# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2015

####################################################################### 
# 
# 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_b
_database_code_depnum_ccdc_archive 'CCDC 1056936'
_audit_update_record             
;
2015-10-01 deposited with the CCDC.
2015-11-16 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         C14H15N2O12V
_chemical_formula_sum            'C14 H15 N2 O12 V'
_chemical_formula_weight         454.22

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

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

_cell_length_a                   8.540(2)
_cell_length_b                   9.813(3)
_cell_length_c                   11.707(3)
_cell_angle_alpha                82.404(4)
_cell_angle_beta                 73.547(4)
_cell_angle_gamma                68.028(4)
_cell_volume                     872.2(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    1199
_cell_measurement_theta_min      2.66
_cell_measurement_theta_max      25.76

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.05
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.730
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             464
_exptl_absorpt_coefficient_mu    0.642
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9269
_exptl_absorpt_correction_T_max  0.9686
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(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         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0
_diffrn_reflns_number            4712
_diffrn_reflns_av_R_equivalents  0.0360
_diffrn_reflns_av_nuetI/netI     0.0743
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         1.81
_diffrn_reflns_theta_max         25.95
_reflns_number_total             3313
_reflns_number_gt                2386
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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 > 2sigma(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)+(0.0710P)²+0.7317P] 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         3313
_refine_ls_number_parameters     262
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0835
_refine_ls_R_factor_gt           0.0555
_refine_ls_wR_factor_ref         0.1534
_refine_ls_wR_factor_gt          0.1371
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_restrained_S_all      1.049
_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
O2W O 0.6033(4) 0.0254(3) 0.1615(2) 0.0372(8) Uani 1 1 d . . .
H2WB H 0.5134 0.0054 0.1650 0.056 Uiso 1 1 d R . .
H2WC H 0.6149 0.0877 0.1050 0.056 Uiso 1 1 d R . .
O10 O 0.7194(4) 0.3160(3) 0.4305(2) 0.0292(7) Uani 1 1 d . . .
H10A H 0.8105 0.2992 0.4692 0.044 Uiso 1 1 d R . .
H10B H 0.6639 0.4198 0.4179 0.044 Uiso 1 1 d R . .
V1 V 0.53624(9) 0.23088(7) 0.53769(6) 0.0223(2) Uani 1 1 d . . .
O3 O 0.4330(4) 0.3996(3) 0.6550(2) 0.0294(7) Uani 1 1 d . . .
O1 O 0.7205(4) 0.0242(3) 0.4948(2) 0.0270(6) Uani 1 1 d . . .
O5 O 0.4785(4) 0.1866(3) 0.3832(2) 0.0302(7) Uani 1 1 d . . .
O2 O 0.9470(4) -0.1683(3) 0.5324(3) 0.0319(7) Uani 1 1 d . . .
N1 N 0.6802(4) 0.1660(4) 0.6691(3) 0.0245(7) Uani 1 1 d . . .
O6 O 0.3412(4) 0.3956(3) 0.4690(3) 0.0334(7) Uani 1 1 d . . .
C3 C 0.3623(5) 0.3121(4) 0.3880(3) 0.0255(9) Uani 1 1 d . . .
O7 O 0.3559(4) 0.1359(4) 0.0116(3) 0.0531(10) Uani 1 1 d D . .
C5 C 0.8149(5) 0.0386(4) 0.6603(4) 0.0254(9) Uani 1 1 d . . .
N2 N 0.2792(4) 0.2786(4) 0.2137(3) 0.0266(8) Uani 1 1 d . . .
O4 O 0.4407(5) 0.4971(4) 0.8157(3) 0.0510(10) Uani 1 1 d . . .
C10 C 0.2442(5) 0.3648(4) 0.3048(3) 0.0247(9) Uani 1 1 d . . .
O8 O 0.0880(5) 0.2420(4) -0.0065(3) 0.0512(9) Uani 1 1 d . . .
H8A H 0.1235 0.1846 -0.0608 0.077 Uiso 1 1 calc R . .
C11 C 0.1031(5) 0.4970(5) 0.3275(4) 0.0304(10) Uani 1 1 d . . .
H11 H 0.0868 0.5551 0.3895 0.037 Uiso 1 1 calc R . .
O9 O 0.3530(4) 0.1419(3) 0.6369(2) 0.0268(6) Uani 1 1 d . . .
H9A H 0.3851 0.0966 0.7088 0.040 Uiso 1 1 d R . .
H9B H 0.3492 0.0693 0.5913 0.040 Uiso 1 1 d R . .
C14 C 0.1656(5) 0.3230(5) 0.1446(4) 0.0283(9) Uani 1 1 d . . .
C1 C 0.8354(5) -0.0470(4) 0.5559(3) 0.0241(9) Uani 1 1 d . . .
C13 C 0.0184(6) 0.4506(5) 0.1644(4) 0.0370(11) Uani 1 1 d . . .
H13 H -0.0588 0.4753 0.1163 0.044 Uiso 1 1 calc R . .
C9 C 0.6440(6) 0.2591(5) 0.7547(4) 0.0294(9) Uani 1 1 d . . .
C6 C 0.9218(6) 0.0000(5) 0.7377(4) 0.0333(10) Uani 1 1 d . . .
H6 H 1.0163 -0.0881 0.7302 0.040 Uiso 1 1 calc R . .
C4 C 0.2085(4) 0.2240(4) 0.0405(4) 0.0353(10) Uani 1 1 d D . .
C12 C -0.0125(6) 0.5401(5) 0.2557(4) 0.0352(10) Uani 1 1 d . . .
H12 H -0.1084 0.6272 0.2689 0.042 Uiso 1 1 calc R . .
C2 C 0.4936(6) 0.3975(5) 0.7454(4) 0.0308(10) Uani 1 1 d . . .
C7 C 0.8844(7) 0.0959(5) 0.8262(4) 0.0428(12) Uani 1 1 d . . .
H7 H 0.9549 0.0726 0.8788 0.051 Uiso 1 1 calc R . .
C8 C 0.7427(7) 0.2266(5) 0.8373(4) 0.0396(11) Uani 1 1 d . . .
H8 H 0.7147 0.2905 0.8980 0.048 Uiso 1 1 calc R . .
O1W O 0.7747(5) 0.2147(4) 0.1282(3) 0.0571(10) Uani 1 1 d . . .
H1WA H 0.8854 0.1802 0.1138 0.086 Uiso 1 1 d R . .
H1WC H 0.7419 0.3010 0.0978 0.086 Uiso 1 1 d R . .


_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
O2W H2WB 0.8501 . ?
O2W H2WC 0.8499 . ?
O10 V1 2.076(3) . ?
O10 H10A 0.9600 . ?
O10 H10B 0.9599 . ?
V1 O3 2.056(3) . ?
V1 O1 2.068(3) . ?
V1 O9 2.070(3) . ?
V1 O6 2.106(3) . ?
V1 N1 2.123(3) . ?
V1 O5 2.139(3) . ?
O3 C2 1.298(5) . ?
O1 C1 1.310(5) . ?
O5 C3 1.255(5) . ?
O2 C1 1.221(5) . ?
N1 C5 1.338(5) . ?
N1 C9 1.338(5) . ?
O6 C3 1.266(5) . ?
C3 C10 1.505(6) . ?
O7 C4 1.212(2) . ?
C5 C6 1.384(6) . ?
C5 C1 1.507(6) . ?
N2 C10 1.346(5) . ?
N2 C14 1.350(5) . ?
O4 C2 1.229(5) . ?
C10 C11 1.395(6) . ?
O8 C4 1.245(5) . ?
O8 H8A 0.8200 . ?
C11 C12 1.386(6) . ?
C11 H11 0.9300 . ?
O9 H9A 0.9601 . ?
O9 H9B 0.9600 . ?
C14 C13 1.391(6) . ?
C14 C4 1.536(6) . ?
C13 C12 1.379(6) . ?
C13 H13 0.9300 . ?
C9 C8 1.388(6) . ?
C9 C2 1.496(6) . ?
C6 C7 1.381(6) . ?
C6 H6 0.9300 . ?
C12 H12 0.9300 . ?
C7 C8 1.385(7) . ?
C7 H7 0.9300 . ?
C8 H8 0.9300 . ?
O1W H1WA 0.8500 . ?
O1W H1WC 0.8500 . ?

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
H2WB O2W H2WC 109.5 . . ?
V1 O10 H10A 109.3 . . ?
V1 O10 H10B 109.4 . . ?
H10A O10 H10B 109.5 . . ?
O3 V1 O1 146.18(11) . . ?
O3 V1 O9 89.39(11) . . ?
O1 V1 O9 91.52(11) . . ?
O3 V1 O10 93.06(12) . . ?
O1 V1 O10 87.33(11) . . ?
O9 V1 O10 177.10(11) . . ?
O3 V1 O6 74.66(11) . . ?
O1 V1 O6 139.13(11) . . ?
O9 V1 O6 89.91(12) . . ?
O10 V1 O6 89.23(12) . . ?
O3 V1 N1 73.20(12) . . ?
O1 V1 N1 72.99(12) . . ?
O9 V1 N1 92.12(12) . . ?
O10 V1 N1 90.09(12) . . ?
O6 V1 N1 147.77(12) . . ?
O3 V1 O5 135.66(11) . . ?
O1 V1 O5 78.12(11) . . ?
O9 V1 O5 86.82(11) . . ?
O10 V1 O5 90.34(12) . . ?
O6 V1 O5 61.18(11) . . ?
N1 V1 O5 151.05(12) . . ?
C2 O3 V1 123.1(3) . . ?
C1 O1 V1 123.1(2) . . ?
C3 O5 V1 89.8(2) . . ?
C5 N1 C9 120.4(4) . . ?
C5 N1 V1 120.1(3) . . ?
C9 N1 V1 119.3(3) . . ?
C3 O6 V1 91.0(2) . . ?
O5 C3 O6 118.0(4) . . ?
O5 C3 C10 123.0(4) . . ?
O6 C3 C10 119.0(3) . . ?
N1 C5 C6 121.4(4) . . ?
N1 C5 C1 111.7(3) . . ?
C6 C5 C1 126.9(4) . . ?
C10 N2 C14 116.6(3) . . ?
N2 C10 C11 123.7(4) . . ?
N2 C10 C3 117.5(3) . . ?
C11 C10 C3 118.9(4) . . ?
C4 O8 H8A 109.5 . . ?
C12 C11 C10 118.7(4) . . ?
C12 C11 H11 120.6 . . ?
C10 C11 H11 120.6 . . ?
V1 O9 H9A 109.4 . . ?
V1 O9 H9B 109.4 . . ?
H9A O9 H9B 109.5 . . ?
N2 C14 C13 123.0(4) . . ?
N2 C14 C4 115.9(3) . . ?
C13 C14 C4 121.1(4) . . ?
O2 C1 O1 124.8(4) . . ?
O2 C1 C5 123.1(4) . . ?
O1 C1 C5 112.1(3) . . ?
C12 C13 C14 119.6(4) . . ?
C12 C13 H13 120.2 . . ?
C14 C13 H13 120.2 . . ?
N1 C9 C8 121.5(4) . . ?
N1 C9 C2 111.8(4) . . ?
C8 C9 C2 126.6(4) . . ?
C7 C6 C5 118.2(4) . . ?
C7 C6 H6 120.9 . . ?
C5 C6 H6 120.9 . . ?
O7 C4 O8 126.1(4) . . ?
O7 C4 C14 117.2(4) . . ?
O8 C4 C14 116.7(3) . . ?
C13 C12 C11 118.3(4) . . ?
C13 C12 H12 120.8 . . ?
C11 C12 H12 120.8 . . ?
O4 C2 O3 125.7(4) . . ?
O4 C2 C9 121.7(4) . . ?
O3 C2 C9 112.6(3) . . ?
C6 C7 C8 120.6(4) . . ?
C6 C7 H7 119.7 . . ?
C8 C7 H7 119.7 . . ?
C7 C8 C9 117.8(4) . . ?
C7 C8 H8 121.1 . . ?
C9 C8 H8 121.1 . . ?
H1WA O1W H1WC 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
O1 V1 O3 C2 2.3(4) . . . . ?
O9 V1 O3 C2 94.1(3) . . . . ?
O10 V1 O3 C2 -87.5(3) . . . . ?
O6 V1 O3 C2 -175.8(3) . . . . ?
N1 V1 O3 C2 1.7(3) . . . . ?
O5 V1 O3 C2 178.9(3) . . . . ?
O3 V1 O1 C1 -2.6(4) . . . . ?
O9 V1 O1 C1 -93.8(3) . . . . ?
O10 V1 O1 C1 88.9(3) . . . . ?
O6 V1 O1 C1 174.6(3) . . . . ?
N1 V1 O1 C1 -2.0(3) . . . . ?
O5 V1 O1 C1 179.8(3) . . . . ?
O3 V1 O5 C3 4.6(3) . . . . ?
O1 V1 O5 C3 -177.3(3) . . . . ?
O9 V1 O5 C3 90.5(3) . . . . ?
O10 V1 O5 C3 -90.1(2) . . . . ?
O6 V1 O5 C3 -1.1(2) . . . . ?
N1 V1 O5 C3 179.1(3) . . . . ?
O3 V1 N1 C5 -177.1(3) . . . . ?
O1 V1 N1 C5 3.3(3) . . . . ?
O9 V1 N1 C5 94.2(3) . . . . ?
O10 V1 N1 C5 -83.9(3) . . . . ?
O6 V1 N1 C5 -172.6(3) . . . . ?
O5 V1 N1 C5 7.0(5) . . . . ?
O3 V1 N1 C9 -2.6(3) . . . . ?
O1 V1 N1 C9 177.8(3) . . . . ?
O9 V1 N1 C9 -91.3(3) . . . . ?
O10 V1 N1 C9 90.6(3) . . . . ?
O6 V1 N1 C9 1.9(4) . . . . ?
O5 V1 N1 C9 -178.5(3) . . . . ?
O3 V1 O6 C3 -174.7(3) . . . . ?
O1 V1 O6 C3 6.9(3) . . . . ?
O9 V1 O6 C3 -85.3(2) . . . . ?
O10 V1 O6 C3 92.0(2) . . . . ?
N1 V1 O6 C3 -179.1(3) . . . . ?
O5 V1 O6 C3 1.1(2) . . . . ?
V1 O5 C3 O6 1.9(4) . . . . ?
V1 O5 C3 C10 -175.9(4) . . . . ?
V1 O6 C3 O5 -1.9(4) . . . . ?
V1 O6 C3 C10 176.0(3) . . . . ?
C9 N1 C5 C6 -0.9(6) . . . . ?
V1 N1 C5 C6 173.5(3) . . . . ?
C9 N1 C5 C1 -178.3(3) . . . . ?
V1 N1 C5 C1 -3.9(5) . . . . ?
C14 N2 C10 C11 -2.4(6) . . . . ?
C14 N2 C10 C3 176.0(4) . . . . ?
O5 C3 C10 N2 -7.6(6) . . . . ?
O6 C3 C10 N2 174.6(4) . . . . ?
O5 C3 C10 C11 170.9(4) . . . . ?
O6 C3 C10 C11 -6.9(6) . . . . ?
N2 C10 C11 C12 2.8(7) . . . . ?
C3 C10 C11 C12 -175.5(4) . . . . ?
C10 N2 C14 C13 -0.2(6) . . . . ?
C10 N2 C14 C4 179.5(3) . . . . ?
V1 O1 C1 O2 -179.2(3) . . . . ?
V1 O1 C1 C5 0.7(4) . . . . ?
N1 C5 C1 O2 -178.1(4) . . . . ?
C6 C5 C1 O2 4.7(7) . . . . ?
N1 C5 C1 O1 2.0(5) . . . . ?
C6 C5 C1 O1 -175.2(4) . . . . ?
N2 C14 C13 C12 2.3(7) . . . . ?
C4 C14 C13 C12 -177.4(4) . . . . ?
C5 N1 C9 C8 -0.6(6) . . . . ?
V1 N1 C9 C8 -175.1(3) . . . . ?
C5 N1 C9 C2 177.5(4) . . . . ?
V1 N1 C9 C2 3.0(5) . . . . ?
N1 C5 C6 C7 1.0(7) . . . . ?
C1 C5 C6 C7 178.0(4) . . . . ?
N2 C14 C4 O7 -16.6(6) . . . . ?
C13 C14 C4 O7 163.1(5) . . . . ?
N2 C14 C4 O8 163.5(4) . . . . ?
C13 C14 C4 O8 -16.8(7) . . . . ?
C14 C13 C12 C11 -1.8(7) . . . . ?
C10 C11 C12 C13 -0.6(7) . . . . ?
V1 O3 C2 O4 177.5(4) . . . . ?
V1 O3 C2 C9 -0.7(5) . . . . ?
N1 C9 C2 O4 -179.7(4) . . . . ?
C8 C9 C2 O4 -1.8(7) . . . . ?
N1 C9 C2 O3 -1.5(5) . . . . ?
C8 C9 C2 O3 176.4(4) . . . . ?
C5 C6 C7 C8 0.4(7) . . . . ?
C6 C7 C8 C9 -1.8(8) . . . . ?
N1 C9 C8 C7 2.0(7) . . . . ?
C2 C9 C8 C7 -175.8(4) . . . . ?

_diffrn_measured_fraction_theta_max 0.968
_diffrn_reflns_theta_full        25.95
_diffrn_measured_fraction_theta_full 0.968
_refine_diff_density_max         0.690
_refine_diff_density_min         -0.705
_refine_diff_density_rms         0.098
####################################################################### 
# 
# 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_2
_database_code_depnum_ccdc_archive 'CCDC 1056937'
_audit_update_record             
;
2015-10-10 deposited with the CCDC.
2015-11-16 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C15 H11 F3 N O9 V'
_chemical_formula_weight         457.19

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'
F F 0.0171 0.0103 '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_H-M   P2(1)/c

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                   15.3219(17)
_cell_length_b                   17.734(2)
_cell_length_c                   6.6947(8)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.641(2)
_cell_angle_gamma                90.00
_cell_volume                     1818.9(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    4462
_cell_measurement_theta_min      1.76
_cell_measurement_theta_max      28.44

_exptl_crystal_description       block
_exptl_crystal_colour            deepred
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.09
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.670
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             920
_exptl_absorpt_coefficient_mu    0.626
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8248
_exptl_absorpt_correction_T_max  0.9458
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(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 AXS SMART APEX II CCD'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0
_diffrn_reflns_number            11358
_diffrn_reflns_av_R_equivalents  0.0252
_diffrn_reflns_av_sigmaI/netI    0.0336
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_theta_min         1.76
_diffrn_reflns_theta_max         28.44
_reflns_number_total             4462
_reflns_number_gt                3371
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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 > 2sigma(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)+(0.0497P)²+0.5737P] 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         4462
_refine_ls_number_parameters     312
_refine_ls_number_restraints     128
_refine_ls_R_factor_all          0.0567
_refine_ls_R_factor_gt           0.0387
_refine_ls_wR_factor_ref         0.1066
_refine_ls_wR_factor_gt          0.0975
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_restrained_S_all      1.057
_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 0.52473(2) 0.375261(18) 0.31350(5) 0.02893(11) Uani 1 1 d . A .
O1W O 0.48894(11) 0.34822(9) 0.0289(2) 0.0433(4) Uani 1 1 d D . .
H1A H 0.4489(13) 0.3705(12) -0.027(4) 0.065 Uiso 1 1 d D . .
H1B H 0.5039(16) 0.3086(9) -0.022(4) 0.065 Uiso 1 1 d D . .
O1 O 0.40232(9) 0.42636(9) 0.3469(2) 0.0411(4) Uani 1 1 d . A .
O2W O 0.56116(11) 0.40508(9) 0.5987(2) 0.0417(4) Uani 1 1 d D . .
H2A H 0.5948(15) 0.3794(12) 0.664(3) 0.063 Uiso 1 1 d D . .
H2B H 0.5356(15) 0.4388(11) 0.656(3) 0.063 Uiso 1 1 d D . .
O2 O 0.42078(10) 0.31048(9) 0.4302(3) 0.0495(4) Uani 1 1 d . A .
O4 O 0.63985(10) 0.57412(9) 0.1298(2) 0.0449(4) Uani 1 1 d . . .
O5 O 0.54622(9) 0.48536(8) 0.2309(2) 0.0343(3) Uani 1 1 d . . .
O6 O 0.68261(10) 0.18812(8) 0.2652(2) 0.0430(4) Uani 1 1 d . . .
O7 O 0.57592(9) 0.26915(8) 0.3409(2) 0.0353(3) Uani 1 1 d . . .
N1 N 0.65638(11) 0.38209(9) 0.2288(2) 0.0312(4) Uani 1 1 d . . .
C1 C 0.27689(15) 0.36117(15) 0.4682(3) 0.0458(6) Uani 1 1 d . A .
C2 C 0.22200(17) 0.42124(16) 0.4414(4) 0.0612(7) Uani 1 1 d D . .
H2C H 0.2436 0.4651 0.3839 0.073 Uiso 0.374(4) 1 calc PR A 1
O3 O 0.2496(2) 0.48772(17) 0.3711(6) 0.0833(14) Uani 0.626(4) 1 d PD A 2
H3A H 0.3019 0.4852 0.3472 0.125 Uiso 0.626(4) 1 calc PR A 2
C3 C 0.13566(19) 0.4188(2) 0.4971(5) 0.0819(10) Uani 1 1 d . A .
H3 H 0.0992 0.4601 0.4772 0.098 Uiso 1 1 calc R . .
C4 C 0.10511(19) 0.3542(3) 0.5819(5) 0.0827(11) Uani 1 1 d . . .
C5 C 0.1573(2) 0.2930(2) 0.6112(5) 0.0831(11) Uani 1 1 d . A .
H5 H 0.1357 0.2492 0.6690 0.100 Uiso 1 1 calc R . .
C6 C 0.24351(16) 0.29771(18) 0.5526(4) 0.0625(8) Uani 1 1 d D . .
H6 H 0.2798 0.2562 0.5716 0.075 Uiso 0.626(4) 1 calc PR A 2
O3B O 0.2913(3) 0.2355(2) 0.5847(9) 0.075(2) Uani 0.374(4) 1 d PD A 1
H3D H 0.3413 0.2427 0.5465 0.113 Uiso 0.374(4) 1 calc PR A 1
C7 C 0.36966(14) 0.36575(13) 0.4137(3) 0.0396(5) Uani 1 1 d . . .
C8 C 0.0114(3) 0.3527(3) 0.6519(7) 0.1268(19) Uani 1 1 d D A .
C9 C 0.68914(14) 0.44828(12) 0.1725(3) 0.0355(5) Uani 1 1 d . . .
C10 C 0.77514(15) 0.45523(15) 0.1172(4) 0.0496(6) Uani 1 1 d . . .
H10 H 0.7975 0.5014 0.0767 0.059 Uiso 1 1 calc R . .
C11 C 0.82727(16) 0.39148(16) 0.1237(4) 0.0561(7) Uani 1 1 d . . .
H11 H 0.8860 0.3949 0.0911 0.067 Uiso 1 1 calc R . .
C12 C 0.79252(15) 0.32286(14) 0.1784(4) 0.0463(6) Uani 1 1 d . . .
H12 H 0.8267 0.2795 0.1803 0.056 Uiso 1 1 calc R . .
C13 C 0.70598(13) 0.32035(12) 0.2302(3) 0.0342(4) Uani 1 1 d . . .
C14 C 0.62152(14) 0.50913(12) 0.1762(3) 0.0345(5) Uani 1 1 d . . .
C15 C 0.65359(14) 0.25215(12) 0.2826(3) 0.0331(4) Uani 1 1 d . . .
F1 F -0.0143(7) 0.4193(4) 0.730(3) 0.170(5) Uani 0.469(13) 1 d PDU A 1
F2 F -0.0075(7) 0.3025(8) 0.788(2) 0.174(5) Uani 0.469(13) 1 d PDU A 1
F3 F -0.0414(6) 0.3412(13) 0.4971(13) 0.189(5) Uani 0.469(13) 1 d PDU A 1
F1B F -0.0179(5) 0.2829(4) 0.653(3) 0.188(4) Uani 0.531(13) 1 d PDU A 2
F2B F 0.0096(6) 0.3768(12) 0.8364(15) 0.204(5) Uani 0.531(13) 1 d PDU A 2
F3B F -0.0406(5) 0.3938(8) 0.540(2) 0.170(4) Uani 0.531(13) 1 d PDU A 2


_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 O1W 2.0339(15) . ?
V1 O7 2.0461(14) . ?
V1 O2W 2.0527(15) . ?
V1 O5 2.0569(14) . ?
V1 O1 2.0973(15) . ?
V1 N1 2.1050(17) . ?
V1 O2 2.1201(16) . ?
V1 C7 2.482(2) . ?
O1W H1A 0.817(10) . ?
O1W H1B 0.814(10) . ?
O1 C7 1.269(3) . ?
O2W H2A 0.810(9) . ?
O2W H2B 0.811(9) . ?
O2 C7 1.259(3) . ?
O4 C14 1.227(2) . ?
O5 C14 1.285(2) . ?
O6 C15 1.225(2) . ?
O7 C15 1.292(2) . ?
N1 C9 1.333(3) . ?
N1 C13 1.333(3) . ?
C1 C6 1.362(4) . ?
C1 C2 1.368(4) . ?
C1 C7 1.474(3) . ?
C2 O3 1.33996(16) . ?
C2 C3 1.379(4) . ?
C2 H2C 0.9300 . ?
O3 H3A 0.8200 . ?
C3 C4 1.364(5) . ?
C3 H3 0.9300 . ?
C4 C5 1.362(5) . ?
C4 C8 1.516(5) . ?
C5 C6 1.384(4) . ?
C5 H5 0.9300 . ?
C6 O3B 1.33996(16) . ?
C6 H6 0.9300 . ?
O3B H3D 0.8200 . ?
C8 F2 1.307(6) . ?
C8 F3B 1.308(6) . ?
C8 F2B 1.308(6) . ?
C8 F1B 1.317(6) . ?
C8 F3 1.323(6) . ?
C8 F1 1.352(6) . ?
C9 C10 1.378(3) . ?
C9 C14 1.496(3) . ?
C10 C11 1.385(4) . ?
C10 H10 0.9300 . ?
C11 C12 1.379(3) . ?
C11 H11 0.9300 . ?
C12 C13 1.375(3) . ?
C12 H12 0.9300 . ?
C13 C15 1.495(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
O1W V1 O7 88.06(6) . . ?
O1W V1 O2W 178.69(7) . . ?
O7 V1 O2W 93.08(6) . . ?
O1W V1 O5 90.81(6) . . ?
O7 V1 O5 146.59(6) . . ?
O2W V1 O5 87.87(6) . . ?
O1W V1 O1 88.26(6) . . ?
O7 V1 O1 136.90(6) . . ?
O2W V1 O1 91.35(6) . . ?
O5 V1 O1 76.39(6) . . ?
O1W V1 N1 90.59(7) . . ?
O7 V1 N1 73.11(6) . . ?
O2W V1 N1 89.10(7) . . ?
O5 V1 N1 73.51(6) . . ?
O1 V1 N1 149.85(6) . . ?
O1W V1 O2 91.24(7) . . ?
O7 V1 O2 75.96(6) . . ?
O2W V1 O2 89.68(7) . . ?
O5 V1 O2 137.45(6) . . ?
O1 V1 O2 61.21(6) . . ?
N1 V1 O2 148.94(6) . . ?
O1W V1 C7 89.32(7) . . ?
O7 V1 C7 106.29(7) . . ?
O2W V1 C7 90.99(7) . . ?
O5 V1 C7 107.09(7) . . ?
O1 V1 C7 30.74(7) . . ?
N1 V1 C7 179.40(7) . . ?
O2 V1 C7 30.48(7) . . ?
V1 O1W H1A 120.5(17) . . ?
V1 O1W H1B 121.2(17) . . ?
H1A O1W H1B 116.2(17) . . ?
C7 O1 V1 91.62(13) . . ?
V1 O2W H2A 121.3(17) . . ?
V1 O2W H2B 119.9(17) . . ?
H2A O2W H2B 118.0(17) . . ?
C7 O2 V1 90.85(14) . . ?
C14 O5 V1 122.33(13) . . ?
C15 O7 V1 122.75(13) . . ?
C9 N1 C13 120.60(18) . . ?
C9 N1 V1 119.47(14) . . ?
C13 N1 V1 119.93(14) . . ?
C6 C1 C2 117.7(2) . . ?
C6 C1 C7 121.1(2) . . ?
C2 C1 C7 121.2(2) . . ?
O3 C2 C1 122.3(3) . . ?
O3 C2 C3 115.5(3) . . ?
C1 C2 C3 122.0(3) . . ?
O3 C2 H2C 4.9 . . ?
C1 C2 H2C 119.0 . . ?
C3 C2 H2C 119.0 . . ?
C2 O3 H3A 109.5 . . ?
C4 C3 C2 118.3(3) . . ?
C4 C3 H3 120.9 . . ?
C2 C3 H3 120.9 . . ?
C5 C4 C3 121.7(3) . . ?
C5 C4 C8 119.9(4) . . ?
C3 C4 C8 118.3(4) . . ?
C4 C5 C6 118.2(3) . . ?
C4 C5 H5 120.9 . . ?
C6 C5 H5 120.9 . . ?
O3B C6 C1 122.7(3) . . ?
O3B C6 C5 115.2(3) . . ?
C1 C6 C5 122.1(3) . . ?
O3B C6 H6 3.7 . . ?
C1 C6 H6 119.0 . . ?
C5 C6 H6 119.0 . . ?
C6 O3B H3D 109.5 . . ?
O2 C7 O1 116.3(2) . . ?
O2 C7 C1 122.4(2) . . ?
O1 C7 C1 121.3(2) . . ?
O2 C7 V1 58.67(11) . . ?
O1 C7 V1 57.65(11) . . ?
C1 C7 V1 178.47(18) . . ?
F2 C8 F3B 129.7(8) . . ?
F2 C8 F2B 63.8(5) . . ?
F3B C8 F2B 109.7(6) . . ?
F2 C8 F1B 43.8(5) . . ?
F3B C8 F1B 108.7(5) . . ?
F2B C8 F1B 107.0(5) . . ?
F2 C8 F3 107.5(6) . . ?
F3B C8 F3 43.6(6) . . ?
F2B C8 F3 140.4(7) . . ?
F1B C8 F3 69.7(6) . . ?
F2 C8 F1 105.0(5) . . ?
F3B C8 F1 63.6(5) . . ?
F2B C8 F1 48.7(5) . . ?
F1B C8 F1 135.9(6) . . ?
F3 C8 F1 105.0(6) . . ?
F2 C8 C4 116.4(5) . . ?
F3B C8 C4 112.8(6) . . ?
F2B C8 C4 108.5(5) . . ?
F1B C8 C4 110.0(5) . . ?
F3 C8 C4 109.5(6) . . ?
F1 C8 C4 112.6(5) . . ?
N1 C9 C10 121.3(2) . . ?
N1 C9 C14 111.55(18) . . ?
C10 C9 C14 127.2(2) . . ?
C9 C10 C11 118.1(2) . . ?
C9 C10 H10 120.9 . . ?
C11 C10 H10 120.9 . . ?
C12 C11 C10 120.3(2) . . ?
C12 C11 H11 119.9 . . ?
C10 C11 H11 119.9 . . ?
C13 C12 C11 118.1(2) . . ?
C13 C12 H12 120.9 . . ?
C11 C12 H12 120.9 . . ?
N1 C13 C12 121.5(2) . . ?
N1 C13 C15 111.01(17) . . ?
C12 C13 C15 127.4(2) . . ?
O4 C14 O5 126.1(2) . . ?
O4 C14 C9 120.8(2) . . ?
O5 C14 C9 113.09(18) . . ?
O6 C15 O7 125.5(2) . . ?
O6 C15 C13 122.07(19) . . ?
O7 C15 C13 112.38(17) . . ?

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
O1W H1A O4 0.817(10) 1.807(10) 2.622(2) 175(3) 3_665
O1W H1B O7 0.814(10) 1.997(12) 2.781(2) 161(3) 4_565
O2W H2A O6 0.810(9) 1.920(10) 2.719(2) 168(2) 4_566
O1W H1B O2 0.814(10) 2.48(2) 3.071(2) 130(2) 4_565
O2W H2B O5 0.811(9) 1.996(10) 2.797(2) 170(3) 3_666
O2W H2B O1 0.811(9) 2.57(2) 3.062(2) 120(2) 3_666
O3 H3A O1 0.82 1.86 2.587(3) 147.3 .
O3B H3D O2 0.82 1.89 2.611(5) 146.8 .

_diffrn_measured_fraction_theta_max 0.973
_diffrn_reflns_theta_full        28.44
_diffrn_measured_fraction_theta_full 0.973
_refine_diff_density_max         0.511
_refine_diff_density_min         -0.467
_refine_diff_density_rms         0.052

