# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2016

####################################################################### 
# 
# 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_sd21
_database_code_depnum_ccdc_archive 'CCDC 1482859'
_audit_update_record             
;
2016-09-29 deposited with the CCDC.
2016-10-17 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
'oxovanadium {(Z)-2-hydroxy-N-((E)-(2-oxidonaphthalen-1-yl)methylene)benzohydrazonate}ethanoate'
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C20 H17 N2 O5 V'
_chemical_formula_sum            'C20 H17 N2 O5 V'
_chemical_formula_weight         416.30

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
V V 0.3005 0.5294 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 21/c'
_symmetry_Int_Tables_number      14

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                   18.249(3)
_cell_length_b                   5.9376(11)
_cell_length_c                   18.227(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 110.346(9)
_cell_angle_gamma                90.00
_cell_volume                     1851.8(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    4558
_cell_measurement_theta_min      2.26
_cell_measurement_theta_max      25.40

_exptl_crystal_description       'rectangular plate'
_exptl_crystal_colour            brown
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.02
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.493
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             856
_exptl_absorpt_coefficient_mu    0.571
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.8658
_exptl_absorpt_correction_T_max  0.9887
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean 0.3
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            26070
_diffrn_reflns_av_R_equivalents  0.0979
_diffrn_reflns_av_unetl/netl     0.0717
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         2.26
_diffrn_reflns_theta_max         26.00
_reflns_number_total             3645
_reflns_number_gt                2288
_reflns_threshold_expression     >2σ(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    ORTEP-III
_computing_publication_material  WinGXv1.80.05

_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)+(0.1267P)²+4.0517P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3645
_refine_ls_number_parameters     246
_refine_ls_number_restraints     13
_refine_ls_R_factor_all          0.1296
_refine_ls_R_factor_gt           0.0831
_refine_ls_wR_factor_ref         0.2560
_refine_ls_wR_factor_gt          0.2028
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_restrained_S_all      1.063
_refine_ls_shift/su_max          0.005
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
V1 V 0.34248(6) 0.29248(17) 0.48670(5) 0.0435(4) Uani 1 1 d . . .
O1 O 0.2944(2) 0.0422(6) 0.4312(2) 0.0443(9) Uani 1 1 d . . .
O2 O 0.3371(2) 0.5156(7) 0.5621(2) 0.0483(10) Uani 1 1 d . . .
O5 O 0.1475(3) 0.9677(9) 0.5096(3) 0.0589(13) Uani 1 1 d . . .
O3 O 0.3763(3) 0.4250(8) 0.4303(3) 0.0621(12) Uani 1 1 d . . .
O4 O 0.4190(3) 0.1593(10) 0.5577(3) 0.0822(12) Uani 1 1 d . . .
N1 N 0.2279(3) 0.4164(7) 0.4436(2) 0.0383(10) Uani 1 1 d . . .
N2 N 0.2119(3) 0.5967(8) 0.4840(2) 0.0401(11) Uani 1 1 d . . .
C1 C 0.2371(3) 0.0155(9) 0.3615(3) 0.0395(12) Uani 1 1 d . . .
C2 C 0.2392(4) -0.1817(9) 0.3189(3) 0.0448(14) Uani 1 1 d . . .
H2 H 0.2792 -0.2860 0.3392 0.054 Uiso 1 1 calc R . .
C3 C 0.1828(4) -0.2184(9) 0.2484(3) 0.0461(14) Uani 1 1 d . . .
H3 H 0.1845 -0.3498 0.2212 0.055 Uiso 1 1 calc R . .
C4 C 0.1211(3) -0.0627(9) 0.2145(3) 0.0429(13) Uani 1 1 d . . .
C5 C 0.0653(4) -0.0967(11) 0.1397(3) 0.0508(15) Uani 1 1 d . . .
H5 H 0.0675 -0.2270 0.1122 0.061 Uiso 1 1 calc R . .
C6 C 0.0083(4) 0.0564(12) 0.1066(3) 0.0529(16) Uani 1 1 d . . .
H6 H -0.0279 0.0319 0.0568 0.063 Uiso 1 1 calc R . .
C7 C 0.0042(4) 0.2518(11) 0.1481(3) 0.0523(15) Uani 1 1 d . . .
H7 H -0.0344 0.3581 0.1253 0.063 Uiso 1 1 calc R . .
C8 C 0.0567(3) 0.2879(10) 0.2221(3) 0.0453(13) Uani 1 1 d . . .
H8 H 0.0521 0.4164 0.2493 0.054 Uiso 1 1 calc R . .
C9 C 0.1176(3) 0.1343(9) 0.2575(3) 0.0369(12) Uani 1 1 d . . .
C10 C 0.1762(3) 0.1691(9) 0.3336(3) 0.0364(12) Uani 1 1 d . . .
C11 C 0.1723(3) 0.3540(9) 0.3805(3) 0.0372(12) Uani 1 1 d . . .
H11 H 0.1263 0.4377 0.3650 0.045 Uiso 1 1 calc R . .
C12 C 0.2742(3) 0.6411(9) 0.5441(3) 0.0417(13) Uani 1 1 d . . .
C13 C 0.2744(3) 0.8327(9) 0.5953(3) 0.0396(13) Uani 1 1 d . . .
C14 C 0.2118(3) 0.9886(10) 0.5745(3) 0.0441(13) Uani 1 1 d . . .
C15 C 0.2153(4) 1.1723(10) 0.6217(3) 0.0517(15) Uani 1 1 d . . .
H15 H 0.1747 1.2764 0.6078 0.062 Uiso 1 1 calc R . .
C16 C 0.2785(4) 1.2030(11) 0.6892(4) 0.0590(17) Uani 1 1 d . . .
H16 H 0.2803 1.3284 0.7203 0.071 Uiso 1 1 calc R . .
C17 C 0.3389(4) 1.0508(12) 0.7113(4) 0.0594(17) Uani 1 1 d . . .
H17 H 0.3810 1.0723 0.7574 0.071 Uiso 1 1 calc R . .
C18 C 0.3369(4) 0.8653(11) 0.6646(3) 0.0516(15) Uani 1 1 d . . .
H18 H 0.3777 0.7618 0.6797 0.062 Uiso 1 1 calc R . .
C19 C 0.4980(4) 0.1932(13) 0.5950(5) 0.0822(12) Uani 1 1 d DU . .
H19A H 0.5056 0.3338 0.6238 0.099 Uiso 1 1 calc R . .
H19B H 0.5225 0.2083 0.5558 0.099 Uiso 1 1 calc R . .
C20 C 0.5376(4) 0.0106(14) 0.6497(4) 0.0822(12) Uani 1 1 d DU . .
H20A H 0.5128 -0.0090 0.6878 0.123 Uiso 1 1 calc R . .
H20B H 0.5915 0.0494 0.6757 0.123 Uiso 1 1 calc R . .
H20C H 0.5343 -0.1270 0.6211 0.123 Uiso 1 1 calc R . .
H5A H 0.150(4) 0.872(13) 0.485(4) 0.07(3) Uiso 1 1 d . . .


_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
V1 O3 1.579(4) . ?
V1 O4 1.731(5) . ?
V1 O1 1.840(4) . ?
V1 O2 1.936(4) . ?
V1 N1 2.096(5) . ?
O1 C1 1.345(6) . ?
O2 C12 1.312(7) . ?
O5 C14 1.352(7) . ?
O5 H5A 0.74(7) . ?
O4 C19 1.378(9) . ?
N1 C11 1.296(6) . ?
N1 N2 1.385(6) . ?
N2 C12 1.302(7) . ?
C1 C10 1.390(7) . ?
C1 C2 1.413(7) . ?
C2 C3 1.357(8) . ?
C2 H2 0.9300 . ?
C3 C4 1.421(8) . ?
C3 H3 0.9300 . ?
C4 C5 1.405(8) . ?
C4 C9 1.422(7) . ?
C5 C6 1.355(9) . ?
C5 H5 0.9300 . ?
C6 C7 1.401(9) . ?
C6 H6 0.9300 . ?
C7 C8 1.372(8) . ?
C7 H7 0.9300 . ?
C8 C9 1.409(8) . ?
C8 H8 0.9300 . ?
C9 C10 1.442(7) . ?
C10 C11 1.408(7) . ?
C11 H11 0.9300 . ?
C12 C13 1.471(7) . ?
C13 C18 1.391(8) . ?
C13 C14 1.415(8) . ?
C14 C15 1.377(8) . ?
C15 C16 1.374(9) . ?
C15 H15 0.9300 . ?
C16 C17 1.373(10) . ?
C16 H16 0.9300 . ?
C17 C18 1.385(9) . ?
C17 H17 0.9300 . ?
C18 H18 0.9300 . ?
C19 C20 1.480(7) . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?

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 V1 O4 108.6(3) . . ?
O3 V1 O1 105.3(2) . . ?
O4 V1 O1 98.6(2) . . ?
O3 V1 O2 104.4(2) . . ?
O4 V1 O2 90.5(2) . . ?
O1 V1 O2 144.20(18) . . ?
O3 V1 N1 98.4(2) . . ?
O4 V1 N1 151.8(2) . . ?
O1 V1 N1 81.65(17) . . ?
O2 V1 N1 74.66(16) . . ?
C1 O1 V1 132.8(3) . . ?
C12 O2 V1 117.8(3) . . ?
C14 O5 H5A 113(6) . . ?
C19 O4 V1 137.4(5) . . ?
C11 N1 N2 116.6(4) . . ?
C11 N1 V1 127.1(4) . . ?
N2 N1 V1 116.0(3) . . ?
C12 N2 N1 108.7(4) . . ?
O1 C1 C10 121.9(5) . . ?
O1 C1 C2 117.1(5) . . ?
C10 C1 C2 120.9(5) . . ?
C3 C2 C1 119.8(5) . . ?
C3 C2 H2 120.1 . . ?
C1 C2 H2 120.1 . . ?
C2 C3 C4 122.2(5) . . ?
C2 C3 H3 118.9 . . ?
C4 C3 H3 118.9 . . ?
C5 C4 C3 121.7(5) . . ?
C5 C4 C9 119.8(5) . . ?
C3 C4 C9 118.5(5) . . ?
C6 C5 C4 121.4(6) . . ?
C6 C5 H5 119.3 . . ?
C4 C5 H5 119.3 . . ?
C5 C6 C7 119.5(5) . . ?
C5 C6 H6 120.3 . . ?
C7 C6 H6 120.3 . . ?
C8 C7 C6 120.7(6) . . ?
C8 C7 H7 119.7 . . ?
C6 C7 H7 119.7 . . ?
C7 C8 C9 121.3(6) . . ?
C7 C8 H8 119.4 . . ?
C9 C8 H8 119.4 . . ?
C8 C9 C4 117.3(5) . . ?
C8 C9 C10 123.5(5) . . ?
C4 C9 C10 119.2(5) . . ?
C1 C10 C11 119.5(5) . . ?
C1 C10 C9 119.3(5) . . ?
C11 C10 C9 121.2(5) . . ?
N1 C11 C10 124.9(5) . . ?
N1 C11 H11 117.5 . . ?
C10 C11 H11 117.5 . . ?
N2 C12 O2 121.8(5) . . ?
N2 C12 C13 120.0(5) . . ?
O2 C12 C13 118.2(5) . . ?
C18 C13 C14 118.9(5) . . ?
C18 C13 C12 120.3(5) . . ?
C14 C13 C12 120.8(5) . . ?
O5 C14 C15 117.2(6) . . ?
O5 C14 C13 123.3(5) . . ?
C15 C14 C13 119.5(5) . . ?
C16 C15 C14 120.4(6) . . ?
C16 C15 H15 119.8 . . ?
C14 C15 H15 119.8 . . ?
C17 C16 C15 120.9(6) . . ?
C17 C16 H16 119.6 . . ?
C15 C16 H16 119.6 . . ?
C16 C17 C18 119.8(6) . . ?
C16 C17 H17 120.1 . . ?
C18 C17 H17 120.1 . . ?
C17 C18 C13 120.4(6) . . ?
C17 C18 H18 119.8 . . ?
C13 C18 H18 119.8 . . ?
O4 C19 C20 114.0(7) . . ?
O4 C19 H19A 108.7 . . ?
C20 C19 H19A 108.7 . . ?
O4 C19 H19B 108.7 . . ?
C20 C19 H19B 108.7 . . ?
H19A C19 H19B 107.6 . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C19 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O3 V1 O1 C1 -57.1(5) . . . . ?
O4 V1 O1 C1 -169.1(5) . . . . ?
O2 V1 O1 C1 88.0(5) . . . . ?
N1 V1 O1 C1 39.4(4) . . . . ?
O3 V1 O2 C12 86.3(4) . . . . ?
O4 V1 O2 C12 -164.4(4) . . . . ?
O1 V1 O2 C12 -59.0(5) . . . . ?
N1 V1 O2 C12 -8.6(4) . . . . ?
O3 V1 O4 C19 28.5(9) . . . . ?
O1 V1 O4 C19 137.9(8) . . . . ?
O2 V1 O4 C19 -76.9(8) . . . . ?
N1 V1 O4 C19 -133.8(8) . . . . ?
O3 V1 N1 C11 78.2(5) . . . . ?
O4 V1 N1 C11 -118.7(6) . . . . ?
O1 V1 N1 C11 -26.2(4) . . . . ?
O2 V1 N1 C11 -179.1(5) . . . . ?
O3 V1 N1 N2 -96.3(4) . . . . ?
O4 V1 N1 N2 66.8(6) . . . . ?
O1 V1 N1 N2 159.3(4) . . . . ?
O2 V1 N1 N2 6.4(3) . . . . ?
C11 N1 N2 C12 -178.2(4) . . . . ?
V1 N1 N2 C12 -3.1(5) . . . . ?
V1 O1 C1 C10 -33.3(7) . . . . ?
V1 O1 C1 C2 149.6(4) . . . . ?
O1 C1 C2 C3 179.7(5) . . . . ?
C10 C1 C2 C3 2.5(8) . . . . ?
C1 C2 C3 C4 0.8(8) . . . . ?
C2 C3 C4 C5 176.6(5) . . . . ?
C2 C3 C4 C9 -1.9(8) . . . . ?
C3 C4 C5 C6 -177.6(6) . . . . ?
C9 C4 C5 C6 0.9(9) . . . . ?
C4 C5 C6 C7 -0.7(9) . . . . ?
C5 C6 C7 C8 -0.8(9) . . . . ?
C6 C7 C8 C9 2.0(9) . . . . ?
C7 C8 C9 C4 -1.7(8) . . . . ?
C7 C8 C9 C10 177.3(5) . . . . ?
C5 C4 C9 C8 0.3(8) . . . . ?
C3 C4 C9 C8 178.8(5) . . . . ?
C5 C4 C9 C10 -178.8(5) . . . . ?
C3 C4 C9 C10 -0.2(7) . . . . ?
O1 C1 C10 C11 -2.3(8) . . . . ?
C2 C1 C10 C11 174.7(5) . . . . ?
O1 C1 C10 C9 178.3(5) . . . . ?
C2 C1 C10 C9 -4.6(8) . . . . ?
C8 C9 C10 C1 -175.6(5) . . . . ?
C4 C9 C10 C1 3.4(7) . . . . ?
C8 C9 C10 C11 5.1(8) . . . . ?
C4 C9 C10 C11 -175.9(5) . . . . ?
N2 N1 C11 C10 -177.1(5) . . . . ?
V1 N1 C11 C10 8.4(8) . . . . ?
C1 C10 C11 N1 11.7(8) . . . . ?
C9 C10 C11 N1 -169.0(5) . . . . ?
N1 N2 C12 O2 -4.4(7) . . . . ?
N1 N2 C12 C13 177.2(4) . . . . ?
V1 O2 C12 N2 10.7(7) . . . . ?
V1 O2 C12 C13 -171.0(3) . . . . ?
N2 C12 C13 C18 172.3(5) . . . . ?
O2 C12 C13 C18 -6.0(8) . . . . ?
N2 C12 C13 C14 -8.6(8) . . . . ?
O2 C12 C13 C14 173.0(5) . . . . ?
C18 C13 C14 O5 -178.0(5) . . . . ?
C12 C13 C14 O5 3.0(8) . . . . ?
C18 C13 C14 C15 2.1(8) . . . . ?
C12 C13 C14 C15 -176.9(5) . . . . ?
O5 C14 C15 C16 179.1(5) . . . . ?
C13 C14 C15 C16 -1.0(9) . . . . ?
C14 C15 C16 C17 -0.5(9) . . . . ?
C15 C16 C17 C18 0.8(10) . . . . ?
C16 C17 C18 C13 0.3(10) . . . . ?
C14 C13 C18 C17 -1.8(8) . . . . ?
C12 C13 C18 C17 177.2(5) . . . . ?
V1 O4 C19 C20 -176.2(6) . . . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        26.00
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         1.509
_refine_diff_density_min         -1.150
_refine_diff_density_rms         0.112
####################################################################### 
# 
# 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_SPD-65
_database_code_depnum_ccdc_archive 'CCDC 1482860'
_audit_update_record             
;
2016-05-31 deposited with the CCDC.
2016-10-17 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
bis[oxovadnadium (Z)-2-hydroxy-N-((E)-(2-oxidonaphthalen-1-yl)methylene)benzohydrazonate
ethanoate] 4,4'-bipyridine
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         '(C10 H8 N2){(C18 H12 N2 O3)(C2 H5 O)O V}2'
_chemical_formula_sum            'C50 H42 N6 O10 V2'
_chemical_formula_weight         988.77

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
V V 0.0687 2.1097 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      tetragonal
_space_group_IT_number           85
_space_group_name_H-M_alt        'P 4/n'
_space_group_name_Hall           '-P 4a'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-y+1/2, x, z'
'-x+1/2, -y+1/2, z'
'y, -x+1/2, z'
'-x, -y, -z'
'y-1/2, -x, -z'
'x-1/2, y-1/2, -z'
'-y, x-1/2, -z'

_cell_length_a                   21.5608(3)
_cell_length_b                   21.5608(3)
_cell_length_c                   10.1344(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     4711.16(19)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    6418
_cell_measurement_temperature    99.9(3)
_cell_measurement_theta_max      66.4769
_cell_measurement_theta_min      11.0923
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.394
_exptl_crystal_F_000             2040
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_description       square
_exptl_crystal_colour            'reddish black'
_exptl_crystal_size_max          0.1409
_exptl_crystal_size_mid          0.1037
_exptl_crystal_size_min          0.0504
_exptl_absorpt_coefficient_mu    3.872
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_T_max  1.178
_exptl_absorpt_correction_T_min  0.894
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.18t (release 05-06-2012 CrysAlis171 .NET)
(compiled Jun  5 2012,17:40:27)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
;
_exptl_special_details           
;
 ?
;
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega    9.00   37.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      -54.6574  -19.0000 -150.0000 28

#__ type_ start__ end____ width___ exp.time_
  2 omega -147.00  -71.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      -54.6574  -19.0000 -150.0000 76

#__ type_ start__ end____ width___ exp.time_
  3 omega  101.00  147.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       54.6574  111.0000  -35.0000 46

#__ type_ start__ end____ width___ exp.time_
  4 omega  104.00  169.00   1.0000   60.0000
omega____ theta____ kappa____ phi______ frames
    -      109.3147  111.0000    0.0000 65

#__ type_ start__ end____ width___ exp.time_
  5 omega  100.00  177.00   1.0000   60.0000
omega____ theta____ kappa____ phi______ frames
    -      109.3147  111.0000  -35.0000 77

#__ type_ start__ end____ width___ exp.time_
  6 omega   18.00   93.00   1.0000   60.0000
omega____ theta____ kappa____ phi______ frames
    -      109.3147  -25.0000  -90.0000 75

#__ type_ start__ end____ width___ exp.time_
  7 omega   53.00   88.00   1.0000   60.0000
omega____ theta____ kappa____ phi______ frames
    -      109.3147  -25.0000 -150.0000 35

#__ type_ start__ end____ width___ exp.time_
  8 omega -150.00  -79.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      -54.6574  -99.0000  -30.0000 71

#__ type_ start__ end____ width___ exp.time_
  9 omega   10.00  157.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       54.6574   77.0000   60.0000 147

#__ type_ start__ end____ width___ exp.time_
 10 omega   57.00  123.00   1.0000   60.0000
omega____ theta____ kappa____ phi______ frames
    -      109.3147  178.0000  150.0000 66
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0614722000
_diffrn_orient_matrix_UB_12      0.0093109000
_diffrn_orient_matrix_UB_13      0.0749318000
_diffrn_orient_matrix_UB_21      0.0153250000
_diffrn_orient_matrix_UB_22      -0.0692893000
_diffrn_orient_matrix_UB_23      -0.0178411000
_diffrn_orient_matrix_UB_31      0.0330641000
_diffrn_orient_matrix_UB_32      0.0148702000
_diffrn_orient_matrix_UB_33      -0.1309686000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.5418
_diffrn_source                   'SuperNova (Cu) X-ray Source'
_reflns_odcompleteness_completeness 98.63
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.49
_diffrn_ambient_temperature      99.9(2)
_diffrn_reflns_number            12631
_diffrn_reflns_av_unetI/netI     0.0278
_diffrn_reflns_av_R_equivalents  0.0317
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       6
_diffrn_reflns_theta_min         11.203
_diffrn_reflns_theta_max         66.586
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measured_fraction_theta_full 0.966
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_Laue_measured_fraction_full 0.966
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_point_group_measured_fraction_full 0.966
_reflns_number_total             4129
_reflns_number_gt                3576
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.18t (release 05-06-2012 CrysAlis171 .NET)
(compiled Jun  5 2012,17:40:27)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.18t (release 05-06-2012 CrysAlis171 .NET)
(compiled Jun  5 2012,17:40:27)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.18t (release 05-06-2012 CrysAlis171 .NET)
(compiled Jun  5 2012,17:40:27)
;
_computing_molecular_graphics    
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material  
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement  
;
SHELXL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0629P)²+1.3614P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4129
_refine_ls_number_parameters     381
_refine_ls_number_restraints     4
_refine_ls_R_factor_all          0.0452
_refine_ls_R_factor_gt           0.0377
_refine_ls_wR_factor_ref         0.1054
_refine_ls_wR_factor_gt          0.0994
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_restrained_S_all      1.042
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
V1 V 0.50775(2) 0.37868(2) 0.32114(3) 0.02591(13) Uani 1 1 d . . . . .
O3 O 0.44205(7) 0.41279(7) 0.33359(14) 0.0344(3) Uani 1 1 d . . . . .
O1 O 0.54488(6) 0.42546(6) 0.18963(13) 0.0279(3) Uani 1 1 d . . . . .
O2 O 0.50814(6) 0.33906(6) 0.49591(13) 0.0287(3) Uani 1 1 d . . . . .
O4 O 0.48703(6) 0.30754(7) 0.24398(14) 0.0318(3) Uani 1 1 d D . . . .
O5 O 0.61222(10) 0.41458(8) 0.80915(16) 0.0471(4) Uani 1 1 d . . . . .
N2 N 0.56761(8) 0.41931(8) 0.57240(16) 0.0292(4) Uani 1 1 d . . . . .
N1 N 0.55780(7) 0.43992(8) 0.44383(16) 0.0268(4) Uani 1 1 d . . . . .
N3 N 0.60584(8) 0.32833(8) 0.32069(16) 0.0262(4) Uani 1 1 d . . . . .
C22 C 0.66524(9) 0.23583(9) 0.3547(2) 0.0268(4) Uani 1 1 d . . . . .
C12 C 0.53969(9) 0.36580(9) 0.5892(2) 0.0277(4) Uani 1 1 d . . . . .
C21 C 0.61024(9) 0.26852(9) 0.3543(2) 0.0280(4) Uani 1 1 d . . . . .
C25 C 0.65858(9) 0.35730(9) 0.2863(2) 0.0265(4) Uani 1 1 d . . . . .
C1 C 0.56421(9) 0.48384(9) 0.1769(2) 0.0279(4) Uani 1 1 d . . . . .
C24 C 0.71564(9) 0.32846(9) 0.2842(2) 0.0262(4) Uani 1 1 d . . . . .
C10 C 0.58102(9) 0.52018(9) 0.2853(2) 0.0275(4) Uani 1 1 d . . . . .
C9 C 0.60287(9) 0.58302(9) 0.2641(2) 0.0293(4) Uani 1 1 d . . . . .
C11 C 0.58136(9) 0.49370(9) 0.4156(2) 0.0278(4) Uani 1 1 d . . . . .
C2 C 0.57044(9) 0.50687(10) 0.0466(2) 0.0320(5) Uani 1 1 d . . . . .
C23 C 0.71984(9) 0.26631(9) 0.31935(18) 0.0245(4) Uani 1 1 d . . . . .
C18 C 0.51549(9) 0.27761(10) 0.7388(2) 0.0333(5) Uani 1 1 d . . . . .
C4 C 0.60624(9) 0.60587(10) 0.1326(2) 0.0331(5) Uani 1 1 d . . . . .
C8 C 0.61995(10) 0.62337(10) 0.3677(2) 0.0336(5) Uani 1 1 d . . . . .
C3 C 0.59022(10) 0.56606(11) 0.0264(2) 0.0350(5) Uani 1 1 d . . . . .
C13 C 0.54520(10) 0.33472(10) 0.7185(2) 0.0312(4) Uani 1 1 d . . . . .
C17 C 0.52060(11) 0.24678(11) 0.8577(2) 0.0382(5) Uani 1 1 d . . . . .
C7 C 0.63858(11) 0.68330(11) 0.3426(3) 0.0392(5) Uani 1 1 d . . . . .
C5 C 0.62558(10) 0.66778(11) 0.1107(3) 0.0391(5) Uani 1 1 d . . . . .
C14 C 0.58091(12) 0.36024(10) 0.8209(2) 0.0364(5) Uani 1 1 d . . . . .
C6 C 0.64102(11) 0.70569(11) 0.2128(3) 0.0424(6) Uani 1 1 d . . . . .
C15 C 0.58593(13) 0.32838(12) 0.9407(2) 0.0444(6) Uani 1 1 d . . . . .
C19B C 0.4304(2) 0.2749(3) 0.2261(8) 0.0400(12) Uani 0.78(2) 1 d D . P A 1
H19C H 0.4274 0.2603 0.1358 0.048 Uiso 0.78(2) 1 calc R U P A 1
H19D H 0.3957 0.3024 0.2430 0.048 Uiso 0.78(2) 1 calc R U P A 1
C16 C 0.55596(12) 0.27244(12) 0.9587(2) 0.0427(6) Uani 1 1 d . . . . .
C20B C 0.42828(18) 0.22068(17) 0.3198(4) 0.0554(9) Uani 0.770(5) 1 d D . P A 1
H20E H 0.4608 0.1921 0.2982 0.083 Uiso 0.770(5) 1 calc R U P A 1
H20F H 0.3889 0.2002 0.3122 0.083 Uiso 0.770(5) 1 calc R U P A 1
H20D H 0.4338 0.2352 0.4085 0.083 Uiso 0.770(5) 1 calc R U P A 1
C20A C 0.4237(6) 0.2195(5) 0.1967(13) 0.0554(9) Uani 0.230(5) 1 d D . P A 2
H20A H 0.4244 0.2278 0.1037 0.083 Uiso 0.230(5) 1 calc R U P A 2
H20B H 0.3856 0.1989 0.2192 0.083 Uiso 0.230(5) 1 calc R U P A 2
H20C H 0.4581 0.1935 0.2196 0.083 Uiso 0.230(5) 1 calc R U P A 2
C19A C 0.4281(6) 0.2798(7) 0.272(2) 0.0400(12) Uani 0.22(2) 1 d D . P A 2
H19B H 0.3949 0.3075 0.2450 0.048 Uiso 0.22(2) 1 calc R U P A 2
H19A H 0.4241 0.2721 0.3657 0.048 Uiso 0.22(2) 1 calc R U P A 2
H8 H 0.6165(10) 0.6113(10) 0.457(2) 0.028(6) Uiso 1 1 d . . . . .
H18 H 0.4924(12) 0.2582(12) 0.662(3) 0.041(7) Uiso 1 1 d . . . . .
H5 H 0.6265(11) 0.6797(11) 0.021(3) 0.036(6) Uiso 1 1 d . . . . .
H3 H 0.5949(10) 0.5813(10) -0.060(2) 0.032(6) Uiso 1 1 d . . . . .
H11 H 0.6013(11) 0.5156(11) 0.486(2) 0.038(6) Uiso 1 1 d . . . . .
H25 H 0.6557(10) 0.3988(11) 0.263(2) 0.033(6) Uiso 1 1 d . . . . .
H2 H 0.5606(11) 0.4792(11) -0.025(3) 0.037(6) Uiso 1 1 d . . . . .
H21 H 0.5722(11) 0.2480(10) 0.373(2) 0.031(6) Uiso 1 1 d . . . . .
H16 H 0.5598(12) 0.2513(12) 1.041(3) 0.047(7) Uiso 1 1 d . . . . .
H24 H 0.7510(10) 0.3518(10) 0.252(2) 0.025(5) Uiso 1 1 d . . . . .
H22 H 0.6655(10) 0.1940(11) 0.382(2) 0.031(6) Uiso 1 1 d . . . . .
H7 H 0.6493(12) 0.7108(12) 0.419(3) 0.046(7) Uiso 1 1 d . . . . .
H17 H 0.5015(12) 0.2083(13) 0.870(3) 0.046(7) Uiso 1 1 d . . . . .
H15 H 0.6115(14) 0.3469(14) 1.010(3) 0.060(8) Uiso 1 1 d . . . . .
H6 H 0.6529(14) 0.7466(13) 0.192(3) 0.054(8) Uiso 1 1 d . . . . .
H5O H 0.6061(16) 0.4289(16) 0.728(4) 0.082(11) Uiso 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds 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
V1 O3 1.6010(15) . ?
V1 O4 1.7789(14) . ?
V1 O1 1.8532(14) . ?
V1 O2 1.9664(14) . ?
V1 N1 2.1103(17) . ?
V1 N3 2.3772(16) . ?
O1 C1 1.332(2) . ?
O2 C12 1.300(2) . ?
O4 C19B 1.420(3) . ?
O4 C19A 1.433(9) . ?
O5 C14 1.357(3) . ?
O5 H5O 0.89(4) . ?
N2 C12 1.312(3) . ?
N2 N1 1.393(2) . ?
N1 C11 1.298(3) . ?
N3 C21 1.337(3) . ?
N3 C25 1.343(3) . ?
C22 C21 1.380(3) . ?
C22 C23 1.395(3) . ?
C22 H22 0.94(2) . ?
C12 C13 1.476(3) . ?
C21 H21 0.95(2) . ?
C25 C24 1.379(3) . ?
C25 H25 0.93(2) . ?
C1 C10 1.397(3) . ?
C1 C2 1.417(3) . ?
C24 C23 1.390(3) . ?
C24 H24 0.97(2) . ?
C10 C11 1.439(3) . ?
C10 C9 1.450(3) . ?
C9 C8 1.412(3) . ?
C9 C4 1.423(3) . ?
C11 H11 0.96(3) . ?
C2 C3 1.361(3) . ?
C2 H2 0.96(3) . ?
C23 C23 1.478(4) 3_655 ?
C18 C17 1.381(3) . ?
C18 C13 1.403(3) . ?
C18 H18 1.01(3) . ?
C4 C5 1.416(3) . ?
C4 C3 1.419(3) . ?
C8 C7 1.377(3) . ?
C8 H8 0.95(2) . ?
C3 H3 0.94(2) . ?
C13 C14 1.405(3) . ?
C17 C16 1.391(4) . ?
C17 H17 0.93(3) . ?
C7 C6 1.402(4) . ?
C7 H7 1.00(3) . ?
C5 C6 1.359(4) . ?
C5 H5 0.95(3) . ?
C14 C15 1.399(3) . ?
C6 H6 0.94(3) . ?
C15 C16 1.380(4) . ?
C15 H15 0.98(3) . ?
C19B C20B 1.507(5) . ?
C19B H19C 0.9700 . ?
C19B H19D 0.9700 . ?
C16 H16 0.95(3) . ?
C20B H20E 0.9600 . ?
C20B H20F 0.9600 . ?
C20B H20D 0.9600 . ?
C20A C19A 1.509(9) . ?
C20A H20A 0.9600 . ?
C20A H20B 0.9600 . ?
C20A H20C 0.9600 . ?
C19A H19B 0.9700 . ?
C19A H19A 0.9700 . ?

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 V1 O4 102.03(7) . . ?
O3 V1 O1 100.89(7) . . ?
O4 V1 O1 105.17(6) . . ?
O3 V1 O2 97.60(7) . . ?
O4 V1 O2 91.29(6) . . ?
O1 V1 O2 151.93(6) . . ?
O3 V1 N1 96.82(7) . . ?
O4 V1 N1 157.97(7) . . ?
O1 V1 N1 82.09(6) . . ?
O2 V1 N1 74.87(6) . . ?
O3 V1 N3 175.58(7) . . ?
O4 V1 N3 80.14(6) . . ?
O1 V1 N3 82.12(6) . . ?
O2 V1 N3 78.44(6) . . ?
N1 V1 N3 80.33(6) . . ?
C1 O1 V1 135.98(13) . . ?
C12 O2 V1 117.71(13) . . ?
C19B O4 V1 134.3(4) . . ?
C19A O4 V1 119.7(5) . . ?
C14 O5 H5O 108(2) . . ?
C12 N2 N1 109.42(16) . . ?
C11 N1 N2 115.58(17) . . ?
C11 N1 V1 128.99(14) . . ?
N2 N1 V1 115.42(12) . . ?
C21 N3 C25 117.02(17) . . ?
C21 N3 V1 120.20(13) . . ?
C25 N3 V1 122.77(13) . . ?
C21 C22 C23 118.95(18) . . ?
C21 C22 H22 119.6(14) . . ?
C23 C22 H22 121.3(14) . . ?
O2 C12 N2 122.36(18) . . ?
O2 C12 C13 119.10(19) . . ?
N2 C12 C13 118.53(18) . . ?
N3 C21 C22 123.67(19) . . ?
N3 C21 H21 116.1(14) . . ?
C22 C21 H21 120.1(14) . . ?
N3 C25 C24 123.35(18) . . ?
N3 C25 H25 117.3(14) . . ?
C24 C25 H25 119.3(14) . . ?
O1 C1 C10 122.33(18) . . ?
O1 C1 C2 116.82(18) . . ?
C10 C1 C2 120.76(19) . . ?
C25 C24 C23 119.28(18) . . ?
C25 C24 H24 118.2(12) . . ?
C23 C24 H24 122.4(12) . . ?
C1 C10 C11 120.03(19) . . ?
C1 C10 C9 119.45(19) . . ?
C11 C10 C9 120.33(19) . . ?
C8 C9 C4 118.0(2) . . ?
C8 C9 C10 123.4(2) . . ?
C4 C9 C10 118.60(19) . . ?
N1 C11 C10 123.70(19) . . ?
N1 C11 H11 117.0(15) . . ?
C10 C11 H11 119.2(15) . . ?
C3 C2 C1 119.9(2) . . ?
C3 C2 H2 122.4(15) . . ?
C1 C2 H2 117.7(15) . . ?
C24 C23 C22 117.72(17) . . ?
C24 C23 C23 121.1(2) . 3_655 ?
C22 C23 C23 121.2(2) . 3_655 ?
C17 C18 C13 120.9(2) . . ?
C17 C18 H18 120.7(15) . . ?
C13 C18 H18 118.2(15) . . ?
C5 C4 C3 121.6(2) . . ?
C5 C4 C9 119.2(2) . . ?
C3 C4 C9 119.24(19) . . ?
C7 C8 C9 121.1(2) . . ?
C7 C8 H8 117.1(14) . . ?
C9 C8 H8 121.6(14) . . ?
C2 C3 C4 122.0(2) . . ?
C2 C3 H3 120.1(14) . . ?
C4 C3 H3 117.9(14) . . ?
C18 C13 C14 119.0(2) . . ?
C18 C13 C12 119.5(2) . . ?
C14 C13 C12 121.5(2) . . ?
C18 C17 C16 119.6(2) . . ?
C18 C17 H17 120.5(17) . . ?
C16 C17 H17 119.8(17) . . ?
C8 C7 C6 120.5(2) . . ?
C8 C7 H7 118.7(15) . . ?
C6 C7 H7 120.8(15) . . ?
C6 C5 C4 121.3(2) . . ?
C6 C5 H5 124.3(15) . . ?
C4 C5 H5 114.4(15) . . ?
O5 C14 C15 117.5(2) . . ?
O5 C14 C13 123.10(19) . . ?
C15 C14 C13 119.4(2) . . ?
C5 C6 C7 119.8(2) . . ?
C5 C6 H6 117.1(17) . . ?
C7 C6 H6 123.1(17) . . ?
C16 C15 C14 120.5(2) . . ?
C16 C15 H15 121.9(18) . . ?
C14 C15 H15 117.6(18) . . ?
O4 C19B C20B 109.2(3) . . ?
O4 C19B H19C 109.8 . . ?
C20B C19B H19C 109.8 . . ?
O4 C19B H19D 109.8 . . ?
C20B C19B H19D 109.8 . . ?
H19C C19B H19D 108.3 . . ?
C15 C16 C17 120.5(2) . . ?
C15 C16 H16 119.5(16) . . ?
C17 C16 H16 120.0(16) . . ?
C19B C20B H20E 109.5 . . ?
C19B C20B H20F 109.5 . . ?
H20E C20B H20F 109.5 . . ?
C19B C20B H20D 109.5 . . ?
H20E C20B H20D 109.5 . . ?
H20F C20B H20D 109.5 . . ?
C19A C20A H20A 109.5 . . ?
C19A C20A H20B 109.5 . . ?
H20A C20A H20B 109.5 . . ?
C19A C20A H20C 109.5 . . ?
H20A C20A H20C 109.5 . . ?
H20B C20A H20C 109.5 . . ?
O4 C19A C20A 108.4(9) . . ?
O4 C19A H19B 110.0 . . ?
C20A C19A H19B 110.0 . . ?
O4 C19A H19A 110.0 . . ?
C20A C19A H19A 110.0 . . ?
H19B C19A H19A 108.4 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O3 V1 O1 C1 65.29(18) . . . . ?
O4 V1 O1 C1 171.08(17) . . . . ?
O2 V1 O1 C1 -65.0(2) . . . . ?
N1 V1 O1 C1 -30.17(18) . . . . ?
N3 V1 O1 C1 -111.43(18) . . . . ?
O3 V1 O4 C19B -17.1(3) . . . . ?
O1 V1 O4 C19B -122.0(3) . . . . ?
O2 V1 O4 C19B 81.0(3) . . . . ?
N1 V1 O4 C19B 131.2(4) . . . . ?
N3 V1 O4 C19B 159.0(3) . . . . ?
O3 V1 O4 C19A -33.0(13) . . . . ?
O1 V1 O4 C19A -137.9(13) . . . . ?
O2 V1 O4 C19A 65.1(13) . . . . ?
N1 V1 O4 C19A 115.2(13) . . . . ?
N3 V1 O4 C19A 143.1(13) . . . . ?
C12 N2 N1 C11 177.73(16) . . . . ?
C12 N2 N1 V1 -3.12(19) . . . . ?
V1 O2 C12 N2 4.1(2) . . . . ?
V1 O2 C12 C13 -175.05(13) . . . . ?
N1 N2 C12 O2 -0.4(2) . . . . ?
N1 N2 C12 C13 178.74(16) . . . . ?
C25 N3 C21 C22 -0.3(3) . . . . ?
V1 N3 C21 C22 179.06(15) . . . . ?
C23 C22 C21 N3 0.5(3) . . . . ?
C21 N3 C25 C24 0.1(3) . . . . ?
V1 N3 C25 C24 -179.24(15) . . . . ?
V1 O1 C1 C10 24.8(3) . . . . ?
V1 O1 C1 C2 -158.59(14) . . . . ?
N3 C25 C24 C23 -0.1(3) . . . . ?
O1 C1 C10 C11 3.8(3) . . . . ?
C2 C1 C10 C11 -172.67(18) . . . . ?
O1 C1 C10 C9 178.75(16) . . . . ?
C2 C1 C10 C9 2.3(3) . . . . ?
C1 C10 C9 C8 179.02(18) . . . . ?
C11 C10 C9 C8 -6.0(3) . . . . ?
C1 C10 C9 C4 0.3(3) . . . . ?
C11 C10 C9 C4 175.27(17) . . . . ?
N2 N1 C11 C10 174.14(17) . . . . ?
V1 N1 C11 C10 -4.9(3) . . . . ?
C1 C10 C11 N1 -11.0(3) . . . . ?
C9 C10 C11 N1 174.01(17) . . . . ?
O1 C1 C2 C3 -179.74(18) . . . . ?
C10 C1 C2 C3 -3.1(3) . . . . ?
C25 C24 C23 C22 0.4(3) . . . . ?
C25 C24 C23 C23 -179.57(14) . . . 3_655 ?
C21 C22 C23 C24 -0.6(3) . . . . ?
C21 C22 C23 C23 179.39(14) . . . 3_655 ?
C8 C9 C4 C5 -0.8(3) . . . . ?
C10 C9 C4 C5 177.98(17) . . . . ?
C8 C9 C4 C3 179.08(18) . . . . ?
C10 C9 C4 C3 -2.1(3) . . . . ?
C4 C9 C8 C7 0.8(3) . . . . ?
C10 C9 C8 C7 -177.94(19) . . . . ?
C1 C2 C3 C4 1.2(3) . . . . ?
C5 C4 C3 C2 -178.7(2) . . . . ?
C9 C4 C3 C2 1.4(3) . . . . ?
C17 C18 C13 C14 0.5(3) . . . . ?
C17 C18 C13 C12 178.86(18) . . . . ?
O2 C12 C13 C18 -1.1(3) . . . . ?
N2 C12 C13 C18 179.72(18) . . . . ?
O2 C12 C13 C14 177.24(18) . . . . ?
N2 C12 C13 C14 -2.0(3) . . . . ?
C13 C18 C17 C16 -0.4(3) . . . . ?
C9 C8 C7 C6 0.0(3) . . . . ?
C3 C4 C5 C6 -179.8(2) . . . . ?
C9 C4 C5 C6 0.1(3) . . . . ?
C18 C13 C14 O5 178.7(2) . . . . ?
C12 C13 C14 O5 0.3(3) . . . . ?
C18 C13 C14 C15 -0.2(3) . . . . ?
C12 C13 C14 C15 -178.5(2) . . . . ?
C4 C5 C6 C7 0.7(3) . . . . ?
C8 C7 C6 C5 -0.8(3) . . . . ?
O5 C14 C15 C16 -179.1(2) . . . . ?
C13 C14 C15 C16 -0.2(4) . . . . ?
C19A O4 C19B C20B -58(3) . . . . ?
V1 O4 C19B C20B -104.6(4) . . . . ?
C14 C15 C16 C17 0.3(4) . . . . ?
C18 C17 C16 C15 0.0(3) . . . . ?
C19B O4 C19A C20A 38.1(19) . . . . ?
V1 O4 C19A C20A -178.4(10) . . . . ?

_refine_diff_density_max         0.749
_refine_diff_density_min         -0.289
_refine_diff_density_rms         0.052

_shelxl_version_number           2013-4

