3064 0.2059 -0.0951 0.041 Uiso 1 1 calc R . .
C32 C 0.3193(7) 0.3084(5) 0.0130(3) 0.0525(15) Uani 1 1 d . . .
H32 H 0.3083 0.3893 -0.0179 0.063 Uiso 1 1 calc R . .
C33 C 0.3363(6) 0.3018(4) 0.1039(2) 0.0409(11) Uani 1 1 d . . .
H33 H 0.3342 0.3775 0.1354 0.049 Uiso 1 1 calc R . .
N1 N 0.3728(3) 0.4641(2) 0.69023(17) 0.0159(5) Uani 1 1 d . . .
N2 N 0.2720(3) 0.5524(3) 0.73746(17) 0.0182(5) Uani 1 1 d . . .
O1 O 0.6262(2) 0.3190(2) 0.64519(15) 0.0208(4) Uani 1 1 d . . .
O2 O 0.4455(2) 0.4932(2) 0.84159(14) 0.0197(4) Uani 1 1 d . . .
O3 O 0.5431(3) 0.2279(2) 0.80609(16) 0.0247(5) Uani 1 1 d . . .
O4 O 0.7039(3) 0.3952(2) 0.79349(17) 0.0255(5) Uani 1 1 d . . .
O5 O 1.1000(4) -0.3707(5) 0.3775(3) 0.0647(12) Uani 1 1 d . . .
O6 O 1.0068(5) -0.5019(5) 0.2501(4) 0.0771(15) Uani 1 1 d . . .
P P 0.38422(8) 0.16504(7) 0.26391(5) 0.01387(18) Uani 1 1 d . . .
V V 0.55759(5) 0.36444(5) 0.76180(3) 0.01553(16) Uani 1 1 d . . .
H5A H 1.0902 -0.4373 0.3353 0.05 Uiso 1 1 d D . .
H5B H 1.1943 -0.364 0.3691 0.05 Uiso 1 1 d D . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_geom_special_details            
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes.
;
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
C1 C6 1.407(4) . ?
C1 C2 1.411(4) . ?
C1 C7 1.439(4) . ?
C2 O1 1.319(4) . ?
C2 C3 1.408(4) . ?
C3 C4 1.377(4) . ?
C4 C5 1.413(4) . ?
C5 C6 1.384(4) . ?
C5 C15 1.507(4) . ?
C7 N1 1.302(4) . ?
C8 O2 1.299(4) . ?
C8 N2 1.310(4) . ?
C8 C9 1.487(4) . ?
C9 C10 1.391(5) . ?
C9 C14 1.399(4) . ?
C10 C11 1.393(5) . ?
C11 C12 1.383(6) . ?
C12 C13 1.384(6) . ?
C13 C14 1.397(5) . ?
C15 P 1.814(3) . ?
C16 C21 1.388(5) . ?
C16 C17 1.400(5) . ?
C16 P 1.791(3) . ?
C17 C18 1.392(6) . ?
C18 C19 1.378(9) . ?
C19 C20 1.386(8) . ?
C20 C21 1.391(5) . ?
C22 C27 1.393(4) . ?
C22 C23 1.396(4) . ?
C22 P 1.792(3) . ?
C23 C24 1.386(4) . ?
C24 C25 1.393(5) . ?
C25 C26 1.387(6) . ?
C26 C27 1.395(5) . ?
C28 C33 1.391(5) . ?
C28 C29 1.398(4) . ?
C28 P 1.792(3) . ?
C29 C30 1.399(5) . ?
C30 C31 1.380(6) . ?
C31 C32 1.381(6) . ?
C32 C33 1.394(5) . ?
N1 N2 1.403(3) . ?
N1 V 2.148(3) . ?
O1 V 1.932(2) . ?
O2 V 1.984(2) . ?
O3 V 1.621(2) . ?
O4 V 1.636(2) . ?

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
C6 C1 C2 119.7(3) . . ?
C6 C1 C7 118.2(3) . . ?
C2 C1 C7 122.0(3) . . ?
O1 C2 C3 118.6(3) . . ?
O1 C2 C1 123.1(3) . . ?
C3 C2 C1 118.2(3) . . ?
C4 C3 C2 121.1(3) . . ?
C3 C4 C5 121.2(3) . . ?
C6 C5 C4 117.9(3) . . ?
C6 C5 C15 121.2(3) . . ?
C4 C5 C15 120.8(3) . . ?
C5 C6 C1 121.8(3) . . ?
N1 C7 C1 123.5(3) . . ?
O2 C8 N2 123.2(3) . . ?
O2 C8 C9 117.7(3) . . ?
N2 C8 C9 119.1(3) . . ?
C10 C9 C14 119.4(3) . . ?
C10 C9 C8 121.1(3) . . ?
C14 C9 C8 119.5(3) . . ?
C9 C10 C11 120.1(3) . . ?
C12 C11 C10 120.1(4) . . ?
C11 C12 C13 120.5(4) . . ?
C12 C13 C14 119.6(3) . . ?
C13 C14 C9 120.1(3) . . ?
C5 C15 P 115.5(2) . . ?
C21 C16 C17 120.8(3) . . ?
C21 C16 P 120.1(3) . . ?
C17 C16 P 118.7(3) . . ?
C18 C17 C16 118.8(5) . . ?
C19 C18 C17 120.4(5) . . ?
C18 C19 C20 120.8(4) . . ?
C19 C20 C21 119.7(5) . . ?
C16 C21 C20 119.5(4) . . ?
C27 C22 C23 120.5(3) . . ?
C27 C22 P 120.6(2) . . ?
C23 C22 P 118.8(2) . . ?
C24 C23 C22 119.5(3) . . ?
C23 C24 C25 120.2(3) . . ?
C26 C25 C24 120.3(3) . . ?
C25 C26 C27 119.9(3) . . ?
C22 C27 C26 119.6(3) . . ?
C33 C28 C29 121.0(3) . . ?
C33 C28 P 120.9(2) . . ?
C29 C28 P 118.2(2) . . ?
C28 C29 C30 119.1(3) . . ?
C31 C30 C29 120.2(3) . . ?
C30 C31 C32 120.0(3) . . ?
C31 C32 C33 121.3(4) . . ?
C28 C33 C32 118.4(4) . . ?
C7 N1 N2 113.9(2) . . ?
C7 N1 V 129.9(2) . . ?
N2 N1 V 116.14(18) . . ?
C8 N2 N1 108.2(2) . . ?
C2 O1 V 136.3(2) . . ?
C8 O2 V 118.77(19) . . ?
C16 P C22 109.22(14) . . ?
C16 P C28 109.00(15) . . ?
C22 P C28 110.42(14) . . ?
C16 P C15 108.63(14) . . ?
C22 P C15 111.40(14) . . ?
C28 P C15 108.12(14) . . ?
O3 V O4 109.89(13) . . ?
O3 V O1 103.50(12) . . ?
O4 V O1 93.69(12) . . ?
O3 V O2 102.69(11) . . ?
O4 V O2 91.94(11) . . ?
O1 V O2 149.47(10) . . ?
O3 V N1 112.38(12) . . ?
O4 V N1 137.30(11) . . ?
O1 V N1 82.33(10) . . ?
O2 V N1 73.36(9) . . ?

# END of CIF
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_C2
_database_code_depnum_ccdc_archive 'CCDC 2331378'
loop_
_audit_author_name
_audit_author_address
'Davi Back'
;Federal University of Santa Maria
Brazil
;
_audit_update_record             
;
2024-03-27 deposited with the CCDC.	2024-04-17 downloaded from the CCDC.
;

_audit_creation_date             2024-03-20T17:00:13-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_name_systematic        
'{4-hydroxy-3-[(2-nicotinoylhydrazono)methyl]        benzyl}triphenylphosphonium chloride vanadium (V) dioxo complex'
_chemical_name_common            '[VO2(L2)]CH3OH 4H2O'
_chemical_formula_moiety         'C32 H25 N3 O4 P V, C H4 O, 2(O), 2(H2 O)'
_chemical_formula_sum            'C33 H37 N3 O9 P V'
_chemical_formula_weight         701.57
_chemical_melting_point          456K
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   P-1
_symmetry_space_group_name_Hall  -P1


#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   11.2125(3)
_cell_length_b                   12.2196(4)
_cell_length_c                   14.1895(4)
_cell_angle_alpha                67.9900(10)
_cell_angle_beta                 78.4230(10)
_cell_angle_gamma                65.2980(10)
_cell_volume                     1635.27(8)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9905
_cell_measurement_theta_min      2.2.01
_cell_measurement_theta_max      28.332

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       block
_exptl_crystal_colour            orange
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.15
_exptl_crystal_density_meas      none
_exptl_crystal_density_diffrn    1.425
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             724
_exptl_special_details           
;
 none
;

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    0.411
_exptl_absorpt_correction_type   none
_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_absorpt_correction_T_min  0.9106
_exptl_absorpt_correction_T_max  0.9509

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_source                   'micro-focus tube'
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  'Montel type 2-dim beam shaping X ray optics'
_diffrn_detector_area_resol_mean 10.4167
_diffrn_measurement_device_type  'Bruker D8 Quest Photon 100 diffractometer'
_diffrn_measurement_method       '2° φ & ω scans'
_diffrn_reflns_av_R_equivalents  0.0251
_diffrn_reflns_av_unetI/netI     0.0261
_diffrn_reflns_number            30241
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         1.94
_diffrn_reflns_theta_max         28.34
_diffrn_reflns_theta_full        28.34
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_reflns_number_total             8131
_reflns_number_gt                7055
_reflns_threshold_expression     >2σ(I)

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       'Bruker Instrument Service v4.2.7'
_computing_cell_refinement       'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_structure_solution    'SHELXL97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Diamond (version 3.2i; Crystal Impact GbR'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION
#----------------------------------------------------------------------------#

_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2σ(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0428P)²+1.5938P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       none
_refine_ls_number_reflns         8131
_refine_ls_number_parameters     440
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0478
_refine_ls_R_factor_gt           0.039
_refine_ls_wR_factor_ref         0.0984
_refine_ls_wR_factor_gt          0.0938
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_restrained_S_all      1.027
_refine_ls_shift/su_max          0.014
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.991
_refine_diff_density_min         -0.572
_refine_diff_density_rms         0.062

#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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'
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_
_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 0.83390(3) 0.83034(2) 0.328534(19) 0.01076(7) Uani 1 1 d . . .
P P 0.65304(4) 0.23107(4) 0.74293(3) 0.01164(9) Uani 1 1 d . . .
O1 O 0.79612(14) 0.74891(11) 0.46818(9) 0.0214(3) Uani 1 1 d . . .
O2 O 0.92136(11) 0.83339(10) 0.19242(8) 0.0136(2) Uani 1 1 d . . .
O3 O 0.68747(12) 0.93161(12) 0.29228(9) 0.0221(3) Uani 1 1 d . . .
O4 O 0.91545(12) 0.90262(12) 0.34822(9) 0.0196(3) Uani 1 1 d . . .
O5 O 0.51105(18) 1.18214(18) 0.23960(17) 0.0534(5) Uani 1 1 d . . .
O6 O 0.6319(3) 0.4198(3) -0.0419(2) 0.1034(10) Uani 1 1 d . . .
O7 O 0.6746(2) 0.6428(2) -0.09430(18) 0.0675(6) Uani 1 1 d . . .
O8 O 0.91077(18) 0.62113(15) -0.20800(12) 0.0375(4) Uani 1 1 d . . .
O9 O 0.97491(16) 0.77119(14) -0.40560(14) 0.0334(3) Uani 1 1 d . . .
N1 N 0.88968(13) 0.64295(13) 0.32051(10) 0.0126(3) Uani 1 1 d . . .
N2 N 0.94146(13) 0.62826(13) 0.22487(10) 0.0137(3) Uani 1 1 d . . .
N3 N 1.01335(15) 0.69847(14) -0.09431(11) 0.0214(3) Uani 1 1 d . . .
C14 C 0.79124(15) 0.27374(15) 0.73794(12) 0.0144(3) Uani 1 1 d . . .
H14A H 0.7979 0.2742 0.8063 0.017 Uiso 1 1 calc R . .
H14B H 0.8724 0.2061 0.7231 0.017 Uiso 1 1 calc R . .
C2 C 0.83540(15) 0.53188(15) 0.49290(12) 0.0131(3) Uani 1 1 d . . .
C12 C 1.07150(19) 0.86982(18) -0.10311(14) 0.0242(4) Uani 1 1 d . . .
H12 H 1.1028 0.9356 -0.1428 0.029 Uiso 1 1 calc R . .
C13 C 1.04330(17) 0.84625(16) 0.00065(13) 0.0179(3) Uani 1 1 d . . .
H13 H 1.0556 0.8955 0.0334 0.022 Uiso 1 1 calc R . .
C15 C 0.50195(15) 0.36676(15) 0.73496(12) 0.0134(3) Uani 1 1 d . . .
C16 C 0.47625(17) 0.46454(16) 0.64106(13) 0.0175(3) Uani 1 1 d . . .
H16 H 0.5383 0.4585 0.585 0.021 Uiso 1 1 calc R . .
C17 C 0.35965(18) 0.57036(16) 0.63035(14) 0.0212(4) Uani 1 1 d . . .
H17 H 0.3416 0.6369 0.5667 0.025 Uiso 1 1 calc R . .
C18 C 0.26947(18) 0.57914(17) 0.71243(15) 0.0240(4) Uani 1 1 d . . .
H18 H 0.1889 0.6509 0.7044 0.029 Uiso 1 1 calc R . .
C19 C 0.29609(18) 0.48397(18) 0.80598(15) 0.0254(4) Uani 1 1 d . . .
H19 H 0.2348 0.4918 0.8623 0.03 Uiso 1 1 calc R . .
C20 C 0.41223(17) 0.37684(16) 0.81786(13) 0.0190(3) Uani 1 1 d . . .
H20 H 0.4302 0.3112 0.8819 0.023 Uiso 1 1 calc R . .
C21 C 0.65804(15) 0.10687(15) 0.86220(12) 0.0145(3) Uani 1 1 d . . .
C22 C 0.66141(16) 0.12833(16) 0.95176(12) 0.0176(3) Uani 1 1 d . . .
H22 H 0.6595 0.2079 0.949 0.021 Uiso 1 1 calc R . .
C23 C 0.66765(17) 0.03224(18) 1.04459(13) 0.0208(4) Uani 1 1 d . . .
H23 H 0.6695 0.0461 1.1057 0.025 Uiso 1 1 calc R . .
C24 C 0.67111(16) -0.08383(17) 1.04808(13) 0.0216(4) Uani 1 1 d . . .
H24 H 0.6749 -0.1491 1.1118 0.026 Uiso 1 1 calc R . .
C25 C 0.66907(17) -0.10569(16) 0.95961(14) 0.0208(4) Uani 1 1 d . . .
H25 H 0.6722 -0.1859 0.9629 0.025 Uiso 1 1 calc R . .
C26 C 0.66248(16) -0.01064(16) 0.86598(13) 0.0176(3) Uani 1 1 d . . .
H26 H 0.661 -0.0254 0.8052 0.021 Uiso 1 1 calc R . .
C27 C 0.66402(16) 0.17514(15) 0.64054(12) 0.0140(3) Uani 1 1 d . . .
C28 C 0.54931(16) 0.17577(16) 0.61519(13) 0.0184(3) Uani 1 1 d . . .
H28 H 0.4672 0.2116 0.6482 0.022 Uiso 1 1 calc R . .
C29 C 0.55596(18) 0.12375(18) 0.54159(14) 0.0227(4) Uani 1 1 d . . .
H29 H 0.4786 0.1226 0.525 0.027 Uiso 1 1 calc R . .
C30 C 0.67560(19) 0.07346(17) 0.49230(14) 0.0226(4) Uani 1 1 d . . .
H30 H 0.6798 0.0382 0.4418 0.027 Uiso 1 1 calc R . .
C31 C 0.78970(17) 0.07427(16) 0.51623(13) 0.0204(3) Uani 1 1 d . . .
H31 H 0.8709 0.0411 0.4811 0.025 Uiso 1 1 calc R . .
C32 C 0.78505(16) 0.12343(15) 0.59119(13) 0.0167(3) Uani 1 1 d . . .
H32 H 0.8631 0.1221 0.6089 0.02 Uiso 1 1 calc R . .
C33 C 0.5880(3) 1.2481(2) 0.2362(2) 0.0437(6) Uani 1 1 d . . .
H33A H 0.5426 1.3067 0.2754 0.066 Uiso 1 1 calc R . .
H33B H 0.603 1.2967 0.1653 0.066 Uiso 1 1 calc R . .
H33C H 0.6725 1.1875 0.2654 0.066 Uiso 1 1 calc R . .
C1 C 0.78919(16) 0.63818(15) 0.52655(12) 0.0152(3) Uani 1 1 d . . .
C3 C 0.83522(15) 0.41308(15) 0.56163(12) 0.0135(3) Uani 1 1 d . . .
H3 H 0.8684 0.3412 0.5391 0.016 Uiso 1 1 calc R . .
C4 C 0.78735(15) 0.40044(15) 0.66114(12) 0.0140(3) Uani 1 1 d . . .
C5 C 0.73712(17) 0.50819(16) 0.69266(12) 0.0172(3) Uani 1 1 d . . .
H5 H 0.7021 0.5006 0.7606 0.021 Uiso 1 1 calc R . .
C6 C 0.73740(18) 0.62467(16) 0.62745(12) 0.0187(3) Uani 1 1 d . . .
H6 H 0.7025 0.6962 0.6506 0.022 Uiso 1 1 calc R . .
C7 C 0.88587(15) 0.53918(15) 0.39050(12) 0.0133(3) Uani 1 1 d . . .
H7 H 0.9184 0.4636 0.3729 0.016 Uiso 1 1 calc R . .
C8 C 0.95138(15) 0.73485(15) 0.16437(11) 0.0123(3) Uani 1 1 d . . .
C9 C 0.99686(15) 0.74992(15) 0.05622(12) 0.0136(3) Uani 1 1 d . . .
C10 C 0.98556(16) 0.67709(16) 0.00558(13) 0.0172(3) Uani 1 1 d . . .
H10 H 0.9568 0.6092 0.0437 0.021 Uiso 1 1 calc R . .
C11 C 1.05301(19) 0.79550(18) -0.14713(13) 0.0246(4) Uani 1 1 d . . .
H11 H 1.0691 0.8137 -0.2186 0.03 Uiso 1 1 calc R . .
H1 H 0.569(2) 1.084(2) 0.2674(19) 0.037 Uiso 1 1 d . . .
H1C H 0.956(3) 0.631(2) -0.170(2) 0.037 Uiso 1 1 d . . .
H1D H 0.953(3) 0.549(3) -0.2117(19) 0.037 Uiso 1 1 d . . .
H1A H 0.933(3) 0.745(3) -0.349(2) 0.037 Uiso 1 1 d . . .
H1B H 0.922(3) 0.791(2) -0.448(2) 0.037 Uiso 1 1 d . . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_geom_special_details            
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes.
;
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 1.6296(12) . ?
V O4 1.6298(12) . ?
V O1 1.9062(12) . ?
V O2 1.9773(11) . ?
V N1 2.1489(13) . ?
P C27 1.7875(16) . ?
P C21 1.7923(16) . ?
P C15 1.7946(16) . ?
P C14 1.8116(16) . ?
O1 C1 1.321(2) . ?
O2 C8 1.2994(19) . ?
O5 C33 1.390(3) . ?
N1 C7 1.296(2) . ?
N1 N2 1.4108(18) . ?
N2 C8 1.300(2) . ?
N3 C10 1.337(2) . ?
N3 C11 1.344(2) . ?
C14 C4 1.511(2) . ?
C2 C1 1.410(2) . ?
C2 C3 1.414(2) . ?
C2 C7 1.433(2) . ?
C12 C11 1.376(3) . ?
C12 C13 1.386(2) . ?
C13 C9 1.389(2) . ?
C15 C20 1.393(2) . ?
C15 C16 1.400(2) . ?
C16 C17 1.387(2) . ?
C17 C18 1.386(3) . ?
C18 C19 1.384(3) . ?
C19 C20 1.391(2) . ?
C21 C26 1.397(2) . ?
C21 C22 1.401(2) . ?
C22 C23 1.388(2) . ?
C23 C24 1.385(3) . ?
C24 C25 1.384(3) . ?
C25 C26 1.390(2) . ?
C27 C28 1.400(2) . ?
C27 C32 1.402(2) . ?
C28 C29 1.388(2) . ?
C29 C30 1.387(3) . ?
C30 C31 1.393(3) . ?
C31 C32 1.388(2) . ?
C1 C6 1.408(2) . ?
C3 C4 1.381(2) . ?
C4 C5 1.404(2) . ?
C5 C6 1.378(2) . ?
C8 C9 1.484(2) . ?
C9 C10 1.391(2) . ?

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 110.09(7) . . ?
O3 V O1 100.95(6) . . ?
O4 V O1 96.61(6) . . ?
O3 V O2 98.15(5) . . ?
O4 V O2 93.00(5) . . ?
O1 V O2 154.15(5) . . ?
O3 V N1 116.19(6) . . ?
O4 V N1 133.03(6) . . ?
O1 V N1 82.51(5) . . ?
O2 V N1 73.45(5) . . ?
C27 P C21 109.90(8) . . ?
C27 P C15 108.00(7) . . ?
C21 P C15 110.95(7) . . ?
C27 P C14 111.71(8) . . ?
C21 P C14 106.06(7) . . ?
C15 P C14 110.25(7) . . ?
C1 O1 V 138.21(11) . . ?
C8 O2 V 118.43(10) . . ?
C7 N1 N2 114.01(13) . . ?
C7 N1 V 130.28(11) . . ?
N2 N1 V 115.70(9) . . ?
C8 N2 N1 108.06(12) . . ?
C10 N3 C11 117.77(15) . . ?
C4 C14 P 116.40(11) . . ?
C1 C2 C3 119.86(14) . . ?
C1 C2 C7 121.95(14) . . ?
C3 C2 C7 118.17(14) . . ?
C11 C12 C13 118.26(16) . . ?
C12 C13 C9 119.36(16) . . ?
C20 C15 C16 120.21(15) . . ?
C20 C15 P 122.41(12) . . ?
C16 C15 P 117.38(12) . . ?
C17 C16 C15 119.65(16) . . ?
C18 C17 C16 120.04(16) . . ?
C19 C18 C17 120.39(16) . . ?
C18 C19 C20 120.29(17) . . ?
C19 C20 C15 119.39(16) . . ?
C26 C21 C22 120.37(15) . . ?
C26 C21 P 120.85(13) . . ?
C22 C21 P 118.75(12) . . ?
C23 C22 C21 119.44(16) . . ?
C24 C23 C22 120.02(17) . . ?
C25 C24 C23 120.65(15) . . ?
C24 C25 C26 120.21(16) . . ?
C25 C26 C21 119.30(16) . . ?
C28 C27 C32 120.26(15) . . ?
C28 C27 P 118.16(12) . . ?
C32 C27 P 121.43(12) . . ?
C29 C28 C27 119.73(16) . . ?
C30 C29 C28 119.95(17) . . ?
C29 C30 C31 120.52(17) . . ?
C32 C31 C30 120.17(16) . . ?
C31 C32 C27 119.35(16) . . ?
O1 C1 C6 118.65(15) . . ?
O1 C1 C2 122.62(14) . . ?
C6 C1 C2 118.70(15) . . ?
C4 C3 C2 120.74(15) . . ?
C3 C4 C5 118.81(14) . . ?
C3 C4 C14 122.18(15) . . ?
C5 C4 C14 118.99(14) . . ?
C6 C5 C4 121.56(15) . . ?
C5 C6 C1 120.25(16) . . ?
N1 C7 C2 123.77(14) . . ?
O2 C8 N2 123.63(14) . . ?
O2 C8 C9 116.18(13) . . ?
N2 C8 C9 120.18(14) . . ?
C13 C9 C10 118.16(15) . . ?
C13 C9 C8 119.37(14) . . ?
C10 C9 C8 122.29(15) . . ?
N3 C10 C9 122.90(16) . . ?
N3 C11 C12 123.46(16) . . ?

# END of CIF
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_AHCl
_database_code_depnum_ccdc_archive 'CCDC 2331385'
loop_
_audit_author_name
_audit_author_address
'Davi Back'
;Federal University of Santa Maria
Brazil
;
_audit_update_record             
;
2024-03-27 deposited with the CCDC.	2024-04-17 downloaded from the CCDC.
;

_audit_creation_date             2024-03-19T11:13:48-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_name_systematic        
;
        3-formyl-4-hydroxybenzyl)triphenylphosphonium chloride
;
_chemical_name_common            none
_chemical_formula_moiety         'C26 H22 O2 P, Cl'
_chemical_formula_sum            'C52 H44 Cl2 O4 P2'
_chemical_formula_weight         865.71
_chemical_melting_point          519K
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   P-1
_symmetry_space_group_name_Hall  -P1


#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.7713(5)
_cell_length_b                   13.1128(6)
_cell_length_c                   17.6654(9)
_cell_angle_alpha                105.387(2)
_cell_angle_beta                 92.247(2)
_cell_angle_gamma                90.731(2)
_cell_volume                     2180.01(19)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9860
_cell_measurement_theta_min      2.359
_cell_measurement_theta_max      29.576

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.29
_exptl_crystal_size_min          0.25
_exptl_crystal_density_meas      none
_exptl_crystal_density_diffrn    1.319
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             904
_exptl_special_details           
;
 none
;

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    0.269
_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_absorpt_correction_T_min  0.8483
_exptl_absorpt_correction_T_max  0.9458

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_source                   'micro-focus tube'
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  'Montel type 2-dim beam shaping X ray optics'
_diffrn_detector_area_resol_mean 10.4167
_diffrn_measurement_device_type  'Bruker D8 Quest Photon 100 diffractometer'
_diffrn_measurement_method       '2° φ & ω scans'
_diffrn_reflns_av_R_equivalents  0.0354
_diffrn_reflns_av_unetI/netI     0.0429
_diffrn_reflns_number            43134
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         2.09
_diffrn_reflns_theta_max         29.63
_diffrn_reflns_theta_full        29.63
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_reflns_number_total             12285
_reflns_number_gt                9901
_reflns_threshold_expression     >2σ(I)

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       'Bruker Instrument Service v4.2.7'
_computing_cell_refinement       'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_structure_solution    'SHELXL97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Diamond (version 3.2i; Crystal Impact GbR'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION
#----------------------------------------------------------------------------#

_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2σ(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0487P)²+3.7695P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       none
_refine_ls_number_reflns         12285
_refine_ls_number_parameters     547
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0923
_refine_ls_R_factor_gt           0.076
_refine_ls_wR_factor_ref         0.1452
_refine_ls_wR_factor_gt          0.148
_refine_ls_goodness_of_fit_ref   1.165
_refine_ls_restrained_S_all      1.165
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.117
_refine_diff_density_min         -0.442
_refine_diff_density_rms         0.104

#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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'
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_
_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
C1 C 0.2556(4) 0.3888(3) 0.6518(2) 0.0220(7) Uani 1 1 d . . .
C2 C 0.2356(4) 0.3545(3) 0.5700(2) 0.0199(7) Uani 1 1 d . . .
C3 C 0.3188(4) 0.2767(3) 0.5255(2) 0.0203(7) Uani 1 1 d . . .
H3 H 0.3045 0.2543 0.47 0.024 Uiso 1 1 calc R . .
C4 C 0.4220(4) 0.2319(3) 0.5617(2) 0.0197(7) Uani 1 1 d . . .
C5 C 0.4376(4) 0.2643(3) 0.6439(2) 0.0231(7) Uani 1 1 d . . .
H5 H 0.5057 0.2327 0.6695 0.028 Uiso 1 1 calc R . .
C6 C 0.3565(4) 0.3411(3) 0.6888(2) 0.0245(7) Uani 1 1 d . . .
H6 H 0.369 0.3614 0.7445 0.029 Uiso 1 1 calc R . .
C7 C 0.1257(4) 0.4008(3) 0.5307(2) 0.0260(8) Uani 1 1 d . . .
H7 H 0.0821 0.4618 0.5607 0.031 Uiso 1 1 calc R . .
C8 C 0.5153(4) 0.1500(3) 0.5148(2) 0.0190(6) Uani 1 1 d . . .
H8A H 0.463 0.1059 0.4682 0.023 Uiso 1 1 calc R . .
H8B H 0.5463 0.1032 0.5475 0.023 Uiso 1 1 calc R . .
C9 C 0.6125(4) 0.2707(3) 0.4075(2) 0.0207(7) Uani 1 1 d . . .
C10 C 0.5475(4) 0.3685(3) 0.4253(2) 0.0247(7) Uani 1 1 d . . .
H10 H 0.5341 0.4051 0.4785 0.03 Uiso 1 1 calc R . .
C11 C 0.5027(5) 0.4118(3) 0.3653(2) 0.0299(8) Uani 1 1 d . . .
H11 H 0.4618 0.4792 0.3775 0.036 Uiso 1 1 calc R . .
C12 C 0.5175(5) 0.3571(4) 0.2880(2) 0.0361(10) Uani 1 1 d . . .
H12 H 0.4864 0.3873 0.2472 0.043 Uiso 1 1 calc R . .
C13 C 0.5768(6) 0.2594(4) 0.2690(2) 0.0432(12) Uani 1 1 d . . .
H13 H 0.5854 0.2219 0.2155 0.052 Uiso 1 1 calc R . .
C14 C 0.6242(5) 0.2160(4) 0.3291(2) 0.0365(10) Uani 1 1 d . . .
H14 H 0.6649 0.1484 0.3163 0.044 Uiso 1 1 calc R . .
C15 C 0.7832(4) 0.1072(3) 0.44325(19) 0.0182(6) Uani 1 1 d . . .
C16 C 0.9233(4) 0.1319(3) 0.4522(2) 0.0241(7) Uani 1 1 d . . .
H16 H 0.9546 0.2005 0.4811 0.029 Uiso 1 1 calc R . .
C17 C 1.0173(4) 0.0555(3) 0.4185(2) 0.0280(8) Uani 1 1 d . . .
H17 H 1.1127 0.0721 0.4243 0.034 Uiso 1 1 calc R . .
C18 C 0.9711(4) -0.0445(3) 0.3768(2) 0.0293(8) Uani 1 1 d . . .
H18 H 1.035 -0.0959 0.3531 0.035 Uiso 1 1 calc R . .
C19 C 0.8323(4) -0.0703(3) 0.3692(2) 0.0310(9) Uani 1 1 d . . .
H19 H 0.802 -0.1398 0.3416 0.037 Uiso 1 1 calc R . .
C20 C 0.7366(4) 0.0056(3) 0.4019(2) 0.0263(8) Uani 1 1 d . . .
H20 H 0.6413 -0.0116 0.3962 0.032 Uiso 1 1 calc R . .
C21 C 0.7454(4) 0.3008(3) 0.56637(19) 0.0186(6) Uani 1 1 d . . .
C22 C 0.7707(4) 0.2646(3) 0.6332(2) 0.0255(8) Uani 1 1 d . . .
H22 H 0.7484 0.1934 0.6321 0.031 Uiso 1 1 calc R . .
C23 C 0.8285(5) 0.3329(3) 0.7010(2) 0.0303(8) Uani 1 1 d . . .
H23 H 0.8475 0.3079 0.746 0.036 Uiso 1 1 calc R . .
C24 C 0.8584(4) 0.4362(3) 0.7036(2) 0.0282(8) Uani 1 1 d . . .
H24 H 0.8951 0.483 0.7509 0.034 Uiso 1 1 calc R . .
C25 C 0.8354(4) 0.4727(3) 0.6375(2) 0.0295(8) Uani 1 1 d . . .
H25 H 0.8573 0.5441 0.6393 0.035 Uiso 1 1 calc R . .
C26 C 0.7800(4) 0.4042(3) 0.5684(2) 0.0252(7) Uani 1 1 d . . .
H26 H 0.766 0.4286 0.5226 0.03 Uiso 1 1 calc R . .
C27 C -0.2874(4) 0.1050(3) -0.1308(2) 0.0208(7) Uani 1 1 d . . .
C28 C -0.3033(4) 0.1464(3) -0.04972(19) 0.0185(6) Uani 1 1 d . . .
C29 C -0.2105(4) 0.2240(3) -0.00570(19) 0.0174(6) Uani 1 1 d . . .
H29 H -0.2222 0.2519 0.049 0.021 Uiso 1 1 calc R . .
C30 C -0.1021(3) 0.2611(3) -0.04004(19) 0.0168(6) Uani 1 1 d . . .
C31 C -0.0870(4) 0.2171(3) -0.12111(19) 0.0197(7) Uani 1 1 d . . .
H31 H -0.0128 0.2409 -0.1457 0.024 Uiso 1 1 calc R . .
C32 C -0.1768(4) 0.1406(3) -0.16573(19) 0.0207(7) Uani 1 1 d . . .
H32 H -0.1635 0.112 -0.2202 0.025 Uiso 1 1 calc R . .
C33 C -0.4181(4) 0.1082(3) -0.0116(2) 0.0231(7) Uani 1 1 d . . .
H33 H -0.4784 0.0549 -0.0431 0.028 Uiso 1 1 calc R . .
C34 C -0.0029(3) 0.3466(3) 0.00535(18) 0.0162(6) Uani 1 1 d . . .
H34A H -0.0514 0.3951 0.0481 0.019 Uiso 1 1 calc R . .
H34B H 0.0292 0.3881 -0.0301 0.019 Uiso 1 1 calc R . .
C35 C 0.1027(4) 0.2592(3) 0.13479(19) 0.0200(7) Uani 1 1 d . . .
C36 C 0.1898(5) 0.1934(3) 0.1641(2) 0.0329(9) Uani 1 1 d . . .
H36 H 0.2658 0.1625 0.1353 0.04 Uiso 1 1 calc R . .
C37 C 0.1635(6) 0.1738(4) 0.2360(2) 0.0429(12) Uani 1 1 d . . .
H37 H 0.2213 0.1286 0.2563 0.051 Uiso 1 1 calc R . .
C38 C 0.0535(6) 0.2200(3) 0.2780(2) 0.0402(11) Uani 1 1 d . . .
H38 H 0.0367 0.2064 0.3271 0.048 Uiso 1 1 calc R . .
C39 C -0.0319(5) 0.2853(3) 0.2498(2) 0.0327(9) Uani 1 1 d . . .
H39 H -0.1073 0.3163 0.2791 0.039 Uiso 1 1 calc R . .
C40 C -0.0074(4) 0.3058(3) 0.1779(2) 0.0229(7) Uani 1 1 d . . .
H40 H -0.0655 0.3515 0.1584 0.027 Uiso 1 1 calc R . .
C41 C 0.2771(4) 0.3959(3) 0.07077(18) 0.0176(6) Uani 1 1 d . . .
C42 C 0.4140(4) 0.3670(3) 0.0749(2) 0.0269(8) Uani 1 1 d . . .
H42 H 0.4364 0.2945 0.0648 0.032 Uiso 1 1 calc R . .
C43 C 0.5164(4) 0.4443(4) 0.0937(2) 0.0301(9) Uani 1 1 d . . .
H43 H 0.6095 0.4249 0.096 0.036 Uiso 1 1 calc R . .
C44 C 0.4837(4) 0.5498(3) 0.1090(2) 0.0275(8) Uani 1 1 d . . .
H44 H 0.5546 0.6026 0.1214 0.033 Uiso 1 1 calc R . .
C45 C 0.3479(4) 0.5793(3) 0.1063(2) 0.0273(8) Uani 1 1 d . . .
H45 H 0.3263 0.6521 0.1175 0.033 Uiso 1 1 calc R . .
C46 C 0.2436(4) 0.5025(3) 0.0873(2) 0.0214(7) Uani 1 1 d . . .
H46 H 0.1506 0.5224 0.0857 0.026 Uiso 1 1 calc R . .
C47 C 0.1988(4) 0.1833(3) -0.02639(19) 0.0209(7) Uani 1 1 d . . .
C48 C 0.1505(5) 0.0814(3) -0.0290(2) 0.0292(8) Uani 1 1 d . . .
H48 H 0.1016 0.0691 0.0133 0.035 Uiso 1 1 calc R . .
C49 C 0.1749(6) -0.0016(3) -0.0942(3) 0.0401(11) Uani 1 1 d . . .
H49 H 0.1428 -0.0711 -0.0965 0.048 Uiso 1 1 calc R . .
C50 C 0.2454(6) 0.0167(4) -0.1553(3) 0.0424(12) Uani 1 1 d . . .
H50 H 0.262 -0.0407 -0.1995 0.051 Uiso 1 1 calc R . .
C51 C 0.2925(5) 0.1167(4) -0.1537(2) 0.0367(10) Uani 1 1 d . . .
H51 H 0.3408 0.1282 -0.1964 0.044 Uiso 1 1 calc R . .
C52 C 0.2687(4) 0.2007(3) -0.0889(2) 0.0290(8) Uani 1 1 d . . .
H52 H 0.3003 0.2701 -0.0874 0.035 Uiso 1 1 calc R . .
Cl1 Cl 0.14258(9) 0.44195(7) 0.85477(5) 0.02133(18) Uani 1 1 d . . .
Cl2 Cl -0.36137(10) 0.01218(7) -0.34283(5) 0.0257(2) Uani 1 1 d . . .
O1 O 0.1776(3) 0.4661(2) 0.69298(16) 0.0299(6) Uani 1 1 d . . .
O2 O 0.0882(3) 0.3655(2) 0.46239(17) 0.0322(6) Uani 1 1 d . . .
O3 O -0.3802(3) 0.0320(2) -0.17156(16) 0.0287(6) Uani 1 1 d . . .
O4 O -0.4394(3) 0.1414(2) 0.05795(16) 0.0270(6) Uani 1 1 d . . .
P1 P 0.66419(9) 0.20839(7) 0.48250(5) 0.01694(18) Uani 1 1 d . . .
P2 P 0.14400(9) 0.29551(7) 0.04739(5) 0.01557(17) Uani 1 1 d . . .
H8 H 0.177(5) 0.461(4) 0.748(3) 0.023 Uiso 1 1 d . . .
H9 H -0.371(5) 0.027(4) -0.223(3) 0.023 Uiso 1 1 d . . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_geom_special_details            
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes.
;
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
C1 O1 1.346(4) . ?
C1 C2 1.399(5) . ?
C1 C6 1.404(5) . ?
C2 C3 1.403(5) . ?
C2 C7 1.478(5) . ?
C3 C4 1.391(5) . ?
C4 C5 1.403(5) . ?
C4 C8 1.510(5) . ?
C5 C6 1.384(5) . ?
C7 O2 1.213(5) . ?
C8 P1 1.816(4) . ?
C9 C14 1.390(5) . ?
C9 C10 1.403(5) . ?
C9 P1 1.793(4) . ?
C10 C11 1.388(5) . ?
C11 C12 1.378(6) . ?
C12 C13 1.377(7) . ?
C13 C14 1.400(6) . ?
C15 C16 1.396(5) . ?
C15 C20 1.398(5) . ?
C15 P1 1.791(3) . ?
C16 C17 1.397(5) . ?
C17 C18 1.383(6) . ?
C18 C19 1.385(6) . ?
C19 C20 1.401(5) . ?
C21 C26 1.385(5) . ?
C21 C22 1.400(5) . ?
C21 P1 1.796(3) . ?
C22 C23 1.386(5) . ?
C23 C24 1.371(6) . ?
C24 C25 1.386(6) . ?
C25 C26 1.394(5) . ?
C27 O3 1.349(4) . ?
C27 C32 1.399(5) . ?
C27 C28 1.407(5) . ?
C28 C29 1.402(5) . ?
C28 C33 1.478(5) . ?
C29 C30 1.385(5) . ?
C30 C31 1.409(5) . ?
C30 C34 1.508(5) . ?
C31 C32 1.379(5) . ?
C33 O4 1.217(5) . ?
C34 P2 1.807(3) . ?
C35 C40 1.395(5) . ?
C35 C36 1.399(5) . ?
C35 P2 1.791(3) . ?
C36 C37 1.395(6) . ?
C37 C38 1.383(7) . ?
C38 C39 1.375(7) . ?
C39 C40 1.394(5) . ?
C41 C46 1.397(5) . ?
C41 C42 1.399(5) . ?
C41 P2 1.794(4) . ?
C42 C43 1.382(6) . ?
C43 C44 1.381(6) . ?
C44 C45 1.389(6) . ?
C45 C46 1.390(5) . ?
C47 C52 1.387(5) . ?
C47 C48 1.400(6) . ?
C47 P2 1.791(3) . ?
C48 C49 1.389(5) . ?
C49 C50 1.374(7) . ?
C50 C51 1.377(7) . ?
C51 C52 1.392(6) . ?

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
O1 C1 C2 119.3(3) . . ?
O1 C1 C6 121.7(3) . . ?
C2 C1 C6 119.0(3) . . ?
C1 C2 C3 120.4(3) . . ?
C1 C2 C7 119.5(3) . . ?
C3 C2 C7 120.1(3) . . ?
C4 C3 C2 120.7(3) . . ?
C3 C4 C5 118.2(3) . . ?
C3 C4 C8 121.7(3) . . ?
C5 C4 C8 120.1(3) . . ?
C6 C5 C4 121.8(3) . . ?
C5 C6 C1 119.7(3) . . ?
O2 C7 C2 123.7(4) . . ?
C4 C8 P1 112.8(2) . . ?
C14 C9 C10 118.9(3) . . ?
C14 C9 P1 119.1(3) . . ?
C10 C9 P1 121.7(3) . . ?
C11 C10 C9 120.1(3) . . ?
C12 C11 C10 120.1(4) . . ?
C13 C12 C11 120.8(4) . . ?
C12 C13 C14 119.4(4) . . ?
C9 C14 C13 120.6(4) . . ?
C16 C15 C20 120.3(3) . . ?
C16 C15 P1 119.1(3) . . ?
C20 C15 P1 120.6(3) . . ?
C15 C16 C17 119.9(4) . . ?
C18 C17 C16 119.8(4) . . ?
C17 C18 C19 120.6(4) . . ?
C18 C19 C20 120.4(4) . . ?
C15 C20 C19 119.0(4) . . ?
C26 C21 C22 119.6(3) . . ?
C26 C21 P1 123.7(3) . . ?
C22 C21 P1 116.6(3) . . ?
C23 C22 C21 119.7(4) . . ?
C24 C23 C22 120.5(4) . . ?
C23 C24 C25 120.3(4) . . ?
C24 C25 C26 119.8(4) . . ?
C21 C26 C25 120.0(4) . . ?
O3 C27 C32 122.9(3) . . ?
O3 C27 C28 118.0(3) . . ?
C32 C27 C28 119.1(3) . . ?
C29 C28 C27 119.7(3) . . ?
C29 C28 C33 120.5(3) . . ?
C27 C28 C33 119.9(3) . . ?
C30 C29 C28 121.6(3) . . ?
C29 C30 C31 117.7(3) . . ?
C29 C30 C34 122.8(3) . . ?
C31 C30 C34 119.5(3) . . ?
C32 C31 C30 121.9(3) . . ?
C31 C32 C27 120.0(3) . . ?
O4 C33 C28 123.5(3) . . ?
C30 C34 P2 113.2(2) . . ?
C40 C35 C36 120.2(3) . . ?
C40 C35 P2 119.7(3) . . ?
C36 C35 P2 119.7(3) . . ?
C37 C36 C35 119.1(4) . . ?
C38 C37 C36 120.1(4) . . ?
C39 C38 C37 121.0(4) . . ?
C38 C39 C40 119.7(4) . . ?
C39 C40 C35 119.8(4) . . ?
C46 C41 C42 120.2(3) . . ?
C46 C41 P2 120.0(3) . . ?
C42 C41 P2 119.8(3) . . ?
C43 C42 C41 119.8(4) . . ?
C44 C43 C42 120.1(4) . . ?
C43 C44 C45 120.5(4) . . ?
C44 C45 C46 120.1(4) . . ?
C45 C46 C41 119.2(3) . . ?
C52 C47 C48 120.0(3) . . ?
C52 C47 P2 118.5(3) . . ?
C48 C47 P2 120.4(3) . . ?
C49 C48 C47 119.2(4) . . ?
C50 C49 C48 120.1(4) . . ?
C49 C50 C51 121.2(4) . . ?
C50 C51 C52 119.4(4) . . ?
C47 C52 C51 120.1(4) . . ?
C15 P1 C9 108.97(16) . . ?
C15 P1 C21 108.47(16) . . ?
C9 P1 C21 111.88(17) . . ?
C15 P1 C8 109.59(16) . . ?
C9 P1 C8 109.63(17) . . ?
C21 P1 C8 108.27(16) . . ?
C47 P2 C35 110.96(17) . . ?
C47 P2 C41 109.79(17) . . ?
C35 P2 C41 109.24(16) . . ?
C47 P2 C34 106.76(15) . . ?
C35 P2 C34 111.46(17) . . ?
C41 P2 C34 108.58(16) . . ?

# END of CIF
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_C3
_database_code_depnum_ccdc_archive 'CCDC 2331379'
loop_
_audit_author_name
_audit_author_address
'Davi Back'
;Federal University of Santa Maria
Brazil
;
_audit_update_record             
;
2024-03-27 deposited with the CCDC.	2024-04-17 downloaded from the CCDC.
;

_audit_creation_date             2024-02-02T17:28:45-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_name_systematic        
'4-hydroxy-3-[(2-isonicotinoylhydrazono)methyl]benzyl}        triphenylphosphonium chloride vanadium (V) dioxido complex'
_chemical_name_common            '[VO2(L3)]3.5H2O'
_chemical_formula_moiety         'C65 H66 N6 O15 P2 V2'
_chemical_formula_sum            'C65 H66 N6 O15 P2 V2'
_chemical_formula_weight         1335.06
_chemical_melting_point          547K
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   P-1
_symmetry_space_group_name_Hall  -P1


#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   14.3202(4)
_cell_length_b                   15.0874(5)
_cell_length_c                   16.8813(4)
_cell_angle_alpha                114.3870(10)
_cell_angle_beta                 94.1470(10)
_cell_angle_gamma                99.4190(10)
_cell_volume                     3237.11(16)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9889
_cell_measurement_theta_min      2.527
_cell_measurement_theta_max      27.952

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       block
_exptl_crystal_colour            red
_exptl_crystal_size_max          0.31
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.15
_exptl_crystal_density_meas      none
_exptl_crystal_density_diffrn    1.37
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1372
_exptl_special_details           
;
 none
;

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    0.409
_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_absorpt_correction_T_min  0.8938
_exptl_absorpt_correction_T_max  0.9512

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_source                   'micro-focus tube'
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  'Montel type 2-dim beam shaping X ray optics'
_diffrn_detector_area_resol_mean 10.4167
_diffrn_measurement_device_type  'Bruker D8 Quest Photon 100 diffractometer'
_diffrn_measurement_method       '2° φ & ω scans'
_diffrn_reflns_av_R_equivalents  0.0678
_diffrn_reflns_av_unetI/netI     0.0769
_diffrn_reflns_number            60331
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.03
_diffrn_reflns_theta_max         28.3
_diffrn_reflns_theta_full        28.3
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_reflns_number_total             16017
_reflns_number_gt                10301
_reflns_threshold_expression     >2σ(I)

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       'Bruker Instrument Service v4.2.7'
_computing_cell_refinement       'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_structure_solution    'SHELXL97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Diamond (version 3.2i; Crystal Impact GbR'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION
#----------------------------------------------------------------------------#

_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2σ(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1396P)²+2.5752P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         16017
_refine_ls_number_parameters     813
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.1463
_refine_ls_R_factor_gt           0.1011
_refine_ls_wR_factor_ref         0.1174
_refine_ls_wR_factor_gt          0.1402
_refine_ls_goodness_of_fit_ref   1.03
_refine_ls_restrained_S_all      1.049
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         1.169
_refine_diff_density_min         -1.153
_refine_diff_density_rms         0.15

#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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'
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_
_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
P1 P 0.47216(10) 0.44022(9) 0.74481(8) 0.0191(3) Uani 1 1 d . . .
P2 P 0.80694(10) -0.03254(10) 0.72947(9) 0.0224(3) Uani 1 1 d . . .
V1 V 0.64155(7) 0.19531(7) 0.27692(6) 0.0235(2) Uani 1 1 d . . .
V2 V 0.83999(15) 0.55174(14) 0.89566(8) 0.0804(7) Uani 1 1 d . . .
O1 O 0.6994(3) 0.2869(3) 0.3944(3) 0.0286(9) Uani 1 1 d . . .
O2 O 0.5680(3) 0.1766(3) 0.1657(3) 0.0319(9) Uani 1 1 d . . .
O3 O 0.5992(4) 0.0923(3) 0.2819(3) 0.0377(10) Uani 1 1 d . . .
O4 O 0.7440(4) 0.1903(4) 0.2372(3) 0.0428(11) Uani 1 1 d . . .
O5 O 0.8664(5) 0.4414(4) 0.8018(3) 0.0609(17) Uani 1 1 d . . .
O6 O 0.8409(4) 0.6440(4) 1.0193(3) 0.0506(14) Uani 1 1 d . . .
O7 O 0.9471(7) 0.6363(9) 0.8860(6) 0.134(4) Uani 1 1 d . . .
O8 O 0.7744(9) 0.5921(6) 0.8556(4) 0.132(4) Uani 1 1 d . . .
O9 O 1.0206(9) 0.5161(10) 0.7183(9) 0.171(6) Uani 1 1 d . . .
O10 O 1.1394(11) 0.6508(11) 0.7996(13) 0.217(8) Uani 1 1 d . . .
O11 O 1.0770(8) 0.8151(11) 1.5225(9) 0.148(5) Uani 1 1 d . . .
H11A H 1.07 0.757 1.5187 0.222 Uiso 1 1 calc R . .
O12 O 0.9503(4) 0.9294(5) 1.5199(4) 0.0677(18) Uani 1 1 d . . .
C65 C 1.1726(13) 0.8681(15) 1.5619(9) 0.145(7) Uani 1 1 d . . .
H65A H 1.214 0.8555 1.5164 0.217 Uiso 1 1 calc R . .
H65B H 1.1958 0.8458 1.6052 0.217 Uiso 1 1 calc R . .
H65C H 1.1739 0.9396 1.5914 0.217 Uiso 1 1 calc R . .
O14 O 0.0499(6) 0.1441(10) 0.0654(6) 0.128(4) Uani 1 1 d . . .
O15 O 0.0316(5) 0.0103(8) -0.1108(5) 0.101(3) Uani 1 1 d . . .
O16 O 0.1737(4) -0.0233(4) -0.2157(4) 0.0523(13) Uani 1 1 d . . .
N1 N 0.5307(3) 0.2794(3) 0.3118(3) 0.0216(9) Uani 1 1 d . . .
N2 N 0.4614(3) 0.2647(3) 0.2420(3) 0.0228(9) Uani 1 1 d . . .
N3 N 0.3105(4) 0.1240(4) -0.0755(3) 0.0353(12) Uani 1 1 d . . .
N4 N 0.8817(4) 0.5289(4) 1.0627(3) 0.0304(11) Uani 1 1 d . . .
N5 N 0.8763(3) 0.4766(4) 0.9716(3) 0.0285(10) Uani 1 1 d . . .
N6 N 0.8656(4) 0.8128(4) 1.3467(4) 0.0387(13) Uani 1 1 d . . .
C2 C 0.5756(4) 0.3616(4) 0.4692(3) 0.0199(10) Uani 1 1 d . . .
C11 C 0.3902(4) 0.0904(4) -0.0711(4) 0.0297(12) Uani 1 1 d . . .
H11 H 0.4069 0.0462 -0.1245 0.036 Uiso 1 1 calc R . .
C12 C 0.2884(5) 0.1868(4) 0.0005(4) 0.0312(13) Uani 1 1 d . . .
H12 H 0.2321 0.212 -0.0014 0.037 Uiso 1 1 calc R . .
C13 C 0.3438(4) 0.2169(4) 0.0820(4) 0.0272(12) Uani 1 1 d . . .
H13 H 0.3254 0.2612 0.1344 0.033 Uiso 1 1 calc R . .
C14 C 0.5755(4) 0.5021(4) 0.7180(3) 0.0204(10) Uani 1 1 d . . .
H14A H 0.5626 0.5655 0.7201 0.024 Uiso 1 1 calc R . .
H14B H 0.6305 0.5192 0.7646 0.024 Uiso 1 1 calc R . .
C15 C 0.3684(4) 0.4228(4) 0.6697(3) 0.0239(11) Uani 1 1 d . . .
C16 C 0.3344(4) 0.3311(4) 0.5962(4) 0.0298(12) Uani 1 1 d . . .
H16 H 0.361 0.2752 0.5897 0.036 Uiso 1 1 calc R . .
C17 C 0.2617(5) 0.3228(5) 0.5332(4) 0.0377(15) Uani 1 1 d . . .
H17 H 0.2384 0.2607 0.4834 0.045 Uiso 1 1 calc R . .
C18 C 0.2226(5) 0.4033(6) 0.5418(4) 0.0408(16) Uani 1 1 d . . .
H18 H 0.1734 0.3968 0.4977 0.049 Uiso 1 1 calc R . .
C19 C 0.2553(5) 0.4939(5) 0.6150(4) 0.0368(14) Uani 1 1 d . . .
H19 H 0.2273 0.549 0.6216 0.044 Uiso 1 1 calc R . .
C20 C 0.3290(4) 0.5045(4) 0.6791(4) 0.0281(12) Uani 1 1 d . . .
H20 H 0.3521 0.5668 0.7287 0.034 Uiso 1 1 calc R . .
C21 C 0.4583(4) 0.5187(4) 0.8554(3) 0.0210(10) Uani 1 1 d . . .
C22 C 0.3673(4) 0.5222(4) 0.8795(4) 0.0295(12) Uani 1 1 d . . .
H22 H 0.3119 0.4855 0.8366 0.035 Uiso 1 1 calc R . .
C23 C 0.3577(4) 0.5794(5) 0.9663(4) 0.0329(13) Uani 1 1 d . . .
H23 H 0.2958 0.5824 0.9827 0.04 Uiso 1 1 calc R . .
C24 C 0.4387(5) 0.6321(4) 1.0286(4) 0.0300(13) Uani 1 1 d . . .
H24 H 0.4323 0.6711 1.0879 0.036 Uiso 1 1 calc R . .
C25 C 0.5286(4) 0.6280(4) 1.0049(3) 0.0284(12) Uani 1 1 d . . .
H25 H 0.584 0.6643 1.048 0.034 Uiso 1 1 calc R . .
C26 C 0.5385(4) 0.5708(4) 0.9178(4) 0.0254(11) Uani 1 1 d . . .
H26 H 0.6005 0.5677 0.9017 0.03 Uiso 1 1 calc R . .
C27 C 0.4849(4) 0.3206(4) 0.7380(3) 0.0221(11) Uani 1 1 d . . .
C28 C 0.5701(4) 0.2881(4) 0.7244(4) 0.0273(12) Uani 1 1 d . . .
H28 H 0.6238 0.3286 0.7171 0.033 Uiso 1 1 calc R . .
C29 C 0.5761(5) 0.1950(5) 0.7215(4) 0.0323(13) Uani 1 1 d . . .
H29 H 0.6336 0.1715 0.7109 0.039 Uiso 1 1 calc R . .
C30 C 0.4978(5) 0.1371(4) 0.7342(4) 0.0305(13) Uani 1 1 d . . .
H30 H 0.5024 0.0746 0.7332 0.037 Uiso 1 1 calc R . .
C31 C 0.4129(4) 0.1703(4) 0.7484(4) 0.0285(12) Uani 1 1 d . . .
H31 H 0.3595 0.1301 0.7566 0.034 Uiso 1 1 calc R . .
C32 C 0.4057(4) 0.2616(4) 0.7506(4) 0.0262(11) Uani 1 1 d . . .
H32 H 0.3477 0.2843 0.7604 0.031 Uiso 1 1 calc R . .
C33 C 0.8746(5) 0.3498(5) 0.7871(4) 0.0363(14) Uani 1 1 d . . .
C34 C 0.8889(4) 0.3210(4) 0.8553(4) 0.0270(12) Uani 1 1 d . . .
C35 C 0.9026(4) 0.2247(4) 0.8356(4) 0.0265(12) Uani 1 1 d . . .
H35 H 0.9153 0.2068 0.8825 0.032 Uiso 1 1 calc R . .
C36 C 0.8981(4) 0.1545(4) 0.7492(4) 0.0256(11) Uani 1 1 d . . .
C37 C 0.8831(5) 0.1846(4) 0.6823(4) 0.0315(13) Uani 1 1 d . . .
H37 H 0.8805 0.1383 0.6229 0.038 Uiso 1 1 calc R . .
C38 C 0.8718(6) 0.2795(5) 0.7001(4) 0.0420(16) Uani 1 1 d . . .
H38 H 0.8621 0.2977 0.6531 0.05 Uiso 1 1 calc R . .
C39 C 0.8933(4) 0.3874(4) 0.9454(4) 0.0312(13) Uani 1 1 d . . .
H39 H 0.9097 0.3654 0.9888 0.037 Uiso 1 1 calc R . .
C40 C 0.8612(4) 0.6143(4) 1.0784(4) 0.0280(12) Uani 1 1 d . . .
C41 C 0.8615(4) 0.6832(4) 1.1720(4) 0.0284(12) Uani 1 1 d . . .
C42 C 0.8787(5) 0.6538(5) 1.2377(4) 0.0336(13) Uani 1 1 d . . .
H42 H 0.8891 0.5888 1.2242 0.04 Uiso 1 1 calc R . .
C43 C 0.8805(5) 0.7208(5) 1.3239(4) 0.0377(15) Uani 1 1 d . . .
H43 H 0.8929 0.7005 1.3693 0.045 Uiso 1 1 calc R . .
C44 C 0.8480(4) 0.8407(5) 1.2832(4) 0.0358(14) Uani 1 1 d . . .
H44 H 0.837 0.9058 1.2987 0.043 Uiso 1 1 calc R . .
C45 C 0.8450(5) 0.7785(5) 1.1948(4) 0.0352(14) Uani 1 1 d . . .
H45 H 0.8319 0.8006 1.1507 0.042 Uiso 1 1 calc R . .
C46 C 0.9125(4) 0.0513(4) 0.7296(4) 0.0257(11) Uani 1 1 d . . .
H46A H 0.9645 0.0561 0.7741 0.031 Uiso 1 1 calc R . .
H46B H 0.9335 0.0227 0.6713 0.031 Uiso 1 1 calc R . .
C47 C 0.8369(4) -0.1488(4) 0.7127(3) 0.0252(11) Uani 1 1 d . . .
C48 C 0.9254(5) -0.1686(5) 0.6932(4) 0.0378(15) Uani 1 1 d . . .
H48 H 0.9717 -0.1202 0.6867 0.045 Uiso 1 1 calc R . .
C49 C 0.9472(6) -0.2590(6) 0.6828(5) 0.0476(18) Uani 1 1 d . . .
H49 H 1.0081 -0.2726 0.6694 0.057 Uiso 1 1 calc R . .
C50 C 0.8790(6) -0.3288(5) 0.6922(5) 0.0475(18) Uani 1 1 d . . .
H50 H 0.8939 -0.3899 0.6869 0.057 Uiso 1 1 calc R . .
C51 C 0.7892(6) -0.3105(5) 0.7094(4) 0.0412(16) Uani 1 1 d . . .
H51 H 0.7422 -0.36 0.7137 0.049 Uiso 1 1 calc R . .
C52 C 0.7679(5) -0.2204(4) 0.7203(4) 0.0342(14) Uani 1 1 d . . .
H52 H 0.7066 -0.2074 0.7328 0.041 Uiso 1 1 calc R . .
C53 C 0.7659(4) 0.0194(4) 0.8336(4) 0.0241(11) Uani 1 1 d . . .
C54 C 0.7987(4) -0.0034(5) 0.9012(4) 0.0293(12) Uani 1 1 d . . .
H54 H 0.8378 -0.0511 0.8906 0.035 Uiso 1 1 calc R . .
C55 C 0.7740(5) 0.0439(5) 0.9838(4) 0.0351(14) Uani 1 1 d . . .
H55 H 0.7975 0.0294 1.0303 0.042 Uiso 1 1 calc R . .
C56 C 0.7155(5) 0.1122(5) 0.9998(4) 0.0383(15) Uani 1 1 d . . .
H56 H 0.6983 0.1437 1.0566 0.046 Uiso 1 1 calc R . .
C57 C 0.6822(5) 0.1343(5) 0.9318(4) 0.0334(13) Uani 1 1 d . . .
H57 H 0.6419 0.1809 0.9424 0.04 Uiso 1 1 calc R . .
C58 C 0.7071(4) 0.0891(4) 0.8499(4) 0.0278(12) Uani 1 1 d . . .
H58 H 0.6846 0.1049 0.804 0.033 Uiso 1 1 calc R . .
C59 C 0.7130(4) -0.0527(4) 0.6437(4) 0.0251(11) Uani 1 1 d . . .
C60 C 0.7365(5) -0.0456(5) 0.5668(4) 0.0333(13) Uani 1 1 d . . .
H60 H 0.8017 -0.0279 0.5613 0.04 Uiso 1 1 calc R . .
C61 C 0.6644(5) -0.0645(5) 0.4988(4) 0.0381(15) Uani 1 1 d . . .
H61 H 0.6802 -0.0586 0.4473 0.046 Uiso 1 1 calc R . .
C62 C 0.5694(5) -0.0920(4) 0.5060(4) 0.0345(14) Uani 1 1 d . . .
H62 H 0.5203 -0.1045 0.4594 0.041 Uiso 1 1 calc R . .
C63 C 0.5457(4) -0.1013(4) 0.5806(4) 0.0334(13) Uani 1 1 d . . .
H63 H 0.4804 -0.1218 0.5844 0.04 Uiso 1 1 calc R . .
C64 C 0.6162(4) -0.0809(4) 0.6497(4) 0.0274(12) Uani 1 1 d . . .
H64 H 0.5994 -0.0861 0.7013 0.033 Uiso 1 1 calc R . .
C3 C 0.5461(4) 0.4161(4) 0.5499(3) 0.0214(10) Uani 1 1 d . . .
H3 H 0.4851 0.4333 0.55 0.026 Uiso 1 1 calc R . .
C1 C 0.6671(4) 0.3362(4) 0.4680(4) 0.0239(11) Uani 1 1 d . . .
C4 C 0.6053(4) 0.4452(4) 0.6297(3) 0.0204(10) Uani 1 1 d . . .
C5 C 0.6959(4) 0.4215(4) 0.6273(4) 0.0234(11) Uani 1 1 d . . .
H5 H 0.7371 0.4414 0.6811 0.028 Uiso 1 1 calc R . .
C6 C 0.7270(4) 0.3696(4) 0.5485(4) 0.0274(12) Uani 1 1 d . . .
H6 H 0.7897 0.3566 0.5491 0.033 Uiso 1 1 calc R . .
C7 C 0.5127(4) 0.3344(4) 0.3891(3) 0.0199(10) Uani 1 1 d . . .
H7 H 0.4549 0.3579 0.3927 0.024 Uiso 1 1 calc R . .
C8 C 0.4894(4) 0.2083(4) 0.1687(4) 0.0240(11) Uani 1 1 d . . .
C9 C 0.4266(4) 0.1806(4) 0.0849(3) 0.0247(11) Uani 1 1 d . . .
C10 C 0.4498(4) 0.1156(4) 0.0058(4) 0.0275(12) Uani 1 1 d . . .
H10 H 0.5058 0.0893 0.0052 0.033 Uiso 1 1 calc R . .
H10B H 1.1943 0.6507 0.8504 0.05 Uiso 1 1 d D . .
H10A H 1.12 0.7001 0.8243 0.05 Uiso 1 1 d D . .
H12B H 0.9827 0.9853 1.4957 0.05 Uiso 1 1 d D . .
H12A H 0.993 0.8932 1.5409 0.05 Uiso 1 1 d D . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_geom_special_details            
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes.
;
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
P1 C15 1.792(6) . ?
P1 C21 1.798(5) . ?
P1 C27 1.801(5) . ?
P1 C14 1.805(5) . ?
P2 C47 1.787(6) . ?
P2 C53 1.793(5) . ?
P2 C59 1.794(6) . ?
P2 C46 1.804(6) . ?
V1 O3 1.611(4) . ?
V1 O4 1.657(5) . ?
V1 O1 1.911(4) . ?
V1 O2 1.974(4) . ?
V1 N1 2.157(4) . ?
V2 O8 1.465(7) . ?
V2 O5 1.881(5) . ?
V2 O7 1.891(10) . ?
V2 O6 1.971(5) . ?
V2 N5 2.120(5) . ?
O1 C1 1.320(6) . ?
O2 C8 1.289(7) . ?
O5 C33 1.327(8) . ?
O6 C40 1.283(8) . ?
O11 C65 1.424(19) . ?
N1 C7 1.296(6) . ?
N1 N2 1.403(6) . ?
N2 C8 1.315(7) . ?
N3 C11 1.332(8) . ?
N3 C12 1.340(8) . ?
N4 C40 1.293(8) . ?
N4 N5 1.398(6) . ?
N5 C39 1.304(8) . ?
N6 C44 1.326(9) . ?
N6 C43 1.338(9) . ?
C2 C3 1.408(7) . ?
C2 C1 1.423(8) . ?
C2 C7 1.433(7) . ?
C11 C10 1.373(8) . ?
C12 C13 1.392(8) . ?
C13 C9 1.391(8) . ?
C14 C4 1.516(7) . ?
C15 C20 1.393(8) . ?
C15 C16 1.402(8) . ?
C16 C17 1.385(9) . ?
C17 C18 1.378(10) . ?
C18 C19 1.388(10) . ?
C19 C20 1.395(8) . ?
C21 C26 1.376(8) . ?
C21 C22 1.395(8) . ?
C22 C23 1.390(8) . ?
C23 C24 1.384(9) . ?
C24 C25 1.379(9) . ?
C25 C26 1.396(7) . ?
C27 C28 1.386(8) . ?
C27 C32 1.409(8) . ?
C28 C29 1.402(8) . ?
C29 C30 1.391(9) . ?
C30 C31 1.389(9) . ?
C31 C32 1.384(8) . ?
C33 C34 1.401(9) . ?
C33 C38 1.405(8) . ?
C34 C35 1.402(8) . ?
C34 C39 1.424(8) . ?
C35 C36 1.394(7) . ?
C36 C37 1.395(8) . ?
C36 C46 1.506(8) . ?
C37 C38 1.376(9) . ?
C40 C41 1.489(8) . ?
C41 C42 1.376(9) . ?
C41 C45 1.393(9) . ?
C42 C43 1.383(8) . ?
C44 C45 1.389(9) . ?
C47 C48 1.381(8) . ?
C47 C52 1.394(8) . ?
C48 C49 1.393(9) . ?
C49 C50 1.383(11) . ?
C50 C51 1.384(11) . ?
C51 C52 1.383(9) . ?
C53 C54 1.393(8) . ?
C53 C58 1.404(8) . ?
C54 C55 1.383(8) . ?
C55 C56 1.386(9) . ?
C56 C57 1.394(9) . ?
C57 C58 1.371(8) . ?
C59 C64 1.405(8) . ?
C59 C60 1.407(8) . ?
C60 C61 1.388(9) . ?
C61 C62 1.385(9) . ?
C62 C63 1.384(9) . ?
C63 C64 1.382(8) . ?
C3 C4 1.398(7) . ?
C1 C6 1.400(8) . ?
C4 C5 1.400(8) . ?
C5 C6 1.387(7) . ?
C8 C9 1.480(8) . ?
C9 C10 1.394(7) . ?

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
C15 P1 C21 110.0(3) . . ?
C15 P1 C27 108.8(3) . . ?
C21 P1 C27 109.1(2) . . ?
C15 P1 C14 109.0(2) . . ?
C21 P1 C14 107.8(2) . . ?
C27 P1 C14 112.2(3) . . ?
C47 P2 C53 109.1(3) . . ?
C47 P2 C59 109.4(3) . . ?
C53 P2 C59 109.1(3) . . ?
C47 P2 C46 108.9(3) . . ?
C53 P2 C46 109.4(3) . . ?
C59 P2 C46 110.9(3) . . ?
O3 V1 O4 110.4(2) . . ?
O3 V1 O1 105.7(2) . . ?
O4 V1 O1 94.8(2) . . ?
O3 V1 O2 101.7(2) . . ?
O4 V1 O2 93.5(2) . . ?
O1 V1 O2 146.44(18) . . ?
O3 V1 N1 104.4(2) . . ?
O4 V1 N1 144.6(2) . . ?
O1 V1 N1 81.47(17) . . ?
O2 V1 N1 73.14(16) . . ?
O8 V2 O5 105.7(3) . . ?
O8 V2 O7 91.0(6) . . ?
O5 V2 O7 90.7(4) . . ?
O8 V2 O6 97.1(3) . . ?
O5 V2 O6 156.9(2) . . ?
O7 V2 O6 92.1(3) . . ?
O8 V2 N5 154.3(5) . . ?
O5 V2 N5 83.8(2) . . ?
O7 V2 N5 113.1(4) . . ?
O6 V2 N5 74.02(19) . . ?
C1 O1 V1 135.1(4) . . ?
C8 O2 V1 118.5(3) . . ?
C33 O5 V2 136.2(4) . . ?
C40 O6 V2 117.4(4) . . ?
C7 N1 N2 114.1(4) . . ?
C7 N1 V1 129.4(4) . . ?
N2 N1 V1 116.0(3) . . ?
C8 N2 N1 107.1(4) . . ?
C11 N3 C12 117.1(5) . . ?
C40 N4 N5 107.7(5) . . ?
C39 N5 N4 114.8(5) . . ?
C39 N5 V2 129.1(4) . . ?
N4 N5 V2 116.1(4) . . ?
C44 N6 C43 118.1(6) . . ?
C3 C2 C1 120.2(5) . . ?
C3 C2 C7 118.7(5) . . ?
C1 C2 C7 121.1(5) . . ?
N3 C11 C10 124.2(5) . . ?
N3 C12 C13 123.3(6) . . ?
C9 C13 C12 118.5(5) . . ?
C4 C14 P1 116.8(4) . . ?
C20 C15 C16 120.1(5) . . ?
C20 C15 P1 119.2(4) . . ?
C16 C15 P1 120.2(4) . . ?
C17 C16 C15 119.3(6) . . ?
C18 C17 C16 120.9(6) . . ?
C17 C18 C19 119.9(6) . . ?
C18 C19 C20 120.3(6) . . ?
C15 C20 C19 119.4(6) . . ?
C26 C21 C22 119.9(5) . . ?
C26 C21 P1 119.3(4) . . ?
C22 C21 P1 120.6(4) . . ?
C23 C22 C21 120.1(5) . . ?
C24 C23 C22 119.7(5) . . ?
C25 C24 C23 120.3(5) . . ?
C24 C25 C26 120.1(5) . . ?
C21 C26 C25 119.9(5) . . ?
C28 C27 C32 120.4(5) . . ?
C28 C27 P1 122.1(4) . . ?
C32 C27 P1 117.5(4) . . ?
C27 C28 C29 119.4(6) . . ?
C30 C29 C28 120.1(6) . . ?
C31 C30 C29 120.3(5) . . ?
C32 C31 C30 120.2(5) . . ?
C31 C32 C27 119.7(5) . . ?
O5 C33 C34 122.5(5) . . ?
O5 C33 C38 118.9(6) . . ?
C34 C33 C38 118.5(6) . . ?
C33 C34 C35 119.7(5) . . ?
C33 C34 C39 122.4(6) . . ?
C35 C34 C39 117.9(5) . . ?
C36 C35 C34 121.7(5) . . ?
C35 C36 C37 117.6(5) . . ?
C35 C36 C46 120.8(5) . . ?
C37 C36 C46 121.6(5) . . ?
C38 C37 C36 121.8(5) . . ?
C37 C38 C33 120.7(6) . . ?
N5 C39 C34 123.6(6) . . ?
O6 C40 N4 124.8(5) . . ?
O6 C40 C41 117.9(5) . . ?
N4 C40 C41 117.3(5) . . ?
C42 C41 C45 118.7(6) . . ?
C42 C41 C40 120.4(5) . . ?
C45 C41 C40 120.8(6) . . ?
C41 C42 C43 118.5(6) . . ?
N6 C43 C42 123.3(6) . . ?
N6 C44 C45 122.7(6) . . ?
C44 C45 C41 118.7(6) . . ?
C36 C46 P2 114.1(4) . . ?
C48 C47 C52 120.0(6) . . ?
C48 C47 P2 122.0(5) . . ?
C52 C47 P2 118.0(4) . . ?
C47 C48 C49 120.4(6) . . ?
C50 C49 C48 119.2(7) . . ?
C49 C50 C51 120.7(6) . . ?
C52 C51 C50 120.1(7) . . ?
C51 C52 C47 119.6(6) . . ?
C54 C53 C58 119.7(5) . . ?
C54 C53 P2 119.6(4) . . ?
C58 C53 P2 120.5(4) . . ?
C55 C54 C53 119.5(6) . . ?
C54 C55 C56 120.9(6) . . ?
C55 C56 C57 119.4(6) . . ?
C58 C57 C56 120.4(6) . . ?
C57 C58 C53 120.1(6) . . ?
C64 C59 C60 119.1(5) . . ?
C64 C59 P2 121.2(4) . . ?
C60 C59 P2 119.6(4) . . ?
C61 C60 C59 119.9(6) . . ?
C62 C61 C60 120.2(6) . . ?
C63 C62 C61 120.3(6) . . ?
C64 C63 C62 120.4(6) . . ?
C63 C64 C59 120.0(5) . . ?
C4 C3 C2 120.8(5) . . ?
O1 C1 C6 118.9(5) . . ?
O1 C1 C2 122.9(5) . . ?
C6 C1 C2 118.2(5) . . ?
C3 C4 C5 118.3(5) . . ?
C3 C4 C14 122.5(5) . . ?
C5 C4 C14 119.2(5) . . ?
C6 C5 C4 121.7(5) . . ?
C5 C6 C1 120.8(5) . . ?
N1 C7 C2 123.4(5) . . ?
O2 C8 N2 124.1(5) . . ?
O2 C8 C9 118.4(5) . . ?
N2 C8 C9 117.5(5) . . ?
C13 C9 C10 118.2(5) . . ?
C13 C9 C8 122.1(5) . . ?
C10 C9 C8 119.7(5) . . ?
C11 C10 C9 118.7(6) . . ?

# END of CIF
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_H2L2Cl
_database_code_depnum_ccdc_archive 'CCDC 2331386'
loop_
_audit_author_name
_audit_author_address
'Davi Back'
;Federal University of Santa Maria
Brazil
;
_audit_update_record             
;
2024-03-27 deposited with the CCDC.	2024-04-17 downloaded from the CCDC.
;
_audit_creation_date             2024-03-19T12:33:03-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_name_systematic        
'{4-hydroxy-3-[(2-nicotinoylhydrazono)methyl]benzyl}        triphenylphosphonium chloride'
_chemical_name_common            '[H2L2]Cl'
_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          522K
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   P21/c
_symmetry_space_group_name_Hall  -P2ybc


#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

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'

_cell_length_a                   11.6944(5)
_cell_length_b                   10.2221(4)
_cell_length_c                   23.3093(8)
_cell_angle_alpha                90
_cell_angle_beta                 102.2020(10)
_cell_angle_gamma                90
_cell_volume                     2723.47(18)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    6085
_cell_measurement_theta_min      2.241
_cell_measurement_theta_max      27.899

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.04
_exptl_crystal_density_meas      none
_exptl_crystal_density_diffrn    1.346
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1152
_exptl_special_details           
;
 none
;

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    0.235
_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_absorpt_correction_T_min  0.7121
_exptl_absorpt_correction_T_max  0.7457

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_source                   'micro-focus tube'
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  'Montel type 2-dim beam shaping X ray optics'
_diffrn_detector_area_resol_mean 10.4167
_diffrn_measurement_device_type  'Bruker D8 Quest Photon 100 diffractometer'
_diffrn_measurement_method       '2° φ & ω scans'
_diffrn_reflns_av_R_equivalents  0.1037
_diffrn_reflns_av_unetI/netI     0.09
_diffrn_reflns_number            36928
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_theta_min         2.18
_diffrn_reflns_theta_max         28.36
_diffrn_reflns_theta_full        28.36
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_reflns_number_total             6805
_reflns_number_gt                4430
_reflns_threshold_expression     >2σ(I)

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       'Bruker Instrument Service v4.2.7'
_computing_cell_refinement       'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_structure_solution    'SHELXL97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Diamond (version 3.2i; Crystal Impact GbR'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION
#----------------------------------------------------------------------------#

_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2σ(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0352P)²+1.6291P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       none
_refine_ls_number_reflns         6805
_refine_ls_number_parameters     360
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1123
_refine_ls_R_factor_gt           0.0571
_refine_ls_wR_factor_ref         0.1078
_refine_ls_wR_factor_gt          0.0934
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_restrained_S_all      1.027
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.315
_refine_diff_density_min         -0.345
_refine_diff_density_rms         0.07

#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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_
_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 . . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_geom_special_details            
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes.
;
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) . ?

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) . . ?

# END of CIF
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_C4
_database_code_depnum_ccdc_archive 'CCDC 2331380'
loop_
_audit_author_name
_audit_author_address
'Davi Back'
;Federal University of Santa Maria
Brazil
;
_audit_update_record             
;
2024-03-27 deposited with the CCDC.	2024-04-17 downloaded from the CCDC.
;

_audit_creation_date             2024-02-02T18:00:13-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_name_systematic        
'4-hydroxy-3-{[2-(3-hydroxy-2-naphthoyl)hydrazono]methyl}benzyl}triphenylphosphonium chloride vanadium (V) dioxido complex'
_chemical_name_common            '[VO2(HL4)]2CH3OH'
_chemical_formula_moiety         'C37 H28 N2 O5 P V, 2(C H4 O)'
_chemical_formula_sum            'C39 H36 N2 O7 P V'
_chemical_formula_weight         726.61
_chemical_melting_point          451K
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   P-1
_symmetry_space_group_name_Hall  -P1


#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   10.8358(5)
_cell_length_b                   11.2449(4)
_cell_length_c                   14.9567(8)
_cell_angle_alpha                77.0930(10)
_cell_angle_beta                 83.962(2)
_cell_angle_gamma                72.1210(10)
_cell_volume                     1689.29(13)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9943
_cell_measurement_theta_min      2.375
_cell_measurement_theta_max      28.596

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       tabular
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.29
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.09
_exptl_crystal_density_diffrn    1.428
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             756
_exptl_special_details           
;
 none
;

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    0.396
_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_absorpt_correction_T_min  0.8837
_exptl_absorpt_correction_T_max  0.9552

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_source                   'micro-focus tube'
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  'Montel type 2-dim beam shaping X ray optics'
_diffrn_detector_area_resol_mean 10.4167
_diffrn_measurement_device_type  'Bruker D8 Quest Photon 100 diffractometer'
_diffrn_measurement_method       '2° φ & ω scans'
_diffrn_reflns_av_R_equivalents  0.0578
_diffrn_reflns_av_unetI/netI     0.045
_diffrn_reflns_number            54534
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         1.94
_diffrn_reflns_theta_max         28.73
_diffrn_reflns_theta_full        28.73
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_reflns_number_total             8758
_reflns_number_gt                6755
_reflns_threshold_expression     >2σ(I)

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       'Bruker Instrument Service v4.2.7'
_computing_cell_refinement       'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_structure_solution    'SHELXL97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Diamond (version 3.2i; Crystal Impact GbR'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION
#----------------------------------------------------------------------------#

_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2σ(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0442P)²+1.9604P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       none
_refine_ls_number_reflns         8758
_refine_ls_number_parameters     459
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.071
_refine_ls_R_factor_gt           0.0467
_refine_ls_wR_factor_ref         0.1141
_refine_ls_wR_factor_gt          0.1042
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_restrained_S_all      1.026
_refine_ls_shift/su_max          0.014
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.122
_refine_diff_density_min         -0.352
_refine_diff_density_rms         0.071

#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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'
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_
_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 0.43659(3) 0.50973(3) 0.27272(2) 0.01355(9) Uani 1 1 d . . .
P P 0.44590(5) 0.01036(5) 0.76029(3) 0.01368(11) Uani 1 1 d . . .
O1 O 0.33775(14) 0.44075(15) 0.37464(10) 0.0231(3) Uani 1 1 d . . .
O2 O 0.59277(14) 0.55008(13) 0.20739(9) 0.0181(3) Uani 1 1 d . . .
O3 O 0.94892(14) 0.44439(14) 0.33845(10) 0.0195(3) Uani 1 1 d . . .
H3A H 0.880(3) 0.433(2) 0.3590(9) 0.029 Uiso 1 1 calc R . .
O4 O 0.40843(16) 0.43862(15) 0.19780(11) 0.0256(3) Uani 1 1 d . . .
O5 O 0.34301(14) 0.65788(14) 0.25765(10) 0.0225(3) Uani 1 1 d . . .
O6 O 0.0938(2) 0.76413(19) 0.32005(16) 0.0513(6) Uani 1 1 d . . .
H6A H 0.196(4) 0.720(3) 0.2948(13) 0.077 Uiso 1 1 calc R . .
O7 O -0.10127(18) 0.86333(18) 0.19190(14) 0.0380(4) Uani 1 1 d . . .
H7 H -0.048(2) 0.820(3) 0.241(2) 0.057 Uiso 1 1 calc R . .
N1 N 0.59038(16) 0.42425(15) 0.36639(11) 0.0138(3) Uani 1 1 d . . .
N2 N 0.71126(16) 0.43891(15) 0.33348(11) 0.0154(3) Uani 1 1 d . . .
C1 C 0.3544(2) 0.38054(18) 0.46040(13) 0.0159(4) Uani 1 1 d . . .
C2 C 0.47612(19) 0.33922(18) 0.50073(13) 0.0147(4) Uani 1 1 d . . .
C11 C 0.1962(2) -0.1021(2) 0.58553(16) 0.0248(5) Uani 1 1 d . . .
H11 H 0.142 -0.1229 0.5492 0.03 Uiso 1 1 calc R . .
C12 C 0.2836(2) -0.0369(2) 0.54353(15) 0.0215(4) Uani 1 1 d . . .
H12 H 0.2898 -0.0137 0.4785 0.026 Uiso 1 1 calc R . .
C13 C 0.3618(2) -0.00568(19) 0.59630(14) 0.0179(4) Uani 1 1 d . . .
H13 H 0.4229 0.0374 0.5676 0.021 Uiso 1 1 calc R . .
C14 C 0.4259(2) -0.0595(2) 0.87894(13) 0.0174(4) Uani 1 1 d . . .
C15 C 0.4832(2) -0.1909(2) 0.90894(15) 0.0220(4) Uani 1 1 d . . .
H15 H 0.5366 -0.2405 0.8679 0.026 Uiso 1 1 calc R . .
C16 C 0.4610(2) -0.2477(2) 0.99932(15) 0.0260(5) Uani 1 1 d . . .
H16 H 0.4994 -0.3366 1.0203 0.031 Uiso 1 1 calc R . .
C17 C 0.3829(2) -0.1749(2) 1.05902(15) 0.0279(5) Uani 1 1 d . . .
H17 H 0.3673 -0.2144 1.1205 0.033 Uiso 1 1 calc R . .
C18 C 0.3278(2) -0.0452(2) 1.02954(15) 0.0281(5) Uani 1 1 d . . .
H18 H 0.2756 0.0041 1.0711 0.034 Uiso 1 1 calc R . .
C19 C 0.3484(2) 0.0132(2) 0.93951(14) 0.0230(5) Uani 1 1 d . . .
H19 H 0.3099 0.1023 0.9193 0.028 Uiso 1 1 calc R . .
C20 C 0.61214(19) -0.04874(18) 0.72285(13) 0.0146(4) Uani 1 1 d . . .
C21 C 0.6504(2) -0.16662(18) 0.69532(14) 0.0172(4) Uani 1 1 d . . .
H21 H 0.588 -0.2095 0.693 0.021 Uiso 1 1 calc R . .
C22 C 0.7789(2) -0.2200(2) 0.67168(14) 0.0199(4) Uani 1 1 d . . .
H22 H 0.8055 -0.3007 0.6544 0.024 Uiso 1 1 calc R . .
C23 C 0.8689(2) -0.1561(2) 0.67318(15) 0.0214(4) Uani 1 1 d . . .
H23 H 0.957 -0.1927 0.6558 0.026 Uiso 1 1 calc R . .
C24 C 0.8322(2) -0.0390(2) 0.69984(15) 0.0207(4) Uani 1 1 d . . .
H24 H 0.8948 0.0044 0.7001 0.025 Uiso 1 1 calc R . .
C25 C 0.7037(2) 0.01453(19) 0.72605(13) 0.0164(4) Uani 1 1 d . . .
H25 H 0.6783 0.0934 0.746 0.02 Uiso 1 1 calc R . .
C26 C 0.58846(19) 0.36439(18) 0.45106(13) 0.0147(4) Uani 1 1 d . . .
H26 H 0.6674 0.3351 0.4824 0.018 Uiso 1 1 calc R . .
C27 C 0.70123(19) 0.50714(18) 0.24951(13) 0.0145(4) Uani 1 1 d . . .
C28 C 0.81827(19) 0.53678(18) 0.20242(13) 0.0150(4) Uani 1 1 d . . .
C29 C 0.93758(19) 0.50381(18) 0.24824(13) 0.0157(4) Uani 1 1 d . . .
C30 C 1.0444(2) 0.53183(19) 0.20124(14) 0.0181(4) Uani 1 1 d . . .
H30 H 1.123 0.5101 0.2321 0.022 Uiso 1 1 calc R . .
C31 C 1.0391(2) 0.59247(18) 0.10772(14) 0.0178(4) Uani 1 1 d . . .
C32 C 1.1503(2) 0.6189(2) 0.05718(15) 0.0229(5) Uani 1 1 d . . .
H32 H 1.2304 0.595 0.0865 0.028 Uiso 1 1 calc R . .
C33 C 1.1419(2) 0.6783(2) -0.03321(16) 0.0261(5) Uani 1 1 d . . .
H33 H 1.2165 0.6953 -0.0662 0.031 Uiso 1 1 calc R . .
C34 C 1.0236(2) 0.7147(2) -0.07843(15) 0.0251(5) Uani 1 1 d . . .
H34 H 1.0192 0.7563 -0.1412 0.03 Uiso 1 1 calc R . .
C35 C 0.9159(2) 0.6901(2) -0.03210(15) 0.0219(4) Uani 1 1 d . . .
H35 H 0.8369 0.7146 -0.063 0.026 Uiso 1 1 calc R . .
C36 C 0.9207(2) 0.62822(19) 0.06201(14) 0.0179(4) Uani 1 1 d . . .
C37 C 0.8123(2) 0.59881(18) 0.11138(14) 0.0170(4) Uani 1 1 d . . .
H37 H 0.7328 0.6222 0.0813 0.02 Uiso 1 1 calc R . .
C38 C 0.0725(3) 0.6984(3) 0.4095(2) 0.0481(8) Uani 1 1 d . . .
H38A H 0.0517 0.6207 0.4062 0.072 Uiso 1 1 calc R . .
H38B H 0 0.7533 0.4402 0.072 Uiso 1 1 calc R . .
H38C H 0.1509 0.6757 0.4444 0.072 Uiso 1 1 calc R . .
C39 C -0.0306(3) 0.9235(3) 0.1198(2) 0.0437(7) Uani 1 1 d . . .
H39A H -0.0606 0.9226 0.0605 0.066 Uiso 1 1 calc R . .
H39B H 0.0621 0.8774 0.1239 0.066 Uiso 1 1 calc R . .
H39C H -0.0446 1.0119 0.1255 0.066 Uiso 1 1 calc R . .
C3 C 0.48830(19) 0.27527(18) 0.59321(13) 0.0151(4) Uani 1 1 d . . .
H3 H 0.5707 0.2485 0.6198 0.018 Uiso 1 1 calc R . .
C4 C 0.3834(2) 0.25069(18) 0.64600(13) 0.0154(4) Uani 1 1 d . . .
C5 C 0.2622(2) 0.29255(19) 0.60565(14) 0.0180(4) Uani 1 1 d . . .
H5 H 0.1889 0.2767 0.6413 0.022 Uiso 1 1 calc R . .
C6 C 0.2469(2) 0.35611(19) 0.51550(14) 0.0188(4) Uani 1 1 d . . .
H6 H 0.1636 0.3838 0.4901 0.023 Uiso 1 1 calc R . .
C7 C 0.3948(2) 0.18235(18) 0.74544(13) 0.0166(4) Uani 1 1 d . . .
H7A H 0.3097 0.2094 0.778 0.02 Uiso 1 1 calc R . .
H7B H 0.458 0.2084 0.7741 0.02 Uiso 1 1 calc R . .
C8 C 0.35057(19) -0.03785(18) 0.69218(13) 0.0152(4) Uani 1 1 d . . .
C9 C 0.2636(2) -0.1045(2) 0.73420(15) 0.0201(4) Uani 1 1 d . . .
H9 H 0.2565 -0.1273 0.7992 0.024 Uiso 1 1 calc R . .
C10 C 0.1877(2) -0.1371(2) 0.68028(16) 0.0247(5) Uani 1 1 d . . .
H10 H 0.1294 -0.1838 0.7085 0.03 Uiso 1 1 calc R . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_geom_special_details            
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes.
;
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 O4 1.6157(16) . ?
V O5 1.6423(15) . ?
V O1 1.9263(14) . ?
V O2 1.9875(14) . ?
V N1 2.1377(17) . ?
P C8 1.792(2) . ?
P C14 1.793(2) . ?
P C20 1.794(2) . ?
P C7 1.809(2) . ?
O1 C1 1.312(2) . ?
O2 C27 1.297(2) . ?
O3 C29 1.365(2) . ?
O6 C38 1.410(4) . ?
O7 C39 1.423(3) . ?
N1 C26 1.296(2) . ?
N1 N2 1.395(2) . ?
N2 C27 1.313(2) . ?
C1 C2 1.409(3) . ?
C1 C6 1.416(3) . ?
C2 C3 1.408(3) . ?
C2 C26 1.429(3) . ?
C11 C10 1.385(3) . ?
C11 C12 1.388(3) . ?
C12 C13 1.382(3) . ?
C13 C8 1.400(3) . ?
C14 C19 1.395(3) . ?
C14 C15 1.403(3) . ?
C15 C16 1.390(3) . ?
C16 C17 1.388(3) . ?
C17 C18 1.382(3) . ?
C18 C19 1.388(3) . ?
C20 C25 1.397(3) . ?
C20 C21 1.403(3) . ?
C21 C22 1.379(3) . ?
C22 C23 1.382(3) . ?
C23 C24 1.390(3) . ?
C24 C25 1.390(3) . ?
C27 C28 1.477(3) . ?
C28 C37 1.383(3) . ?
C28 C29 1.434(3) . ?
C29 C30 1.374(3) . ?
C30 C31 1.411(3) . ?
C31 C36 1.421(3) . ?
C31 C32 1.428(3) . ?
C32 C33 1.366(3) . ?
C33 C34 1.416(3) . ?
C34 C35 1.364(3) . ?
C35 C36 1.423(3) . ?
C36 C37 1.408(3) . ?
C3 C4 1.378(3) . ?
C4 C5 1.404(3) . ?
C4 C7 1.513(3) . ?
C5 C6 1.378(3) . ?
C8 C9 1.394(3) . ?
C9 C10 1.385(3) . ?

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
O4 V O5 110.45(8) . . ?
O4 V O1 97.87(7) . . ?
O5 V O1 97.03(7) . . ?
O4 V O2 96.25(7) . . ?
O5 V O2 95.94(7) . . ?
O1 V O2 156.12(6) . . ?
O4 V N1 122.98(8) . . ?
O5 V N1 126.22(7) . . ?
O1 V N1 82.26(6) . . ?
O2 V N1 73.91(6) . . ?
C8 P C14 109.62(9) . . ?
C8 P C20 106.86(9) . . ?
C14 P C20 109.39(9) . . ?
C8 P C7 109.87(9) . . ?
C14 P C7 109.49(9) . . ?
C20 P C7 111.57(9) . . ?
C1 O1 V 138.66(13) . . ?
C27 O2 V 118.44(12) . . ?
C26 N1 N2 114.06(16) . . ?
C26 N1 V 130.11(14) . . ?
N2 N1 V 115.77(11) . . ?
C27 N2 N1 109.36(16) . . ?
O1 C1 C2 122.44(18) . . ?
O1 C1 C6 119.49(18) . . ?
C2 C1 C6 118.07(18) . . ?
C3 C2 C1 120.01(18) . . ?
C3 C2 C26 118.31(18) . . ?
C1 C2 C26 121.65(17) . . ?
C10 C11 C12 120.2(2) . . ?
C13 C12 C11 120.0(2) . . ?
C12 C13 C8 119.76(19) . . ?
C19 C14 C15 120.19(19) . . ?
C19 C14 P 120.87(16) . . ?
C15 C14 P 118.83(16) . . ?
C16 C15 C14 119.3(2) . . ?
C17 C16 C15 120.2(2) . . ?
C18 C17 C16 120.4(2) . . ?
C17 C18 C19 120.4(2) . . ?
C18 C19 C14 119.6(2) . . ?
C25 C20 C21 120.18(18) . . ?
C25 C20 P 122.13(15) . . ?
C21 C20 P 117.56(15) . . ?
C22 C21 C20 119.71(19) . . ?
C21 C22 C23 120.02(19) . . ?
C22 C23 C24 120.9(2) . . ?
C25 C24 C23 119.8(2) . . ?
C24 C25 C20 119.41(19) . . ?
N1 C26 C2 124.71(18) . . ?
O2 C27 N2 122.50(18) . . ?
O2 C27 C28 119.31(17) . . ?
N2 C27 C28 118.18(17) . . ?
C37 C28 C29 119.01(18) . . ?
C37 C28 C27 118.87(18) . . ?
C29 C28 C27 122.12(17) . . ?
O3 C29 C30 118.24(18) . . ?
O3 C29 C28 121.74(17) . . ?
C30 C29 C28 120.02(18) . . ?
C29 C30 C31 120.94(19) . . ?
C30 C31 C36 119.62(18) . . ?
C30 C31 C32 121.65(19) . . ?
C36 C31 C32 118.73(19) . . ?
C33 C32 C31 120.3(2) . . ?
C32 C33 C34 120.9(2) . . ?
C35 C34 C33 120.2(2) . . ?
C34 C35 C36 120.6(2) . . ?
C37 C36 C31 118.55(18) . . ?
C37 C36 C35 122.15(19) . . ?
C31 C36 C35 119.29(19) . . ?
C28 C37 C36 121.81(19) . . ?
C4 C3 C2 121.50(19) . . ?
C3 C4 C5 118.30(18) . . ?
C3 C4 C7 122.12(18) . . ?
C5 C4 C7 119.57(18) . . ?
C6 C5 C4 121.57(19) . . ?
C5 C6 C1 120.54(19) . . ?
C4 C7 P 113.47(14) . . ?
C9 C8 C13 120.10(19) . . ?
C9 C8 P 120.32(16) . . ?
C13 C8 P 119.56(15) . . ?
C10 C9 C8 119.4(2) . . ?
C11 C10 C9 120.5(2) . . ?

# END of CIF
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_C5
_database_code_depnum_ccdc_archive 'CCDC 2331383'
loop_
_audit_author_name
_audit_author_address
'Davi Back'
;Federal University of Santa Maria
Brazil
;
_audit_update_record             
;
2024-03-27 deposited with the CCDC.	2024-04-17 downloaded from the CCDC.
;

_audit_creation_date             2024-02-02T15:09:37-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_name_systematic        
'3-{[2-(4-fluorobenzoyl)hydrazono]methyl}-4-hydroxybenzyl}        triphenylphosphonium chloride vanadium (V) dioxido complex'
_chemical_name_common            '[VO2(L50]CH3OH H2O'
_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          448K
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   P-1
_symmetry_space_group_name_Hall  -P1

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.9185(5)
_cell_length_b                   10.6629(4)
_cell_length_c                   15.2191(8)
_cell_angle_alpha                88.136(2)
_cell_angle_beta                 88.887(2)
_cell_angle_gamma                75.909(2)
_cell_volume                     1560.20(13)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9905
_cell_measurement_theta_min      2.501
_cell_measurement_theta_max      28.273

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       tabular
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.11
_exptl_crystal_density_meas      none
_exptl_crystal_density_diffrn    1.415
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             688
_exptl_special_details           
;
 none
;

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    0.424
_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_absorpt_correction_T_min  0.6744
_exptl_absorpt_correction_T_max  0.7457

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_source                   'micro-focus tube'
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  'Montel type 2-dim beam shaping X ray optics'
_diffrn_detector_area_resol_mean 10.4167
_diffrn_measurement_device_type  'Bruker D8 Quest Photon 100 diffractometer'
_diffrn_measurement_method       '2° φ & ω scans'
_diffrn_reflns_av_R_equivalents  0.0378
_diffrn_reflns_av_unetI/netI     0.0383
_diffrn_reflns_number            31886
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         1.97
_diffrn_reflns_theta_max         28.31
_diffrn_reflns_theta_full        28.31
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_reflns_number_total             7748
_reflns_number_gt                6277
_reflns_threshold_expression     >2σ(I)

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       'Bruker Instrument Service v4.2.7'
_computing_cell_refinement       'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_structure_solution    'SHELXL97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Diamond (version 3.2i; Crystal Impact GbR'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION
#----------------------------------------------------------------------------#

_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2σ(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0047P)²+3.3149P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       none
_refine_ls_number_reflns         7748
_refine_ls_number_parameters     408
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0803
_refine_ls_R_factor_gt           0.0627
_refine_ls_wR_factor_ref         0.1935
_refine_ls_wR_factor_gt          0.1816
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_restrained_S_all      1.063
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.842
_refine_diff_density_min         -0.842
_refine_diff_density_rms         0.121

#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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_
_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 . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_geom_special_details            
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes.
;
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) . ?

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) . . ?

# END of CIF
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_H2L3Cl
_database_code_depnum_ccdc_archive 'CCDC 2331387'
loop_
_audit_author_name
_audit_author_address
'Davi Back'
;Federal University of Santa Maria
Brazil
;
_audit_update_record             
;
2024-03-27 deposited with the CCDC.	2024-04-17 downloaded from the CCDC.
;

_audit_creation_date             2024-02-02T18:22:22-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_name_systematic        
'4-hydroxy-3-[(2-isonicotinoylhydrazono)methyl]benzyl}        triphenylphosphonium chloride'
_chemical_name_common            ([H2L3]Cl)
_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          547K
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   P21/c
_symmetry_space_group_name_Hall  -P2ybc


#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

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'

_cell_length_a                   11.5892(4)
_cell_length_b                   10.1708(4)
_cell_length_c                   23.3468(8)
_cell_angle_alpha                90
_cell_angle_beta                 101.7700(10)
_cell_angle_gamma                90
_cell_volume                     2694.06(17)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    7059
_cell_measurement_theta_min      2.681
_cell_measurement_theta_max      28.068

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.27
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.1
_exptl_crystal_density_meas      none
_exptl_crystal_density_diffrn    1.361
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1152
_exptl_special_details           
;
 none
;

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    0.237
_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_absorpt_correction_T_min  0.9488
_exptl_absorpt_correction_T_max  0.9867

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_source                   'micro-focus tube'
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  'Montel type 2-dim beam shaping X ray optics'
_diffrn_detector_area_resol_mean 10.4167
_diffrn_measurement_device_type  'Bruker D8 Quest Photon 100 diffractometer'
_diffrn_measurement_method       '2° φ & ω scans'
_diffrn_reflns_av_R_equivalents  0.0656
_diffrn_reflns_av_unetI/netI     0.0691
_diffrn_reflns_number            27628
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_theta_min         2.19
_diffrn_reflns_theta_max         28.33
_diffrn_reflns_theta_full        28.33
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_reflns_number_total             6718
_reflns_number_gt                4724
_reflns_threshold_expression     >2σ(I)

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       'Bruker Instrument Service v4.2.7'
_computing_cell_refinement       'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_structure_solution    'SHELXL97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Diamond (version 3.2i; Crystal Impact GbR'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION
#----------------------------------------------------------------------------#

_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2σ(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0408P)²+1.9797P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_number_reflns         6718
_refine_ls_number_parameters     358
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0924
_refine_ls_R_factor_gt           0.0511
_refine_ls_wR_factor_ref         0.1115
_refine_ls_wR_factor_gt          0.0979
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_restrained_S_all      1.022
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.431
_refine_diff_density_min         -0.359
_refine_diff_density_rms         0.069

#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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_
_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 0.41774(5) 0.94543(5) 0.67908(2) 0.02019(13) Uani 1 1 d . . .
P P 0.64768(4) 0.31236(5) 0.65463(2) 0.01319(12) Uani 1 1 d . . .
O1 O 0.12035(13) 0.49284(16) 0.51920(6) 0.0240(4) Uani 1 1 d . . .
O2 O -0.04494(13) 0.86440(16) 0.55412(7) 0.0252(4) Uani 1 1 d . . .
N1 N 0.16022(15) 0.72005(17) 0.58184(7) 0.0199(4) Uani 1 1 d . . .
N2 N 0.15075(16) 0.85122(18) 0.59620(8) 0.0201(4) Uani 1 1 d . . .
N3 N 0.04538(16) 1.31193(19) 0.64410(8) 0.0235(4) Uani 1 1 d . . .
C1 C 0.21448(17) 0.4466(2) 0.55856(8) 0.0175(4) Uani 1 1 d . . .
C9 C 0.04889(17) 1.0517(2) 0.60487(8) 0.0168(4) Uani 1 1 d . . .
C10 C -0.02329(18) 1.1455(2) 0.57246(9) 0.0197(5) Uani 1 1 d . . .
H10 H -0.074 1.1225 0.5365 0.024 Uiso 1 1 calc R . .
C11 C -0.02037(19) 1.2730(2) 0.59318(9) 0.0223(5) Uani 1 1 d . . .
H11 H -0.0681 1.3367 0.5697 0.027 Uiso 1 1 calc R . .
C12 C 0.1127(2) 1.2195(2) 0.67491(9) 0.0247(5) Uani 1 1 d . . .
H12 H 0.1599 1.2444 0.7115 0.03 Uiso 1 1 calc R . .
C13 C 0.11901(19) 1.0907(2) 0.65758(9) 0.0207(5) Uani 1 1 d . . .
H13 H 0.1701 1.03 0.6812 0.025 Uiso 1 1 calc R . .
C14 C 0.51164(16) 0.2871(2) 0.67970(8) 0.0142(4) Uani 1 1 d . . .
H14A H 0.5001 0.1917 0.6847 0.017 Uiso 1 1 calc R . .
H14B H 0.518 0.3295 0.7184 0.017 Uiso 1 1 calc R . .
C15 C 0.63474(17) 0.2384(2) 0.58370(8) 0.0158(4) Uani 1 1 d . . .
C16 C 0.56353(18) 0.2991(2) 0.53525(9) 0.0221(5) Uani 1 1 d . . .
H16 H 0.5264 0.3808 0.5396 0.026 Uiso 1 1 calc R . .
C17 C 0.54765(19) 0.2392(3) 0.48098(9) 0.0276(6) Uani 1 1 d . . .
H17 H 0.4999 0.2803 0.4479 0.033 Uiso 1 1 calc R . .
C18 C 0.6011(2) 0.1196(3) 0.47456(10) 0.0301(6) Uani 1 1 d . . .
H18 H 0.5889 0.0785 0.4373 0.036 Uiso 1 1 calc R . .
C19 C 0.6720(2) 0.0602(2) 0.52230(9) 0.0283(5) Uani 1 1 d . . .
H19 H 0.709 -0.0214 0.5177 0.034 Uiso 1 1 calc R . .
C20 C 0.68918(19) 0.1193(2) 0.57703(9) 0.0211(5) Uani 1 1 d . . .
H20 H 0.7381 0.0784 0.6098 0.025 Uiso 1 1 calc R . .
C21 C 0.76154(17) 0.2362(2) 0.70795(8) 0.0163(4) Uani 1 1 d . . .
C22 C 0.74466(19) 0.1089(2) 0.72669(9) 0.0213(5) Uani 1 1 d . . .
H22 H 0.6753 0.0613 0.7101 0.026 Uiso 1 1 calc R . .
C23 C 0.8303(2) 0.0525(2) 0.76980(9) 0.0255(5) Uani 1 1 d . . .
H23 H 0.8201 -0.0348 0.7824 0.031 Uiso 1 1 calc R . .
C24 C 0.9306(2) 0.1224(3) 0.79470(9) 0.0280(6) Uani 1 1 d . . .
H24 H 0.9886 0.083 0.8244 0.034 Uiso 1 1 calc R . .
C25 C 0.94657(19) 0.2488(3) 0.77652(9) 0.0271(5) Uani 1 1 d . . .
H25 H 1.0153 0.2965 0.7939 0.032 Uiso 1 1 calc R . .
C26 C 0.86240(18) 0.3070(2) 0.73268(9) 0.0196(5) Uani 1 1 d . . .
H26 H 0.8736 0.3938 0.7198 0.023 Uiso 1 1 calc R . .
C27 C 0.68085(17) 0.4837(2) 0.64894(8) 0.0152(4) Uani 1 1 d . . .
C28 C 0.65169(17) 0.5738(2) 0.68882(9) 0.0186(5) Uani 1 1 d . . .
H28 H 0.6144 0.5448 0.7192 0.022 Uiso 1 1 calc R . .
C29 C 0.67750(19) 0.7061(2) 0.68370(10) 0.0237(5) Uani 1 1 d . . .
H29 H 0.6537 0.7685 0.7093 0.028 Uiso 1 1 calc R . .
C30 C 0.7378(2) 0.7473(2) 0.64142(10) 0.0274(5) Uani 1 1 d . . .
H30 H 0.7564 0.8378 0.6385 0.033 Uiso 1 1 calc R . .
C31 C 0.77108(19) 0.6576(2) 0.60348(10) 0.0256(5) Uani 1 1 d . . .
H31 H 0.8148 0.686 0.5755 0.031 Uiso 1 1 calc R . .
C32 C 0.74097(18) 0.5262(2) 0.60605(9) 0.0200(5) Uani 1 1 d . . .
H32 H 0.761 0.4652 0.5788 0.024 Uiso 1 1 calc R . .
C2 C 0.28008(17) 0.5275(2) 0.60193(9) 0.0163(4) Uani 1 1 d . . .
C3 C 0.37508(17) 0.4725(2) 0.64114(8) 0.0161(4) Uani 1 1 d . . .
H3 H 0.42 0.5264 0.6707 0.019 Uiso 1 1 calc R . .
C4 C 0.40540(16) 0.3419(2) 0.63800(8) 0.0140(4) Uani 1 1 d . . .
C5 C 0.33799(17) 0.2627(2) 0.59478(8) 0.0161(4) Uani 1 1 d . . .
H5 H 0.3573 0.1724 0.5924 0.019 Uiso 1 1 calc R . .
C6 C 0.24318(18) 0.3147(2) 0.55531(8) 0.0178(4) Uani 1 1 d . . .
H6 H 0.1979 0.2601 0.5261 0.021 Uiso 1 1 calc R . .
C7 C 0.25444(18) 0.6650(2) 0.61014(9) 0.0191(5) Uani 1 1 d . . .
H7 H 0.3089 0.7158 0.6372 0.023 Uiso 1 1 calc R . .
C8 C 0.04529(18) 0.9139(2) 0.58254(9) 0.0183(4) Uani 1 1 d . . .
H2 H 0.105(2) 0.577(3) 0.5325(10) 0.028 Uiso 1 1 d . . .
H1 H 0.210(2) 0.887(2) 0.6172(10) 0.028 Uiso 1 1 d . . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_geom_special_details            
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes.
;
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 1.7948(19) . ?
P C27 1.795(2) . ?
P C15 1.7968(19) . ?
P C14 1.809(2) . ?
O1 C1 1.359(2) . ?
O2 C8 1.226(2) . ?
N1 C7 1.284(3) . ?
N1 N2 1.385(2) . ?
N2 C8 1.357(3) . ?
N3 C12 1.335(3) . ?
N3 C11 1.335(3) . ?
C1 C6 1.388(3) . ?
C1 C2 1.402(3) . ?
C9 C13 1.387(3) . ?
C9 C10 1.387(3) . ?
C9 C8 1.493(3) . ?
C10 C11 1.381(3) . ?
C12 C13 1.378(3) . ?
C14 C4 1.512(3) . ?
C15 C20 1.389(3) . ?
C15 C16 1.400(3) . ?
C16 C17 1.384(3) . ?
C17 C18 1.387(4) . ?
C18 C19 1.382(3) . ?
C19 C20 1.389(3) . ?
C21 C22 1.393(3) . ?
C21 C26 1.394(3) . ?
C22 C23 1.385(3) . ?
C23 C24 1.385(3) . ?
C24 C25 1.378(3) . ?
C25 C26 1.394(3) . ?
C27 C28 1.396(3) . ?
C27 C32 1.400(3) . ?
C28 C29 1.389(3) . ?
C29 C30 1.386(3) . ?
C30 C31 1.381(3) . ?
C31 C32 1.386(3) . ?
C2 C3 1.397(3) . ?
C2 C7 1.451(3) . ?
C3 C4 1.380(3) . ?
C4 C5 1.398(3) . ?
C5 C6 1.387(3) . ?

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 109.41(10) . . ?
C21 P C15 111.71(10) . . ?
C27 P C15 108.48(9) . . ?
C21 P C14 106.27(9) . . ?
C27 P C14 112.07(10) . . ?
C15 P C14 108.93(9) . . ?
C7 N1 N2 113.35(18) . . ?
C8 N2 N1 120.49(18) . . ?
C12 N3 C11 115.8(2) . . ?
O1 C1 C6 117.76(19) . . ?
O1 C1 C2 121.83(19) . . ?
C6 C1 C2 120.40(18) . . ?
C13 C9 C10 117.8(2) . . ?
C13 C9 C8 123.22(19) . . ?
C10 C9 C8 118.98(18) . . ?
C11 C10 C9 119.05(19) . . ?
N3 C11 C10 124.0(2) . . ?
N3 C12 C13 124.9(2) . . ?
C12 C13 C9 118.4(2) . . ?
C4 C14 P 112.85(13) . . ?
C20 C15 C16 120.01(19) . . ?
C20 C15 P 120.92(15) . . ?
C16 C15 P 118.99(17) . . ?
C17 C16 C15 119.5(2) . . ?
C16 C17 C18 120.4(2) . . ?
C19 C18 C17 120.1(2) . . ?
C18 C19 C20 120.2(2) . . ?
C19 C20 C15 119.8(2) . . ?
C22 C21 C26 120.65(19) . . ?
C22 C21 P 119.25(16) . . ?
C26 C21 P 119.98(16) . . ?
C23 C22 C21 119.1(2) . . ?
C22 C23 C24 120.6(2) . . ?
C25 C24 C23 120.2(2) . . ?
C24 C25 C26 120.3(2) . . ?
C21 C26 C25 119.1(2) . . ?
C28 C27 C32 119.9(2) . . ?
C28 C27 P 120.22(16) . . ?
C32 C27 P 119.84(16) . . ?
C29 C28 C27 119.5(2) . . ?
C28 C29 C30 120.2(2) . . ?
C31 C30 C29 120.3(2) . . ?
C30 C31 C32 120.3(2) . . ?
C31 C32 C27 119.7(2) . . ?
C3 C2 C1 118.48(19) . . ?
C3 C2 C7 117.05(18) . . ?
C1 C2 C7 124.45(18) . . ?
C4 C3 C2 121.72(19) . . ?
C3 C4 C5 118.82(18) . . ?
C3 C4 C14 120.24(18) . . ?
C5 C4 C14 120.93(18) . . ?
C6 C5 C4 120.68(19) . . ?
C1 C6 C5 119.90(19) . . ?
N1 C7 C2 121.87(19) . . ?
O2 C8 N2 124.2(2) . . ?
O2 C8 C9 122.29(19) . . ?
N2 C8 C9 113.52(18) . . ?

# END of CIF
