# Electronic Supplementary Material (ESI) for Dalton Transactions
# This journal is © The Royal Society of Chemistry 2013


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#  experimental, refinement, atomic coordinates, 
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted. 
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data_manar115
_database_code_depnum_ccdc_archive 'CCDC 924327'
#TrackingRef 'MANAR115.CIF'
_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C21 H17 N6 O5 V,2(O),2(H2 O),H O'
_chemical_formula_sum            'C21 H27 N6 O10 V'
_chemical_formula_weight         574.43
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           Orthorhombic
_symmetry_space_group_name_H-M   Pbca
_symmetry_space_group_name_Hall  -P2ac2ab
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'-x-1/2, y-1/2, z'
'x, -y-1/2, z-1/2'
_cell_length_a                   16.115(5)
_cell_length_b                   12.857(5)
_cell_length_c                   23.586(5)
_cell_angle_alpha                90.000(5)
_cell_angle_beta                 90.000(5)
_cell_angle_gamma                90.000(5)
_cell_volume                     4887(3)
_cell_formula_units_Z            8
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    4217
_cell_measurement_theta_min      4406
_cell_measurement_theta_max      49543
_exptl_crystal_description       Plate
_exptl_crystal_colour            brown
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.37
_exptl_crystal_size_min          0.04
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.562
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             2384
_exptl_absorpt_coefficient_mu    0.475
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8401
_exptl_absorpt_correction_T_max  0.9813
_exptl_absorpt_process_details   'North et al., 1968'
_exptl_special_details           
;
?
;
_diffrn_ambient_temperature      100(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  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            27082
_diffrn_reflns_av_R_equivalents  0.0745
_diffrn_reflns_av_unetI/netI     0.0604
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_theta_min         2.14
_diffrn_reflns_theta_max         25.04
_reflns_number_total             4298
_reflns_number_gt                2879
_reflns_threshold_expression     >2sigma(I)
_computing_data_collection       'Apex2, Bruker Instrument Service v2010, 1-2'
_computing_cell_refinement       
'SAINT V7.68A (Bruker: Madison, 2009 ) in Apex2 suite.'
_computing_data_reduction        
'SAINT and XPREP Version 2008/2 (Sheldrick, Bruker AXS Inc.)'
_computing_structure_solution    
'XS Version 2008/1 (George M. Sheldrick, Acta Cryst. (2008). A64, 112-122) '
_computing_structure_refinement  
'XL Version 2008/4 (George M. Sheldrick, Acta Cryst. (2008). A64, 112-122)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          
;
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger. 4 restraints correspond to DFIX
instruction to fix the distances of located hydrogen atoms of water molecules
in difference map.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[\s^2^(Fo^2^)+(0.0909P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/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         4298
_refine_ls_number_parameters     400
_refine_ls_number_restraints     4
_refine_ls_R_factor_all          0.0832
_refine_ls_R_factor_gt           0.0517
_refine_ls_wR_factor_ref         0.1578
_refine_ls_wR_factor_gt          0.1380
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_restrained_S_all      1.043
_refine_ls_shift/su_max          0.000
_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 0.01588(4) 0.18857(5) 0.19605(3) 0.0240(2) Uani 1 1 d . . .
O1W O 0.0027(2) 0.1514(3) -0.06234(17) 0.0643(11) Uani 1 1 d . . .
N1 N 0.2503(2) -0.1334(3) 0.36407(16) 0.0269(8) Uani 1 1 d . . .
H1N H 0.269(2) -0.169(3) 0.3828(16) 0.013(12) Uiso 1 1 d . . .
C1 C 0.2848(2) -0.0383(3) 0.36439(18) 0.0291(10) Uani 1 1 d . . .
H1 H 0.327(2) -0.033(3) 0.3862(16) 0.025(11) Uiso 1 1 d . . .
O1 O 0.06940(14) 0.07976(19) 0.24345(11) 0.0226(6) Uani 1 1 d . . .
N2 N 0.17961(18) 0.1903(2) 0.26069(13) 0.0227(7) Uani 1 1 d . . .
C2 C 0.2498(2) 0.0401(3) 0.33395(18) 0.0284(10) Uani 1 1 d . . .
H2 H 0.273(2) 0.098(3) 0.3385(17) 0.031(12) Uiso 1 1 d . . .
O2W O 0.0320(2) 0.1115(3) -0.17131(16) 0.0584(10) Uani 1 1 d . . .
O2 O -0.21418(18) 0.6220(2) -0.00398(12) 0.0348(7) Uani 1 1 d . . .
O3 O -0.05379(16) 0.1113(2) 0.16676(14) 0.0454(8) Uani 1 1 d . . .
N3 N 0.13305(17) 0.2532(2) 0.22433(13) 0.0206(7) Uani 1 1 d . . .
C3 C 0.1781(2) 0.0217(3) 0.30317(16) 0.0212(8) Uani 1 1 d . . .
O3W O -0.3637(2) 0.7391(2) -0.00120(14) 0.0519(9) Uani 1 1 d D . .
H3WA H -0.3306 0.7401 0.0351 0.062 Uiso 1 1 d RD . .
H3WB H -0.3840 0.6683 0.0095 0.062 Uiso 1 1 d RD . .
C4 C 0.1815(2) -0.1537(3) 0.33535(18) 0.0278(10) Uani 1 1 d . . .
H4 H 0.164(2) -0.219(3) 0.3389(16) 0.027(11) Uiso 1 1 d . . .
O4 O -0.03262(15) 0.2520(2) 0.24549(12) 0.0332(7) Uani 1 1 d . . .
N4 N -0.09742(18) 0.5071(2) 0.04878(13) 0.0235(7) Uani 1 1 d . . .
O4W O 0.3507(2) -0.2629(2) 0.41713(14) 0.0392(8) Uani 1 1 d . . .
H4WA H 0.394(2) -0.237(3) 0.4263(16) 0.017(11) Uiso 1 1 d . . .
O5 O 0.02224(14) 0.29827(19) 0.14134(11) 0.0230(6) Uani 1 1 d . . .
N5 N -0.1559(2) 0.4642(3) 0.01285(14) 0.0232(7) Uani 1 1 d . . .
H5N H -0.159(3) 0.402(4) 0.0119(18) 0.037(14) Uiso 1 1 d . . .
C5 C 0.1440(2) -0.0772(3) 0.30449(17) 0.0246(9) Uani 1 1 d . . .
H5 H 0.098(2) -0.092(3) 0.2854(16) 0.023(10) Uiso 1 1 d . . .
O5W O -0.4395(2) 0.5570(3) 0.05588(17) 0.0767(12) Uani 1 1 d D . .
H5WB H -0.4717 0.6142 0.0371 0.092 Uiso 1 1 d RD . .
H5WA H -0.4571 0.4818 0.0488 0.092 Uiso 1 1 d RD . .
N6 N -0.38465(18) 0.3887(2) -0.12696(13) 0.0232(7) Uani 1 1 d . . .
C6 C 0.1392(2) 0.1027(3) 0.26734(15) 0.0203(8) Uani 1 1 d . . .
C7 C 0.1588(2) 0.3476(3) 0.21836(17) 0.0234(9) Uani 1 1 d . . .
H7 H 0.211(3) 0.363(3) 0.2419(16) 0.031(11) Uiso 1 1 d . . .
C8 C 0.1169(2) 0.4224(3) 0.18254(16) 0.0215(8) Uani 1 1 d . . .
C9 C 0.1447(2) 0.5253(3) 0.18371(17) 0.0228(9) Uani 1 1 d . . .
H9 H 0.183(2) 0.543(3) 0.2109(16) 0.024(10) Uiso 1 1 d . . .
C10 C 0.1118(2) 0.6022(3) 0.14954(16) 0.0215(8) Uani 1 1 d . . .
C11 C 0.0479(2) 0.5735(3) 0.11267(16) 0.0226(9) Uani 1 1 d . . .
H11 H 0.021(2) 0.622(3) 0.0939(15) 0.017(10) Uiso 1 1 d . . .
C12 C 0.0178(2) 0.4719(3) 0.11020(16) 0.0203(8) Uani 1 1 d . . .
C13 C -0.0487(2) 0.4411(3) 0.07133(16) 0.0232(8) Uani 1 1 d . . .
H13 H -0.056(2) 0.363(3) 0.0620(15) 0.022(10) Uiso 1 1 d . . .
C14 C -0.2120(2) 0.5266(3) -0.01168(16) 0.0262(9) Uani 1 1 d . . .
C15 C -0.2725(2) 0.4756(3) -0.05014(16) 0.0223(8) Uani 1 1 d . . .
C16 C -0.3041(2) 0.3767(3) -0.04175(18) 0.0279(9) Uani 1 1 d . . .
H16 H -0.292(2) 0.341(3) -0.0082(15) 0.017(10) Uiso 1 1 d . . .
C17 C -0.3593(2) 0.3366(3) -0.08121(18) 0.0279(9) Uani 1 1 d . . .
H17 H -0.384(2) 0.268(3) -0.0728(16) 0.031(11) Uiso 1 1 d . . .
C18 C -0.3559(2) 0.4853(3) -0.13350(17) 0.0245(9) Uani 1 1 d . . .
H18 H -0.380(2) 0.523(3) -0.1641(17) 0.032(11) Uiso 1 1 d . . .
C19 C -0.3001(2) 0.5313(3) -0.09693(16) 0.0243(9) Uani 1 1 d . . .
H19 H -0.2812 0.5985 -0.1035 0.029 Uiso 1 1 calc R . .
C20 C 0.1467(2) 0.7112(3) 0.15026(17) 0.0272(9) Uani 1 1 d . . .
H20A H 0.1695 0.7258 0.1870 0.041 Uiso 1 1 calc R . .
H20B H 0.1032 0.7601 0.1421 0.041 Uiso 1 1 calc R . .
H20C H 0.1894 0.7172 0.1221 0.041 Uiso 1 1 calc R . .
C21 C 0.0517(2) 0.3946(3) 0.14524(16) 0.0210(8) Uani 1 1 d . . .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
V1 0.0155(3) 0.0163(4) 0.0404(4) 0.0055(3) -0.0002(3) -0.0005(3)
O1W 0.057(2) 0.059(3) 0.078(3) 0.000(2) 0.0045(19) -0.0069(19)
N1 0.0243(18) 0.0188(19) 0.038(2) 0.0113(18) 0.0015(16) 0.0045(16)
C1 0.024(2) 0.024(2) 0.039(2) 0.005(2) -0.0059(19) -0.0042(18)
O1 0.0181(12) 0.0154(14) 0.0343(15) 0.0040(12) 0.0025(11) -0.0014(11)
N2 0.0207(15) 0.0148(17) 0.0325(18) 0.0047(15) 0.0010(14) 0.0015(13)
C2 0.028(2) 0.016(2) 0.041(2) 0.003(2) -0.0054(19) -0.0035(19)
O2W 0.046(2) 0.056(2) 0.073(2) 0.016(2) 0.0021(18) 0.0005(17)
O2 0.0482(17) 0.0153(15) 0.0410(18) -0.0038(14) -0.0168(14) 0.0037(12)
O3 0.0201(14) 0.044(2) 0.072(2) -0.0164(18) 0.0009(15) -0.0095(14)
N3 0.0177(15) 0.0160(17) 0.0281(17) 0.0043(14) 0.0005(13) 0.0045(13)
C3 0.0193(18) 0.016(2) 0.028(2) -0.0002(17) 0.0055(16) 0.0008(15)
O3W 0.072(2) 0.0253(17) 0.058(2) 0.0023(16) 0.0232(18) 0.0045(16)
C4 0.019(2) 0.018(2) 0.046(3) 0.004(2) 0.0072(19) -0.0001(17)
O4 0.0249(14) 0.0271(16) 0.0478(18) 0.0069(15) 0.0070(12) 0.0065(13)
N4 0.0273(17) 0.0169(17) 0.0264(17) -0.0029(14) -0.0032(14) -0.0004(14)
O4W 0.0395(19) 0.0302(18) 0.048(2) 0.0111(15) -0.0038(16) 0.0041(16)
O5 0.0219(13) 0.0131(14) 0.0338(15) 0.0011(12) -0.0022(11) 0.0007(11)
N5 0.0313(18) 0.0125(18) 0.0259(18) -0.0008(15) -0.0062(14) -0.0011(15)
C5 0.0162(19) 0.021(2) 0.037(2) 0.0014(19) 0.0054(17) -0.0013(17)
O5W 0.064(2) 0.080(3) 0.086(3) -0.001(3) 0.008(2) 0.006(2)
N6 0.0224(16) 0.0150(17) 0.0321(18) 0.0015(15) -0.0016(14) 0.0000(14)
C6 0.0161(18) 0.0155(19) 0.029(2) 0.0012(17) 0.0033(15) 0.0008(15)
C7 0.0209(19) 0.017(2) 0.033(2) 0.0037(18) 0.0003(17) 0.0015(17)
C8 0.0190(18) 0.015(2) 0.031(2) 0.0036(17) 0.0022(15) 0.0045(16)
C9 0.0185(19) 0.018(2) 0.032(2) -0.0003(18) -0.0019(17) -0.0012(16)
C10 0.0192(18) 0.0136(19) 0.032(2) 0.0001(17) 0.0049(16) 0.0000(16)
C11 0.024(2) 0.016(2) 0.028(2) 0.0030(18) 0.0000(17) 0.0085(17)
C12 0.0203(17) 0.014(2) 0.026(2) -0.0005(17) 0.0006(16) 0.0011(15)
C13 0.0265(19) 0.015(2) 0.028(2) 0.0013(18) 0.0034(16) 0.0006(17)
C14 0.036(2) 0.019(2) 0.024(2) -0.0018(18) -0.0036(17) 0.0006(18)
C15 0.0245(19) 0.016(2) 0.027(2) -0.0017(17) 0.0004(16) 0.0023(16)
C16 0.036(2) 0.022(2) 0.026(2) 0.0047(19) -0.0053(18) 0.0014(18)
C17 0.032(2) 0.017(2) 0.035(2) 0.0022(19) -0.0002(18) -0.0035(18)
C18 0.025(2) 0.017(2) 0.031(2) 0.0023(19) -0.0039(18) 0.0002(17)
C19 0.028(2) 0.013(2) 0.033(2) 0.0008(18) 0.0015(17) 0.0012(16)
C20 0.028(2) 0.018(2) 0.036(2) 0.0023(19) 0.0018(17) -0.0015(17)
C21 0.0171(17) 0.0114(19) 0.035(2) -0.0037(17) 0.0062(16) 0.0004(15)
_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 O4 1.623(3) . ?
V1 O3 1.650(3) . ?
V1 O5 1.914(3) . ?
V1 O1 1.988(3) . ?
V1 N3 2.168(3) . ?
V1 N6 2.493(3) 3 ?
N1 C4 1.325(5) . ?
N1 C1 1.343(5) . ?
N1 H1N 0.70(4) . ?
C1 C2 1.360(6) . ?
C1 H1 0.86(4) . ?
O1 C6 1.293(4) . ?
N2 C6 1.310(5) . ?
N2 N3 1.397(4) . ?
C2 C3 1.384(5) . ?
C2 H2 0.84(4) . ?
O2 C14 1.241(4) . ?
N3 C7 1.290(5) . ?
C3 C5 1.386(5) . ?
C3 C6 1.480(5) . ?
O3W H3WA 1.0093 . ?
O3W H3WB 1.0000 . ?
C4 C5 1.365(6) . ?
C4 H4 0.89(4) . ?
N4 C13 1.273(5) . ?
N4 N5 1.383(4) . ?
O4W H4WA 0.80(4) . ?
O5 C21 1.330(4) . ?
N5 C14 1.340(5) . ?
N5 H5N 0.80(5) . ?
C5 H5 0.89(4) . ?
O5W H5WB 1.0047 . ?
O5W H5WA 1.0209 . ?
N6 C18 1.334(5) . ?
N6 C17 1.334(5) . ?
N6 V1 2.493(3) 3_455 ?
C7 C8 1.448(5) . ?
C7 H7 1.03(4) . ?
C8 C9 1.398(5) . ?
C8 C21 1.415(5) . ?
C9 C10 1.381(5) . ?
C9 H9 0.92(4) . ?
C10 C11 1.397(5) . ?
C10 C20 1.511(5) . ?
C11 C12 1.395(5) . ?
C11 H11 0.87(4) . ?
C12 C21 1.404(5) . ?
C12 C13 1.464(5) . ?
C13 H13 1.04(4) . ?
C14 C15 1.484(5) . ?
C15 C19 1.388(5) . ?
C15 C16 1.384(5) . ?
C16 C17 1.387(6) . ?
C16 H16 0.94(4) . ?
C17 H17 0.99(4) . ?
C18 C19 1.379(5) . ?
C18 H18 0.95(4) . ?
C19 H19 0.9300 . ?
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
O4 V1 O3 105.99(15) . . ?
O4 V1 O5 98.04(13) . . ?
O3 V1 O5 101.40(15) . . ?
O4 V1 O1 99.11(13) . . ?
O3 V1 O1 96.15(14) . . ?
O5 V1 O1 150.98(10) . . ?
O4 V1 N3 90.33(13) . . ?
O3 V1 N3 162.14(13) . . ?
O5 V1 N3 83.02(11) . . ?
O1 V1 N3 73.66(11) . . ?
O4 V1 N6 168.38(12) . 3 ?
O3 V1 N6 85.63(13) . 3 ?
O5 V1 N6 79.55(11) . 3 ?
O1 V1 N6 78.93(10) . 3 ?
N3 V1 N6 78.10(11) . 3 ?
C4 N1 C1 121.8(4) . . ?
C4 N1 H1N 124(3) . . ?
C1 N1 H1N 114(3) . . ?
N1 C1 C2 120.0(4) . . ?
N1 C1 H1 114(3) . . ?
C2 C1 H1 126(3) . . ?
C6 O1 V1 117.6(2) . . ?
C6 N2 N3 107.7(3) . . ?
C1 C2 C3 119.8(4) . . ?
C1 C2 H2 114(3) . . ?
C3 C2 H2 126(3) . . ?
C7 N3 N2 116.0(3) . . ?
C7 N3 V1 127.4(3) . . ?
N2 N3 V1 115.8(2) . . ?
C2 C3 C5 118.4(4) . . ?
C2 C3 C6 122.2(3) . . ?
C5 C3 C6 119.3(3) . . ?
H3WA O3W H3WB 88.3 . . ?
N1 C4 C5 120.2(4) . . ?
N1 C4 H4 114(3) . . ?
C5 C4 H4 126(3) . . ?
C13 N4 N5 114.3(3) . . ?
C21 O5 V1 131.2(2) . . ?
C14 N5 N4 119.1(3) . . ?
C14 N5 H5N 123(3) . . ?
N4 N5 H5N 118(3) . . ?
C4 C5 C3 119.8(4) . . ?
C4 C5 H5 119(3) . . ?
C3 C5 H5 121(3) . . ?
H5WB O5W H5WA 118.4 . . ?
C18 N6 C17 117.1(3) . . ?
C18 N6 V1 121.3(3) . 3_455 ?
C17 N6 V1 121.7(2) . 3_455 ?
O1 C6 N2 125.2(3) . . ?
O1 C6 C3 117.2(3) . . ?
N2 C6 C3 117.5(3) . . ?
N3 C7 C8 122.6(3) . . ?
N3 C7 H7 113(2) . . ?
C8 C7 H7 124(2) . . ?
C9 C8 C21 119.3(3) . . ?
C9 C8 C7 117.9(3) . . ?
C21 C8 C7 122.8(3) . . ?
C10 C9 C8 122.9(4) . . ?
C10 C9 H9 119(2) . . ?
C8 C9 H9 118(2) . . ?
C9 C10 C11 117.3(3) . . ?
C9 C10 C20 121.0(3) . . ?
C11 C10 C20 121.7(3) . . ?
C10 C11 C12 121.9(4) . . ?
C10 C11 H11 119(2) . . ?
C12 C11 H11 118(2) . . ?
C11 C12 C21 120.2(3) . . ?
C11 C12 C13 122.3(3) . . ?
C21 C12 C13 117.5(3) . . ?
N4 C13 C12 122.2(3) . . ?
N4 C13 H13 119(2) . . ?
C12 C13 H13 119(2) . . ?
O2 C14 N5 123.2(4) . . ?
O2 C14 C15 120.5(4) . . ?
N5 C14 C15 116.3(3) . . ?
C19 C15 C16 118.0(3) . . ?
C19 C15 C14 117.9(3) . . ?
C16 C15 C14 124.1(3) . . ?
C17 C16 C15 118.8(4) . . ?
C17 C16 H16 122(2) . . ?
C15 C16 H16 119(2) . . ?
N6 C17 C16 123.5(4) . . ?
N6 C17 H17 119(2) . . ?
C16 C17 H17 117(2) . . ?
N6 C18 C19 123.6(4) . . ?
N6 C18 H18 114(2) . . ?
C19 C18 H18 122(2) . . ?
C18 C19 C15 119.0(3) . . ?
C18 C19 H19 120.5 . . ?
C15 C19 H19 120.5 . . ?
C10 C20 H20A 109.5 . . ?
C10 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C10 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
O5 C21 C12 118.7(3) . . ?
O5 C21 C8 122.9(3) . . ?
C12 C21 C8 118.4(3) . . ?
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
C4 N1 C1 C2 -1.1(6) . . . . ?
O4 V1 O1 C6 -84.6(3) . . . . ?
O3 V1 O1 C6 168.0(3) . . . . ?
O5 V1 O1 C6 40.9(4) . . . . ?
N3 V1 O1 C6 3.0(2) . . . . ?
N6 V1 O1 C6 83.7(2) 3 . . . ?
N1 C1 C2 C3 0.7(6) . . . . ?
C6 N2 N3 C7 172.1(3) . . . . ?
C6 N2 N3 V1 1.8(3) . . . . ?
O4 V1 N3 C7 -72.2(3) . . . . ?
O3 V1 N3 C7 131.4(5) . . . . ?
O5 V1 N3 C7 25.8(3) . . . . ?
O1 V1 N3 C7 -171.6(3) . . . . ?
N6 V1 N3 C7 106.6(3) 3 . . . ?
O4 V1 N3 N2 96.8(2) . . . . ?
O3 V1 N3 N2 -59.6(6) . . . . ?
O5 V1 N3 N2 -165.2(2) . . . . ?
O1 V1 N3 N2 -2.6(2) . . . . ?
N6 V1 N3 N2 -84.4(2) 3 . . . ?
C1 C2 C3 C5 0.1(6) . . . . ?
C1 C2 C3 C6 -177.3(4) . . . . ?
C1 N1 C4 C5 0.7(6) . . . . ?
O4 V1 O5 C21 54.0(3) . . . . ?
O3 V1 O5 C21 162.2(3) . . . . ?
O1 V1 O5 C21 -71.7(4) . . . . ?
N3 V1 O5 C21 -35.3(3) . . . . ?
N6 V1 O5 C21 -114.5(3) 3 . . . ?
C13 N4 N5 C14 177.8(3) . . . . ?
N1 C4 C5 C3 0.1(6) . . . . ?
C2 C3 C5 C4 -0.5(6) . . . . ?
C6 C3 C5 C4 177.0(4) . . . . ?
V1 O1 C6 N2 -3.4(5) . . . . ?
V1 O1 C6 C3 179.2(2) . . . . ?
N3 N2 C6 O1 0.9(5) . . . . ?
N3 N2 C6 C3 178.3(3) . . . . ?
C2 C3 C6 O1 -175.4(3) . . . . ?
C5 C3 C6 O1 7.2(5) . . . . ?
C2 C3 C6 N2 7.0(5) . . . . ?
C5 C3 C6 N2 -170.4(3) . . . . ?
N2 N3 C7 C8 -179.5(3) . . . . ?
V1 N3 C7 C8 -10.5(5) . . . . ?
N3 C7 C8 C9 173.4(4) . . . . ?
N3 C7 C8 C21 -9.2(6) . . . . ?
C21 C8 C9 C10 -0.5(6) . . . . ?
C7 C8 C9 C10 177.0(3) . . . . ?
C8 C9 C10 C11 0.1(6) . . . . ?
C8 C9 C10 C20 -177.0(3) . . . . ?
C9 C10 C11 C12 0.2(5) . . . . ?
C20 C10 C11 C12 177.4(3) . . . . ?
C10 C11 C12 C21 -0.2(6) . . . . ?
C10 C11 C12 C13 -179.4(3) . . . . ?
N5 N4 C13 C12 179.5(3) . . . . ?
C11 C12 C13 N4 -19.0(6) . . . . ?
C21 C12 C13 N4 161.7(3) . . . . ?
N4 N5 C14 O2 0.3(6) . . . . ?
N4 N5 C14 C15 179.5(3) . . . . ?
O2 C14 C15 C19 32.7(5) . . . . ?
N5 C14 C15 C19 -146.4(4) . . . . ?
O2 C14 C15 C16 -146.2(4) . . . . ?
N5 C14 C15 C16 34.6(5) . . . . ?
C19 C15 C16 C17 2.1(6) . . . . ?
C14 C15 C16 C17 -178.9(4) . . . . ?
C18 N6 C17 C16 -1.5(6) . . . . ?
V1 N6 C17 C16 180.0(3) 3_455 . . . ?
C15 C16 C17 N6 -0.7(6) . . . . ?
C17 N6 C18 C19 2.3(6) . . . . ?
V1 N6 C18 C19 -179.2(3) 3_455 . . . ?
N6 C18 C19 C15 -0.9(6) . . . . ?
C16 C15 C19 C18 -1.4(5) . . . . ?
C14 C15 C19 C18 179.6(3) . . . . ?
V1 O5 C21 C12 -151.8(3) . . . . ?
V1 O5 C21 C8 29.3(5) . . . . ?
C11 C12 C21 O5 -179.2(3) . . . . ?
C13 C12 C21 O5 0.1(5) . . . . ?
C11 C12 C21 C8 -0.2(5) . . . . ?
C13 C12 C21 C8 179.1(3) . . . . ?
C9 C8 C21 O5 179.5(3) . . . . ?
C7 C8 C21 O5 2.1(6) . . . . ?
C9 C8 C21 C12 0.5(5) . . . . ?
C7 C8 C21 C12 -176.9(3) . . . . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O3W H3WB O5W 1.00 2.01 2.965(5) 158.5 .
O4W H4WA O1W 0.80(4) 2.02(4) 2.805(5) 169(4) 2
N5 H5N O3W 0.80(5) 2.15(5) 2.930(5) 165(4) 7
O5W H5WB O1W 1.00 2.44 3.208(6) 132.3 7_565
O5W H5WA O1W 1.02 1.86 2.841(6) 160.2 3_455
_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        25.04
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.828
_refine_diff_density_min         -0.553
_refine_diff_density_rms         0.084


data_manar133
_database_code_depnum_ccdc_archive 'CCDC 924328'
#TrackingRef 'MANAR133.CIF'
_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C25 H25 N4 O6 V, 2(C H4 O)'
_chemical_formula_sum            'C27 H33 N4 O8 V'
_chemical_formula_weight         592.51
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           Triclinic
_symmetry_space_group_name_H-M   P-1
_symmetry_space_group_name_Hall  -P1
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
_cell_length_a                   7.9044(2)
_cell_length_b                   13.4380(4)
_cell_length_c                   14.3137(4)
_cell_angle_alpha                64.434(2)
_cell_angle_beta                 86.071(2)
_cell_angle_gamma                84.930(2)
_cell_volume                     1365.38(7)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    4380
_cell_measurement_theta_min      5177
_cell_measurement_theta_max      49549
_exptl_crystal_description       prism
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.09
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.441
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             620
_exptl_absorpt_coefficient_mu    0.420
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9095
_exptl_absorpt_correction_T_max  0.9651
_exptl_absorpt_process_details   'North et al., 1968'
_exptl_special_details           
;
?
;
_diffrn_ambient_temperature      100(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  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            29831
_diffrn_reflns_av_R_equivalents  0.0574
_diffrn_reflns_av_sigmaI/netI    0.0417
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         1.58
_diffrn_reflns_theta_max         25.15
_reflns_number_total             4862
_reflns_number_gt                3858
_reflns_threshold_expression     >2sigma(I)
_computing_data_collection       'Apex2, Bruker Instrument Service v2010, 1-2'
_computing_cell_refinement       
'SAINT V7.68A (Bruker: Madison, 2009 ) in Apex2 suite.'
_computing_data_reduction        
'SAINT and XPREP Version 2008/2 (Sheldrick, Bruker AXS Inc.)'
_computing_structure_solution    
'XS Version 2008/1 (George M. Sheldrick, Acta Cryst. (2008). A64, 112-122)'
_computing_structure_refinement  
'XL Version 2008/4 (George M. Sheldrick, Acta Cryst. (2008). A64, 112-122)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          
;
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ 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/[\s^2^(Fo^2^)+(0.0671P)^2^+0.4169P] where P=(Fo^2^+2Fc^2^)/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         4862
_refine_ls_number_parameters     465
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0560
_refine_ls_R_factor_gt           0.0381
_refine_ls_wR_factor_ref         0.1250
_refine_ls_wR_factor_gt          0.1010
_refine_ls_goodness_of_fit_ref   1.128
_refine_ls_restrained_S_all      1.128
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
V1 V 0.04759(6) 0.76676(4) 0.24392(3) 0.01541(15) Uani 1 1 d . . .
N1 N 0.1831(3) 1.06272(18) 0.42324(16) 0.0169(5) Uani 1 1 d . . .
C1 C 0.3940(3) 1.0069(2) 0.6657(2) 0.0174(6) Uani 1 1 d . . .
O1M O 0.1687(2) 0.65750(15) 0.34142(13) 0.0179(4) Uani 1 1 d . . .
O1 O 0.1908(2) 0.81325(15) 0.15512(13) 0.0190(4) Uani 1 1 d . . .
C1M C 0.3444(4) 0.6281(3) 0.3348(2) 0.0230(6) Uani 1 1 d . . .
H1MC H 0.384(4) 0.599(2) 0.400(3) 0.026(8) Uiso 1 1 d . . .
H1MB H 0.359(4) 0.570(3) 0.306(3) 0.039(9) Uiso 1 1 d . . .
H1MA H 0.407(4) 0.693(3) 0.284(2) 0.030(8) Uiso 1 1 d . . .
N2 N 0.2595(3) 1.0058(2) 0.51803(17) 0.0164(5) Uani 1 1 d . . .
H2N H 0.272(4) 0.937(3) 0.543(3) 0.038(10) Uiso 1 1 d . . .
C2 C 0.4136(4) 0.8930(2) 0.7195(2) 0.0210(6) Uani 1 1 d . . .
H2 H 0.371(4) 0.846(3) 0.698(2) 0.034(9) Uiso 1 1 d . . .
O2 O 0.0266(2) 0.87855(14) 0.28880(13) 0.0172(4) Uani 1 1 d . . .
O2M O -0.1673(3) 0.71183(17) 0.36444(15) 0.0196(5) Uani 1 1 d . . .
H2O H -0.189(4) 0.745(3) 0.388(3) 0.022(10) Uiso 1 1 d . . .
C2M C -0.1994(5) 0.6014(3) 0.4336(3) 0.0308(7) Uani 1 1 d . . .
H2MC H -0.184(5) 0.559(3) 0.397(3) 0.050(11) Uiso 1 1 d . . .
H2MB H -0.115(5) 0.571(3) 0.491(3) 0.048(10) Uiso 1 1 d . . .
H2MA H -0.313(5) 0.598(3) 0.466(3) 0.042(10) Uiso 1 1 d . . .
C3 C 0.4979(4) 0.8450(2) 0.8121(2) 0.0234(6) Uani 1 1 d . . .
H3 H 0.511(4) 0.762(3) 0.852(2) 0.026(8) Uiso 1 1 d . . .
N3 N -0.1435(3) 0.86834(18) 0.14246(16) 0.0152(5) Uani 1 1 d . . .
O3 O -0.0675(2) 0.66948(14) 0.20371(13) 0.0167(4) Uani 1 1 d . . .
O3M O 0.2440(3) 0.76803(16) 0.59786(15) 0.0250(5) Uani 1 1 d . . .
H3M H 0.1445 0.7522 0.6093 0.037 Uiso 1 1 calc R . .
C3M C 0.3307(5) 0.7091(3) 0.5442(3) 0.0308(7) Uani 1 1 d . . .
H3MC H 0.341(5) 0.626(3) 0.591(3) 0.053(11) Uiso 1 1 d . . .
H3MB H 0.265(5) 0.717(3) 0.490(3) 0.050(11) Uiso 1 1 d . . .
H3MA H 0.446(5) 0.738(3) 0.522(3) 0.044(10) Uiso 1 1 d . . .
O4 O 0.2786(2) 1.16818(15) 0.52681(14) 0.0207(4) Uani 1 1 d . . .
C4 C 0.5636(3) 0.9110(2) 0.8512(2) 0.0206(6) Uani 1 1 d . . .
H4 H 0.623(4) 0.878(3) 0.910(2) 0.029(8) Uiso 1 1 d . . .
N4 N -0.2564(3) 0.81467(18) 0.11209(16) 0.0168(5) Uani 1 1 d . . .
O4M O 0.0645(3) 0.30907(17) 0.37904(18) 0.0367(6) Uani 1 1 d . . .
H4M H 0.1244 0.2528 0.4108 0.055 Uiso 1 1 calc R . .
C4M C 0.1649(5) 0.3907(3) 0.3111(3) 0.0495(10) Uani 1 1 d . . .
H4M1 H 0.1207 0.4611 0.3075 0.074 Uiso 1 1 calc R . .
H4M2 H 0.1649 0.3919 0.2435 0.074 Uiso 1 1 calc R . .
H4M3 H 0.2790 0.3759 0.3350 0.074 Uiso 1 1 calc R . .
C5 C 0.5457(3) 1.0242(2) 0.7984(2) 0.0204(6) Uani 1 1 d . . .
H5 H 0.580(4) 1.071(2) 0.825(2) 0.025(8) Uiso 1 1 d . . .
C6 C 0.4612(3) 1.0725(2) 0.7058(2) 0.0184(6) Uani 1 1 d . . .
H6 H 0.447(4) 1.145(3) 0.672(2) 0.020(8) Uiso 1 1 d . . .
C7 C 0.3054(3) 1.0665(2) 0.5657(2) 0.0165(6) Uani 1 1 d . . .
C8 C 0.1428(3) 1.0031(2) 0.3802(2) 0.0171(6) Uani 1 1 d . . .
H8 H 0.159(4) 0.927(3) 0.409(2) 0.024(8) Uiso 1 1 d . . .
C9 C 0.0678(3) 1.0556(2) 0.27765(19) 0.0156(6) Uani 1 1 d . . .
C10 C 0.0588(3) 1.1695(2) 0.2195(2) 0.0172(6) Uani 1 1 d . . .
H10 H 0.094(4) 1.214(2) 0.250(2) 0.023(8) Uiso 1 1 d . . .
C11 C -0.0033(3) 1.2204(2) 0.12045(19) 0.0161(6) Uani 1 1 d . . .
C12 C -0.0693(3) 1.1539(2) 0.0816(2) 0.0169(6) Uani 1 1 d . . .
H12 H -0.123(4) 1.189(2) 0.015(2) 0.030(8) Uiso 1 1 d . . .
C13 C -0.0638(3) 1.0386(2) 0.13730(19) 0.0162(6) Uani 1 1 d . . .
C14 C 0.0130(3) 0.9883(2) 0.23457(19) 0.0148(5) Uani 1 1 d . . .
C15 C 0.0010(4) 1.3435(2) 0.0575(2) 0.0227(6) Uani 1 1 d . . .
H15A H -0.0811 1.3807 0.0861 0.034 Uiso 1 1 calc R . .
H15B H -0.0254 1.3624 -0.0128 0.034 Uiso 1 1 calc R . .
H15C H 0.1123 1.3659 0.0592 0.034 Uiso 1 1 calc R . .
C16 C -0.1555(3) 0.9747(2) 0.10073(19) 0.0159(6) Uani 1 1 d . . .
H16 H -0.240(4) 1.015(2) 0.043(2) 0.025(8) Uiso 1 1 d . . .
C17 C -0.2070(3) 0.7101(2) 0.15152(19) 0.0158(6) Uani 1 1 d . . .
C18 C -0.3159(3) 0.6317(2) 0.14089(19) 0.0162(6) Uani 1 1 d . . .
C19 C -0.4688(4) 0.6701(3) 0.0902(2) 0.0211(6) Uani 1 1 d . . .
H19 H -0.502(4) 0.742(3) 0.064(2) 0.030(9) Uiso 1 1 d . . .
C20 C -0.5714(4) 0.5975(3) 0.0809(2) 0.0275(7) Uani 1 1 d . . .
H20 H -0.681(4) 0.626(3) 0.045(2) 0.036(9) Uiso 1 1 d . . .
C21 C -0.5236(4) 0.4856(3) 0.1235(2) 0.0274(7) Uani 1 1 d . . .
H21 H -0.591(4) 0.436(3) 0.117(2) 0.033(8) Uiso 1 1 d . . .
C22 C -0.3750(4) 0.4461(3) 0.1760(2) 0.0254(7) Uani 1 1 d . . .
H22 H -0.341(4) 0.375(3) 0.201(2) 0.026(8) Uiso 1 1 d . . .
C23 C -0.2710(4) 0.5198(2) 0.1838(2) 0.0206(6) Uani 1 1 d . . .
H23 H -0.172(4) 0.493(2) 0.214(2) 0.019(7) Uiso 1 1 d . . .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
V1 0.0168(3) 0.0163(3) 0.0150(2) -0.0082(2) -0.00382(18) -0.00024(18)
N1 0.0166(11) 0.0226(13) 0.0142(11) -0.0102(10) -0.0022(9) -0.0013(9)
C1 0.0132(13) 0.0240(15) 0.0183(13) -0.0124(12) 0.0016(11) -0.0018(11)
O1M 0.0169(10) 0.0193(10) 0.0190(9) -0.0094(8) -0.0058(8) 0.0012(8)
O1 0.0179(10) 0.0224(10) 0.0185(9) -0.0101(8) -0.0036(8) -0.0010(8)
C1M 0.0188(15) 0.0247(17) 0.0254(16) -0.0106(14) -0.0062(13) 0.0024(12)
N2 0.0191(12) 0.0173(13) 0.0149(11) -0.0085(10) -0.0040(9) -0.0006(10)
C2 0.0226(15) 0.0247(16) 0.0198(14) -0.0129(13) -0.0014(12) -0.0038(12)
O2 0.0220(10) 0.0168(10) 0.0149(9) -0.0082(8) -0.0037(8) -0.0026(8)
O2M 0.0260(11) 0.0150(11) 0.0200(10) -0.0098(9) 0.0012(8) -0.0008(8)
C2M 0.040(2) 0.0188(17) 0.0289(17) -0.0067(14) 0.0092(16) -0.0041(14)
C3 0.0262(16) 0.0207(16) 0.0221(15) -0.0076(13) -0.0043(12) -0.0006(12)
N3 0.0157(11) 0.0178(13) 0.0137(11) -0.0078(9) -0.0026(9) -0.0021(9)
O3 0.0173(10) 0.0177(10) 0.0179(9) -0.0099(8) -0.0058(8) 0.0010(7)
O3M 0.0305(11) 0.0222(11) 0.0252(10) -0.0123(9) -0.0032(9) -0.0038(9)
C3M 0.0348(19) 0.032(2) 0.0278(17) -0.0146(15) 0.0012(15) -0.0035(15)
O4 0.0269(11) 0.0178(11) 0.0198(10) -0.0099(8) -0.0046(8) -0.0011(8)
C4 0.0168(14) 0.0285(17) 0.0164(14) -0.0096(13) -0.0049(12) 0.0017(12)
N4 0.0185(12) 0.0189(13) 0.0151(11) -0.0087(10) -0.0047(9) -0.0016(9)
O4M 0.0276(12) 0.0232(12) 0.0501(14) -0.0058(11) -0.0102(11) -0.0012(9)
C4M 0.046(2) 0.041(2) 0.048(2) -0.0035(18) -0.0129(18) -0.0160(18)
C5 0.0167(14) 0.0294(17) 0.0215(14) -0.0164(13) -0.0012(11) -0.0044(12)
C6 0.0166(14) 0.0205(16) 0.0205(14) -0.0109(13) -0.0010(11) -0.0007(12)
C7 0.0132(13) 0.0233(16) 0.0167(13) -0.0120(12) 0.0026(11) -0.0037(11)
C8 0.0158(14) 0.0186(16) 0.0179(13) -0.0090(12) -0.0011(11) 0.0004(11)
C9 0.0136(13) 0.0203(15) 0.0154(13) -0.0102(11) -0.0011(10) -0.0002(11)
C10 0.0151(14) 0.0201(15) 0.0201(14) -0.0122(12) 0.0004(11) -0.0008(11)
C11 0.0159(14) 0.0152(14) 0.0173(13) -0.0077(11) 0.0001(11) 0.0010(11)
C12 0.0165(14) 0.0198(15) 0.0134(13) -0.0069(12) 0.0005(11) 0.0010(11)
C13 0.0167(14) 0.0194(15) 0.0145(13) -0.0096(11) 0.0013(11) -0.0007(11)
C14 0.0132(13) 0.0159(14) 0.0152(13) -0.0070(11) 0.0013(10) 0.0004(10)
C15 0.0267(16) 0.0217(16) 0.0208(14) -0.0098(12) -0.0010(12) -0.0031(12)
C16 0.0178(14) 0.0172(15) 0.0136(13) -0.0080(11) 0.0006(11) 0.0010(11)
C17 0.0167(14) 0.0211(15) 0.0116(12) -0.0089(11) -0.0003(11) -0.0006(11)
C18 0.0198(14) 0.0190(15) 0.0125(12) -0.0092(11) -0.0009(11) -0.0020(11)
C19 0.0236(15) 0.0191(16) 0.0218(14) -0.0096(13) -0.0043(12) -0.0003(12)
C20 0.0248(17) 0.0295(18) 0.0315(16) -0.0148(14) -0.0114(14) -0.0008(13)
C21 0.0293(17) 0.0285(18) 0.0305(16) -0.0167(14) -0.0025(13) -0.0107(14)
C22 0.0323(17) 0.0185(17) 0.0275(16) -0.0111(14) -0.0063(13) -0.0014(13)
C23 0.0190(15) 0.0234(16) 0.0219(14) -0.0118(12) -0.0063(12) 0.0015(12)
_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 O1 1.5907(18) . ?
V1 O1M 1.7848(18) . ?
V1 O2 1.8631(17) . ?
V1 O3 1.9489(17) . ?
V1 N3 2.117(2) . ?
V1 O2M 2.264(2) . ?
N1 C8 1.274(3) . ?
N1 N2 1.387(3) . ?
C1 C2 1.384(4) . ?
C1 C6 1.397(4) . ?
C1 C7 1.494(4) . ?
O1M C1M 1.418(3) . ?
C1M H1MC 0.90(3) . ?
C1M H1MB 1.03(3) . ?
C1M H1MA 1.01(3) . ?
N2 C7 1.351(3) . ?
N2 H2N 0.84(3) . ?
C2 C3 1.388(4) . ?
C2 H2 0.90(3) . ?
O2 C14 1.336(3) . ?
O2M C2M 1.418(4) . ?
O2M H2O 0.66(3) . ?
C2M H2MC 0.92(4) . ?
C2M H2MB 1.01(4) . ?
C2M H2MA 0.98(4) . ?
C3 C4 1.386(4) . ?
C3 H3 1.01(3) . ?
N3 C16 1.286(3) . ?
N3 N4 1.394(3) . ?
O3 C17 1.314(3) . ?
O3M C3M 1.429(4) . ?
O3M H3M 0.8200 . ?
C3M H3MC 1.02(4) . ?
C3M H3MB 0.92(4) . ?
C3M H3MA 0.99(4) . ?
O4 C7 1.237(3) . ?
C4 C5 1.375(4) . ?
C4 H4 0.91(3) . ?
N4 C17 1.302(3) . ?
O4M C4M 1.381(4) . ?
O4M H4M 0.8200 . ?
C4M H4M1 0.9600 . ?
C4M H4M2 0.9600 . ?
C4M H4M3 0.9600 . ?
C5 C6 1.388(4) . ?
C5 H5 0.93(3) . ?
C6 H6 0.88(3) . ?
C8 C9 1.468(4) . ?
C8 H8 0.92(3) . ?
C9 C10 1.390(4) . ?
C9 C14 1.404(3) . ?
C10 C11 1.385(4) . ?
C10 H10 0.95(3) . ?
C11 C12 1.390(4) . ?
C11 C15 1.506(4) . ?
C12 C13 1.402(4) . ?
C12 H12 0.97(3) . ?
C13 C14 1.412(4) . ?
C13 C16 1.445(4) . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C16 H16 1.03(3) . ?
C17 C18 1.480(3) . ?
C18 C23 1.379(4) . ?
C18 C19 1.393(4) . ?
C19 C20 1.376(4) . ?
C19 H19 0.90(3) . ?
C20 C21 1.384(4) . ?
C20 H20 0.99(3) . ?
C21 C22 1.375(4) . ?
C21 H21 0.93(3) . ?
C22 C23 1.387(4) . ?
C22 H22 0.88(3) . ?
C23 H23 0.89(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
O1 V1 O1M 100.04(9) . . ?
O1 V1 O2 99.93(9) . . ?
O1M V1 O2 103.84(8) . . ?
O1 V1 O3 103.04(8) . . ?
O1M V1 O3 94.85(8) . . ?
O2 V1 O3 147.23(8) . . ?
O1 V1 N3 91.36(9) . . ?
O1M V1 N3 165.84(8) . . ?
O2 V1 N3 82.21(8) . . ?
O3 V1 N3 74.24(8) . . ?
O1 V1 O2M 175.99(9) . . ?
O1M V1 O2M 83.79(8) . . ?
O2 V1 O2M 77.88(8) . . ?
O3 V1 O2M 77.68(8) . . ?
N3 V1 O2M 85.02(8) . . ?
C8 N1 N2 115.4(2) . . ?
C2 C1 C6 119.0(3) . . ?
C2 C1 C7 124.5(2) . . ?
C6 C1 C7 116.5(2) . . ?
C1M O1M V1 126.69(17) . . ?
O1M C1M H1MC 107.5(19) . . ?
O1M C1M H1MB 108.8(18) . . ?
H1MC C1M H1MB 110(3) . . ?
O1M C1M H1MA 110.9(18) . . ?
H1MC C1M H1MA 114(2) . . ?
H1MB C1M H1MA 106(2) . . ?
C7 N2 N1 117.1(2) . . ?
C7 N2 H2N 124(2) . . ?
N1 N2 H2N 118(2) . . ?
C1 C2 C3 120.4(3) . . ?
C1 C2 H2 123(2) . . ?
C3 C2 H2 116(2) . . ?
C14 O2 V1 130.26(15) . . ?
C2M O2M V1 126.47(19) . . ?
C2M O2M H2O 109(3) . . ?
V1 O2M H2O 116(3) . . ?
O2M C2M H2MC 108(2) . . ?
O2M C2M H2MB 111(2) . . ?
H2MC C2M H2MB 107(3) . . ?
O2M C2M H2MA 111(2) . . ?
H2MC C2M H2MA 113(3) . . ?
H2MB C2M H2MA 107(3) . . ?
C4 C3 C2 120.0(3) . . ?
C4 C3 H3 119.5(16) . . ?
C2 C3 H3 120.5(16) . . ?
C16 N3 N4 117.8(2) . . ?
C16 N3 V1 125.53(17) . . ?
N4 N3 V1 116.43(15) . . ?
C17 O3 V1 117.42(16) . . ?
C3M O3M H3M 109.5 . . ?
O3M C3M H3MC 111(2) . . ?
O3M C3M H3MB 108(2) . . ?
H3MC C3M H3MB 106(3) . . ?
O3M C3M H3MA 108(2) . . ?
H3MC C3M H3MA 110(3) . . ?
H3MB C3M H3MA 114(3) . . ?
C5 C4 C3 120.2(3) . . ?
C5 C4 H4 121.2(19) . . ?
C3 C4 H4 118.5(19) . . ?
C17 N4 N3 107.6(2) . . ?
C4M O4M H4M 109.5 . . ?
O4M C4M H4M1 109.5 . . ?
O4M C4M H4M2 109.5 . . ?
H4M1 C4M H4M2 109.5 . . ?
O4M C4M H4M3 109.5 . . ?
H4M1 C4M H4M3 109.5 . . ?
H4M2 C4M H4M3 109.5 . . ?
C4 C5 C6 119.9(3) . . ?
C4 C5 H5 122.4(19) . . ?
C6 C5 H5 117.5(19) . . ?
C5 C6 C1 120.5(3) . . ?
C5 C6 H6 120.3(18) . . ?
C1 C6 H6 119.3(18) . . ?
O4 C7 N2 121.3(2) . . ?
O4 C7 C1 120.9(2) . . ?
N2 C7 C1 117.7(2) . . ?
N1 C8 C9 119.7(3) . . ?
N1 C8 H8 124.2(18) . . ?
C9 C8 H8 116.0(18) . . ?
C10 C9 C14 119.1(2) . . ?
C10 C9 C8 121.9(2) . . ?
C14 C9 C8 118.9(2) . . ?
C11 C10 C9 122.8(2) . . ?
C11 C10 H10 119.2(18) . . ?
C9 C10 H10 118.0(17) . . ?
C10 C11 C12 117.6(2) . . ?
C10 C11 C15 120.9(2) . . ?
C12 C11 C15 121.5(2) . . ?
C11 C12 C13 121.6(2) . . ?
C11 C12 H12 118.4(18) . . ?
C13 C12 H12 120.0(17) . . ?
C12 C13 C14 119.4(2) . . ?
C12 C13 C16 119.3(2) . . ?
C14 C13 C16 120.8(2) . . ?
O2 C14 C9 119.3(2) . . ?
O2 C14 C13 121.6(2) . . ?
C9 C14 C13 119.0(2) . . ?
C11 C15 H15A 109.5 . . ?
C11 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C11 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
N3 C16 C13 122.5(2) . . ?
N3 C16 H16 118.6(16) . . ?
C13 C16 H16 118.7(16) . . ?
N4 C17 O3 123.3(2) . . ?
N4 C17 C18 118.8(2) . . ?
O3 C17 C18 117.9(2) . . ?
C23 C18 C19 119.2(2) . . ?
C23 C18 C17 120.8(2) . . ?
C19 C18 C17 120.0(2) . . ?
C20 C19 C18 120.3(3) . . ?
C20 C19 H19 119(2) . . ?
C18 C19 H19 121(2) . . ?
C19 C20 C21 119.8(3) . . ?
C19 C20 H20 119.2(18) . . ?
C21 C20 H20 120.9(18) . . ?
C22 C21 C20 120.6(3) . . ?
C22 C21 H21 119(2) . . ?
C20 C21 H21 121(2) . . ?
C21 C22 C23 119.3(3) . . ?
C21 C22 H22 121.5(19) . . ?
C23 C22 H22 119(2) . . ?
C18 C23 C22 120.8(3) . . ?
C18 C23 H23 120.9(18) . . ?
C22 C23 H23 118.2(18) . . ?
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
O1 V1 O1M C1M 1.0(2) . . . . ?
O2 V1 O1M C1M -101.9(2) . . . . ?
O3 V1 O1M C1M 105.2(2) . . . . ?
N3 V1 O1M C1M 144.1(3) . . . . ?
O2M V1 O1M C1M -177.8(2) . . . . ?
C8 N1 N2 C7 179.5(2) . . . . ?
C6 C1 C2 C3 0.4(4) . . . . ?
C7 C1 C2 C3 -180.0(3) . . . . ?
O1 V1 O2 C14 46.7(2) . . . . ?
O1M V1 O2 C14 149.7(2) . . . . ?
O3 V1 O2 C14 -87.4(2) . . . . ?
N3 V1 O2 C14 -43.3(2) . . . . ?
O2M V1 O2 C14 -129.9(2) . . . . ?
O1 V1 O2M C2M 158.5(11) . . . . ?
O1M V1 O2M C2M -38.6(2) . . . . ?
O2 V1 O2M C2M -144.2(2) . . . . ?
O3 V1 O2M C2M 57.8(2) . . . . ?
N3 V1 O2M C2M 132.7(2) . . . . ?
C1 C2 C3 C4 -0.2(4) . . . . ?
O1 V1 N3 C16 -64.1(2) . . . . ?
O1M V1 N3 C16 152.2(3) . . . . ?
O2 V1 N3 C16 35.8(2) . . . . ?
O3 V1 N3 C16 -167.2(2) . . . . ?
O2M V1 N3 C16 114.2(2) . . . . ?
O1 V1 N3 N4 110.16(17) . . . . ?
O1M V1 N3 N4 -33.6(4) . . . . ?
O2 V1 N3 N4 -150.00(17) . . . . ?
O3 V1 N3 N4 6.99(15) . . . . ?
O2M V1 N3 N4 -71.59(16) . . . . ?
O1 V1 O3 C17 -96.67(18) . . . . ?
O1M V1 O3 C17 161.84(17) . . . . ?
O2 V1 O3 C17 36.7(2) . . . . ?
N3 V1 O3 C17 -8.96(16) . . . . ?
O2M V1 O3 C17 79.28(17) . . . . ?
C2 C3 C4 C5 0.0(4) . . . . ?
C16 N3 N4 C17 171.0(2) . . . . ?
V1 N3 N4 C17 -3.7(2) . . . . ?
C3 C4 C5 C6 0.1(4) . . . . ?
C4 C5 C6 C1 0.0(4) . . . . ?
C2 C1 C6 C5 -0.3(4) . . . . ?
C7 C1 C6 C5 -180.0(2) . . . . ?
N1 N2 C7 O4 0.8(4) . . . . ?
N1 N2 C7 C1 -177.6(2) . . . . ?
C2 C1 C7 O4 173.2(2) . . . . ?
C6 C1 C7 O4 -7.2(4) . . . . ?
C2 C1 C7 N2 -8.5(4) . . . . ?
C6 C1 C7 N2 171.2(2) . . . . ?
N2 N1 C8 C9 -177.4(2) . . . . ?
N1 C8 C9 C10 8.4(4) . . . . ?
N1 C8 C9 C14 -175.5(2) . . . . ?
C14 C9 C10 C11 0.5(4) . . . . ?
C8 C9 C10 C11 176.5(2) . . . . ?
C9 C10 C11 C12 4.4(4) . . . . ?
C9 C10 C11 C15 -175.6(2) . . . . ?
C10 C11 C12 C13 -4.1(4) . . . . ?
C15 C11 C12 C13 175.9(2) . . . . ?
C11 C12 C13 C14 -1.1(4) . . . . ?
C11 C12 C13 C16 171.1(2) . . . . ?
V1 O2 C14 C9 -153.77(19) . . . . ?
V1 O2 C14 C13 29.8(3) . . . . ?
C10 C9 C14 O2 177.8(2) . . . . ?
C8 C9 C14 O2 1.6(4) . . . . ?
C10 C9 C14 C13 -5.7(4) . . . . ?
C8 C9 C14 C13 178.1(2) . . . . ?
C12 C13 C14 O2 -177.6(2) . . . . ?
C16 C13 C14 O2 10.4(4) . . . . ?
C12 C13 C14 C9 6.0(4) . . . . ?
C16 C13 C14 C9 -166.0(2) . . . . ?
N4 N3 C16 C13 170.3(2) . . . . ?
V1 N3 C16 C13 -15.6(3) . . . . ?
C12 C13 C16 N3 173.5(2) . . . . ?
C14 C13 C16 N3 -14.5(4) . . . . ?
N3 N4 C17 O3 -4.3(3) . . . . ?
N3 N4 C17 C18 173.3(2) . . . . ?
V1 O3 C17 N4 11.0(3) . . . . ?
V1 O3 C17 C18 -166.58(17) . . . . ?
N4 C17 C18 C23 -178.2(2) . . . . ?
O3 C17 C18 C23 -0.5(4) . . . . ?
N4 C17 C18 C19 -0.5(4) . . . . ?
O3 C17 C18 C19 177.2(2) . . . . ?
C23 C18 C19 C20 -1.6(4) . . . . ?
C17 C18 C19 C20 -179.4(3) . . . . ?
C18 C19 C20 C21 0.9(4) . . . . ?
C19 C20 C21 C22 0.6(5) . . . . ?
C20 C21 C22 C23 -1.5(5) . . . . ?
C19 C18 C23 C22 0.7(4) . . . . ?
C17 C18 C23 C22 178.4(2) . . . . ?
C21 C22 C23 C18 0.9(4) . . . . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N2 H2N O3M 0.84(3) 2.08(4) 2.904(3) 167(3) .
O2M H2O O4 0.66(3) 2.09(3) 2.743(3) 173(4) 2_576
O3M H3M O4M 0.82 1.88 2.677(3) 165.5 2_566
O4M H4M O4 0.82 1.99 2.718(3) 148.6 1_545
O4M H4M N1 0.82 2.49 3.157(3) 139.8 1_545
_diffrn_measured_fraction_theta_max 0.994
_diffrn_reflns_theta_full        25.15
_diffrn_measured_fraction_theta_full 0.994
_refine_diff_density_max         0.707
_refine_diff_density_min         -0.403
_refine_diff_density_rms         0.111