# Electronic Supplementary Material (ESI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 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_I
_database_code_depnum_ccdc_archive 'CCDC 1058817'
_audit_update_record             
;
2015-04-10 deposited with the CCDC.
2015-09-14 downloaded from the CCDC.
;
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C16 H16 F N2 O5 V'
_chemical_formula_iupac          ?
_chemical_formula_weight         386.25

_chemical_melting_point          437-439

_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   7.9908(3)
_cell_length_b                   17.1771(6)
_cell_length_c                   11.9692(5)
_cell_angle_alpha                90
_cell_angle_beta                 100.2079(18)
_cell_angle_gamma                90
_cell_volume                     1616.87(11)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5914
_cell_measurement_theta_min      2.8486
_cell_measurement_theta_max      31.0669
_cell_measurement_temperature    103.(2)

_exptl_crystal_description       block
_exptl_crystal_colour            red
_exptl_crystal_size_max          0.360
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.120
_exptl_crystal_density_diffrn    1.587
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             792

_exptl_absorpt_coefficient_mu    0.655
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2012/1 (Bruker AXS Inc.)'
_exptl_absorpt_correction_T_min  0.82
_exptl_absorpt_correction_T_max  0.93

_exptl_special_details           
;
;

_diffrn_ambient_temperature      103.(2)

_diffrn_source                   'fine-focus sealed tube'
_diffrn_source_type              ?

_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  graphite

_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'

_diffrn_detector_area_resol_mean 8.3333

_diffrn_reflns_number            21857
_diffrn_reflns_av_R_equivalents  0.0370
_diffrn_reflns_av_unetI/netI     0.0322
_diffrn_reflns_theta_min         2.59
_diffrn_reflns_theta_max         31.09
_diffrn_reflns_theta_full        31.09
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       14

_refine_special_details          
;
;

_reflns_number_total             5189
_reflns_number_gt                4378
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0426
_refine_ls_R_factor_gt           0.0332
_refine_ls_wR_factor_gt          0.0816
_refine_ls_wR_factor_ref         0.0872
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_restrained_S_all      1.039
_refine_ls_number_reflns         5189
_refine_ls_number_parameters     232
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0387P)²+0.7994P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.476
_refine_diff_density_min         -0.374
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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'

_computing_data_collection       'APEX2 (Bruker AXS Inc., 2013)'
_computing_cell_refinement       'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'XP (Bruker AXS Inc., 2013)'
_computing_publication_material  'APEX2 (Bruker AXS Inc., 2013)'

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
V V1 0.29301(3) 0.48136(2) 0.24810(2) 0.01207(6) Uani d . . . 1 . .
C C1 0.11554(16) 0.38112(7) 0.08001(10) 0.0114(2) Uani d . . . 1 . .
C C2 0.02016(16) 0.30961(7) 0.04105(11) 0.0116(2) Uani d . . . 1 . .
C C3 -0.01014(18) 0.25580(8) 0.12268(11) 0.0166(3) Uani d . . . 1 . .
H H3 0.0331 0.2656 0.2006 0.02 Uiso calc U . R 1 . .
C C4 -0.1021(2) 0.18839(8) 0.09199(12) 0.0195(3) Uani d . . . 1 . .
H H4 -0.1228 0.1518 0.1475 0.023 Uiso calc U . R 1 . .
C C5 -0.16268(18) 0.17613(8) -0.02180(12) 0.0163(3) Uani d . . . 1 . .
C C6 -0.13358(18) 0.22720(8) -0.10508(11) 0.0165(3) Uani d . . . 1 . .
H H6 -0.1763 0.2166 -0.1828 0.02 Uiso calc U . R 1 . .
C C7 -0.04097(18) 0.29429(8) -0.07341(11) 0.0152(2) Uani d . . . 1 . .
H H7 -0.019 0.3299 -0.1297 0.018 Uiso calc U . R 1 . .
C C8 0.30797(17) 0.54480(7) 0.00919(11) 0.0124(2) Uani d . . . 1 . .
H H8 0.2857 0.5404 -0.0712 0.015 Uiso calc U . R 1 . .
C C9 0.40923(17) 0.60950(7) 0.05931(11) 0.0126(2) Uani d . . . 1 . .
C C10 0.42714(17) 0.62719(7) 0.17598(11) 0.0137(2) Uani d . . . 1 . .
C C11 0.52345(19) 0.69198(8) 0.21951(12) 0.0179(3) Uani d . . . 1 . .
H H11 0.5369 0.7038 0.2981 0.022 Uiso calc U . R 1 . .
C C12 0.59922(19) 0.73885(8) 0.14869(12) 0.0189(3) Uani d . . . 1 . .
H H12 0.6648 0.7825 0.1791 0.023 Uiso calc U . R 1 . .
C C13 0.57995(18) 0.72240(8) 0.03310(12) 0.0180(3) Uani d . . . 1 . .
H H13 0.6314 0.755 -0.0152 0.022 Uiso calc U . R 1 . .
C C14 0.48592(18) 0.65863(8) -0.01092(12) 0.0152(2) Uani d . . . 1 . .
H H14 0.4728 0.6477 -0.0898 0.018 Uiso calc U . R 1 . .
C C15 0.3299(2) 0.43053(8) 0.48442(12) 0.0193(3) Uani d . . . 1 . .
H H15A 0.2562 0.3887 0.5033 0.029 Uiso calc U . R 1 . .
H H15B 0.3535 0.4672 0.5479 0.029 Uiso calc U . R 1 . .
H H15C 0.437 0.4083 0.4701 0.029 Uiso calc U . R 1 . .
C C16 -0.1087(2) 0.50962(11) 0.28031(13) 0.0252(3) Uani d . . . 1 . .
H H16A -0.1332 0.4541 0.2676 0.038 Uiso calc U . R 1 . .
H H16B -0.2129 0.5398 0.2559 0.038 Uiso calc U . R 1 . .
H H16C -0.0668 0.5188 0.3613 0.038 Uiso calc U . R 1 . .
F F1 -0.25434(12) 0.11129(5) -0.05325(8) 0.0246(2) Uani d . . . 1 . .
N N1 0.24585(14) 0.49242(6) 0.06794(9) 0.0111(2) Uani d . . . 1 . .
N N2 0.14783(14) 0.43386(6) 0.00730(9) 0.0115(2) Uani d . . . 1 . .
O O1 0.47743(13) 0.44468(6) 0.25660(8) 0.0187(2) Uani d . . . 1 . .
O O2 0.16460(13) 0.38854(5) 0.18922(8) 0.01443(19) Uani d . . . 1 . .
O O3 0.34672(13) 0.58632(6) 0.24502(8) 0.0167(2) Uani d . . . 1 . .
O O4 0.01724(13) 0.53318(6) 0.21661(8) 0.01466(19) Uani d . . . 1 . .
H H1O -0.025(3) 0.5420(12) 0.1499(19) 0.032(6) Uiso d . . . 1 . .
O O5 0.24758(13) 0.47009(6) 0.38605(8) 0.01517(19) Uani d . . . 1 . .


_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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
V1 O1 . 1.5893(11) ?
V1 O5 . 1.7630(10) ?
V1 O3 . 1.8552(10) ?
V1 O2 . 1.9584(9) ?
V1 N1 . 2.1307(11) ?
V1 O4 . 2.3443(10) ?
C1 O2 . 1.3027(15) ?
C1 N2 . 1.3131(16) ?
C1 C2 . 1.4768(17) ?
C2 C7 . 1.3956(18) ?
C2 C3 . 1.3969(18) ?
C3 C4 . 1.3859(19) ?
C3 H3 . 0.95 ?
C4 C5 . 1.3783(19) ?
C4 H4 . 0.95 ?
C5 F1 . 1.3495(15) ?
C5 C6 . 1.3782(19) ?
C6 C7 . 1.3856(18) ?
C6 H6 . 0.95 ?
C7 H7 . 0.95 ?
C8 N1 . 1.2939(16) ?
C8 C9 . 1.4413(17) ?
C8 H8 . 0.95 ?
C9 C14 . 1.4061(18) ?
C9 C10 . 1.4114(18) ?
C10 O3 . 1.3330(16) ?
C10 C11 . 1.4001(18) ?
C11 C12 . 1.384(2) ?
C11 H11 . 0.95 ?
C12 C13 . 1.394(2) ?
C12 H12 . 0.95 ?
C13 C14 . 1.3791(19) ?
C13 H13 . 0.95 ?
C14 H14 . 0.95 ?
C15 O5 . 1.4164(16) ?
C15 H15A . 0.98 ?
C15 H15B . 0.98 ?
C15 H15C . 0.98 ?
C16 O4 . 1.4250(17) ?
C16 H16A . 0.98 ?
C16 H16B . 0.98 ?
C16 H16C . 0.98 ?
N1 N2 . 1.3967(14) ?
O4 H1O . 0.82(2) ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
O1 V1 O5 . . 103.83(5) ?
O1 V1 O3 . . 99.87(5) ?
O5 V1 O3 . . 102.24(4) ?
O1 V1 O2 . . 96.95(5) ?
O5 V1 O2 . . 93.78(4) ?
O3 V1 O2 . . 153.17(4) ?
O1 V1 N1 . . 95.50(5) ?
O5 V1 N1 . . 158.25(5) ?
O3 V1 N1 . . 83.88(4) ?
O2 V1 N1 . . 73.80(4) ?
O1 V1 O4 . . 174.45(4) ?
O5 V1 O4 . . 81.29(4) ?
O3 V1 O4 . . 80.91(4) ?
O2 V1 O4 . . 80.42(4) ?
N1 V1 O4 . . 79.10(4) ?
O2 C1 N2 . . 122.55(11) ?
O2 C1 C2 . . 116.42(11) ?
N2 C1 C2 . . 121.04(11) ?
C7 C2 C3 . . 119.20(12) ?
C7 C2 C1 . . 122.55(11) ?
C3 C2 C1 . . 118.24(11) ?
C4 C3 C2 . . 121.13(12) ?
C4 C3 H3 . . 119.4 ?
C2 C3 H3 . . 119.4 ?
C5 C4 C3 . . 117.80(12) ?
C5 C4 H4 . . 121.1 ?
C3 C4 H4 . . 121.1 ?
F1 C5 C6 . . 118.45(12) ?
F1 C5 C4 . . 118.68(12) ?
C6 C5 C4 . . 122.87(12) ?
C5 C6 C7 . . 118.81(12) ?
C5 C6 H6 . . 120.6 ?
C7 C6 H6 . . 120.6 ?
C6 C7 C2 . . 120.16(12) ?
C6 C7 H7 . . 119.9 ?
C2 C7 H7 . . 119.9 ?
N1 C8 C9 . . 123.44(12) ?
N1 C8 H8 . . 118.3 ?
C9 C8 H8 . . 118.3 ?
C14 C9 C10 . . 118.93(12) ?
C14 C9 C8 . . 119.07(11) ?
C10 C9 C8 . . 121.93(12) ?
O3 C10 C11 . . 118.78(12) ?
O3 C10 C9 . . 121.64(11) ?
C11 C10 C9 . . 119.48(12) ?
C12 C11 C10 . . 120.38(13) ?
C12 C11 H11 . . 119.8 ?
C10 C11 H11 . . 119.8 ?
C11 C12 C13 . . 120.45(13) ?
C11 C12 H12 . . 119.8 ?
C13 C12 H12 . . 119.8 ?
C14 C13 C12 . . 119.82(13) ?
C14 C13 H13 . . 120.1 ?
C12 C13 H13 . . 120.1 ?
C13 C14 C9 . . 120.93(13) ?
C13 C14 H14 . . 119.5 ?
C9 C14 H14 . . 119.5 ?
O5 C15 H15A . . 109.5 ?
O5 C15 H15B . . 109.5 ?
H15A C15 H15B . . 109.5 ?
O5 C15 H15C . . 109.5 ?
H15A C15 H15C . . 109.5 ?
H15B C15 H15C . . 109.5 ?
O4 C16 H16A . . 109.5 ?
O4 C16 H16B . . 109.5 ?
H16A C16 H16B . . 109.5 ?
O4 C16 H16C . . 109.5 ?
H16A C16 H16C . . 109.5 ?
H16B C16 H16C . . 109.5 ?
C8 N1 N2 . . 116.89(11) ?
C8 N1 V1 . . 126.58(9) ?
N2 N1 V1 . . 116.36(8) ?
C1 N2 N1 . . 108.09(10) ?
C1 O2 V1 . . 119.08(8) ?
C10 O3 V1 . . 131.51(8) ?
C16 O4 V1 . . 122.63(9) ?
C16 O4 H1O . . 111.4(15) ?
V1 O4 H1O . . 115.9(15) ?
C15 O5 V1 . . 133.54(9) ?


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: methanol'
_chemical_properties_physical    'Light-sensitive, Photo-sensitive'
_exptl_crystal_preparation       Luminescent
####################################################################### 
# 
# 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_I
_database_code_depnum_ccdc_archive 'CCDC 1058818'
_audit_update_record             
;
2015-04-10 deposited with the CCDC.
2015-09-14 downloaded from the CCDC.
;
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C30 H44 N2 O8 V2'
_chemical_formula_iupac          ?
_chemical_formula_weight         662.55

_chemical_melting_point          ?

_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   12.1706(6)
_cell_length_b                   11.0345(5)
_cell_length_c                   23.8844(12)
_cell_angle_alpha                90
_cell_angle_beta                 100.8835(17)
_cell_angle_gamma                90
_cell_volume                     3149.9(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4220
_cell_measurement_theta_min      2.5122
_cell_measurement_theta_max      30.4199
_cell_measurement_temperature    133.(2)

_exptl_crystal_description       plate
_exptl_crystal_colour            red
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.160
_exptl_crystal_size_min          0.060
_exptl_crystal_density_diffrn    1.397
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1392

_exptl_absorpt_coefficient_mu    0.644
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2014/3 (Bruker AXS Inc.)'
_exptl_absorpt_correction_T_min  0.87
_exptl_absorpt_correction_T_max  0.96

_exptl_special_details           
;
;

_diffrn_ambient_temperature      133.(2)

_diffrn_source                   'fine-focus sealed tube'
_diffrn_source_type              ?

_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean 8.3333
_diffrn_reflns_number            18722
_diffrn_reflns_av_R_equivalents  0.0440
_diffrn_reflns_av_unetI/netI     0.0479
_diffrn_reflns_theta_min         2.55
_diffrn_reflns_theta_max         31.04
_diffrn_reflns_theta_full        31.04
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       34

_refine_special_details          
;
;

_reflns_number_total             5001
_reflns_number_gt                3899
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0602
_refine_ls_R_factor_gt           0.0409
_refine_ls_wR_factor_gt          0.0942
_refine_ls_wR_factor_ref         0.1048
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_restrained_S_all      1.045
_refine_ls_number_reflns         5001
_refine_ls_number_parameters     222
_refine_ls_number_restraints     83
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0418P)²+2.8598P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.432
_refine_diff_density_min         -0.434
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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'

_computing_data_collection       'APEX2 (Bruker AXS Inc., 2014)'
_computing_cell_refinement       'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    'XP (Bruker AXS Inc., 2014)'
_computing_publication_material  'APEX2 (Bruker AXS Inc., 2014)'

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
V V1 0.13740(2) 0.98492(2) 0.02923(2) 0.01615(8) Uani d . . . 1.0 . .
C C1 0.12344(13) 0.79535(13) 0.11642(7) 0.0160(3) Uani d . . . 1.0 . .
C C2 0.13581(14) 0.77544(14) 0.17617(7) 0.0174(3) Uani d . . . 1.0 . .
C C3 0.20419(15) 0.86260(14) 0.21965(7) 0.0193(3) Uani d . . . 1.0 . .
C C4 0.32630(16) 0.86241(18) 0.21177(8) 0.0278(4) Uani d . . . 1.0 . .
H H4A 0.3698 0.919 0.2389 0.042 Uiso calc U . R 1.0 . .
H H4B 0.3298 0.8874 0.1728 0.042 Uiso calc U . R 1.0 . .
H H4C 0.3574 0.7806 0.2186 0.042 Uiso calc U . R 1.0 . .
C C5 0.15698(17) 0.99264(15) 0.21245(8) 0.0263(4) Uani d . . . 1.0 . .
H H5A 0.2014 1.0457 0.241 0.039 Uiso calc U . R 1.0 . .
H H5B 0.079 0.9925 0.2176 0.039 Uiso calc U . R 1.0 . .
H H5C 0.1606 1.0223 0.1742 0.039 Uiso calc U . R 1.0 . .
C C6 0.20294(18) 0.82519(17) 0.28130(8) 0.0294(4) Uani d . . . 1.0 . .
H H6A 0.2377 0.7452 0.2887 0.044 Uiso calc U . R 1.0 . .
H H6B 0.1255 0.8218 0.2872 0.044 Uiso calc U . R 1.0 . .
H H6C 0.2449 0.8847 0.3074 0.044 Uiso calc U . R 1.0 . .
C C7 0.08627(16) 0.67190(15) 0.19359(8) 0.0242(4) Uani d . . . 1.0 . .
H H7 0.0927 0.6573 0.2333 0.029 Uiso calc U . R 1.0 . .
C C8 0.02752(17) 0.58863(17) 0.15516(9) 0.0300(4) Uani d . . . 1.0 . .
H H8 -0.0065 0.5199 0.1687 0.036 Uiso calc U . R 1.0 . .
C C9 0.01916(16) 0.60665(16) 0.09771(8) 0.0253(4) Uani d . . . 1.0 . .
H H9 -0.0191 0.5491 0.0715 0.03 Uiso calc U . R 1.0 . .
C C10 0.06670(14) 0.70943(14) 0.07759(7) 0.0183(3) Uani d . . . 1.0 . .
C C11 0.06946(15) 0.71693(14) 0.01713(7) 0.0203(3) Uani d . . . 1.0 . .
H H11 0.0424 0.6488 -0.0057 0.024 Uiso calc U . R 1.0 . .
C C12 0.1294(6) 0.7867(7) -0.0664(3) 0.0223(12) Uani d U P D 0.631(5) A 1
H H12A 0.1068 0.7031 -0.0785 0.027 Uiso calc U P R 0.631(5) A 1
H H12B 0.2111 0.7933 -0.0644 0.027 Uiso calc U P R 0.631(5) A 1
C C13 0.0705(3) 0.8749(3) -0.11144(12) 0.0241(7) Uani d U P D 0.631(5) A 1
H H13A 0.1004 0.8638 -0.1469 0.029 Uiso calc U P R 0.631(5) A 1
H H13B -0.0103 0.8555 -0.1201 0.029 Uiso calc U P R 0.631(5) A 1
C C14 -0.0852(12) 0.9943(12) 0.0930(4) 0.0228(19) Uani d U P D 0.631(5) A 1
H H14A -0.0431 0.9421 0.1234 0.027 Uiso calc U P R 0.631(5) A 1
H H14B -0.1653 0.9725 0.0881 0.027 Uiso calc U P R 0.631(5) A 1
C C12A 0.1061(12) 0.7899(13) -0.0696(5) 0.025(2) Uani d U P D 0.369(5) A 2
H H12C 0.0291 0.7728 -0.09 0.03 Uiso calc U P R 0.369(5) A 2
H H12D 0.1532 0.7189 -0.0744 0.03 Uiso calc U P R 0.369(5) A 2
C C13A 0.1505(5) 0.9002(4) -0.0960(2) 0.0248(12) Uani d U P D 0.369(5) A 2
H H13C 0.1549 0.8815 -0.136 0.03 Uiso calc U P R 0.369(5) A 2
H H13D 0.2274 0.9173 -0.0753 0.03 Uiso calc U P R 0.369(5) A 2
C C14A -0.0791(18) 0.986(2) 0.0948(6) 0.018(3) Uani d U P D 0.369(5) A 2
H H14C -0.0112 0.9925 0.1249 0.022 Uiso calc U P R 0.369(5) A 2
H H14D -0.1219 0.9144 0.1031 0.022 Uiso calc U P R 0.369(5) A 2
C C15 0.2182(2) 1.2206(2) 0.07130(10) 0.0484(6) Uani d . . . 1.0 . .
H H15A 0.2796 1.1972 0.0523 0.073 Uiso calc U . R 1.0 . .
H H15B 0.2474 1.2347 0.1119 0.073 Uiso calc U . R 1.0 . .
H H15C 0.1833 1.2951 0.0539 0.073 Uiso calc U . R 1.0 . .
N N1 0.10507(12) 0.80688(12) -0.00823(6) 0.0186(3) Uani d . . D 1.0 . .
O O1 0.25800(11) 0.99207(11) 0.01211(6) 0.0245(3) Uani d . . . 1.0 . .
O O2 0.16815(10) 0.89304(10) 0.09743(5) 0.0173(2) Uani d . . . 1.0 . .
O O3 -0.04698(10) 0.97128(10) 0.04054(5) 0.0173(2) Uani d . . D 1.0 . .
O O4 0.13822(11) 1.12748(10) 0.06525(5) 0.0231(3) Uani d . . . 1.0 . .


_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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
V1 O1 . 1.5984(13) ?
V1 O4 . 1.7920(12) ?
V1 O3 5_575 1.8787(12) ?
V1 O2 . 1.8950(11) ?
V1 N1 . 2.1639(14) ?
V1 O3 . 2.3152(12) ?
C1 O2 . 1.3254(18) ?
C1 C10 . 1.412(2) ?
C1 C2 . 1.424(2) ?
C2 C7 . 1.392(2) ?
C2 C3 . 1.539(2) ?
C3 C6 . 1.532(2) ?
C3 C4 . 1.533(3) ?
C3 C5 . 1.543(2) ?
C4 H4A . 0.98 ?
C4 H4B . 0.98 ?
C4 H4C . 0.98 ?
C5 H5A . 0.98 ?
C5 H5B . 0.98 ?
C5 H5C . 0.98 ?
C6 H6A . 0.98 ?
C6 H6B . 0.98 ?
C6 H6C . 0.98 ?
C7 C8 . 1.397(3) ?
C7 H7 . 0.95 ?
C8 C9 . 1.371(3) ?
C8 H8 . 0.95 ?
C9 C10 . 1.399(2) ?
C9 H9 . 0.95 ?
C10 C11 . 1.453(2) ?
C11 N1 . 1.280(2) ?
C11 H11 . 0.95 ?
C12 N1 . 1.490(7) ?
C12 C13 . 1.526(7) ?
C12 H12A . 0.99 ?
C12 H12B . 0.99 ?
C13 C14 5_575 1.510(13) ?
C13 H13A . 0.99 ?
C13 H13B . 0.99 ?
C14 O3 . 1.439(7) ?
C14 C13 5_575 1.510(13) ?
C14 H14A . 0.99 ?
C14 H14B . 0.99 ?
C12A N1 . 1.480(11) ?
C12A C13A . 1.516(13) ?
C12A H12C . 0.99 ?
C12A H12D . 0.99 ?
C13A C14A 5_575 1.53(2) ?
C13A H13C . 0.99 ?
C13A H13D . 0.99 ?
C14A O3 . 1.434(12) ?
C14A C13A 5_575 1.53(2) ?
C14A H14C . 0.99 ?
C14A H14D . 0.99 ?
C15 O4 . 1.404(2) ?
C15 H15A . 0.98 ?
C15 H15B . 0.98 ?
C15 H15C . 0.98 ?
O3 V1 5_575 1.8787(12) ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
O1 V1 O4 . . 99.06(6) ?
O1 V1 O3 . 5_575 99.95(6) ?
O4 V1 O3 . 5_575 98.58(5) ?
O1 V1 O2 . . 101.80(6) ?
O4 V1 O2 . . 94.29(5) ?
O3 V1 O2 5_575 . 152.58(5) ?
O1 V1 N1 . . 92.47(6) ?
O4 V1 N1 . . 168.40(6) ?
O3 V1 N1 5_575 . 80.59(5) ?
O2 V1 N1 . . 81.99(5) ?
O1 V1 O3 . . 171.98(6) ?
O4 V1 O3 . . 85.34(5) ?
O3 V1 O3 5_575 . 72.65(5) ?
O2 V1 O3 . . 84.45(5) ?
N1 V1 O3 . . 83.37(5) ?
O2 C1 C10 . . 120.18(15) ?
O2 C1 C2 . . 119.73(14) ?
C10 C1 C2 . . 120.06(14) ?
C7 C2 C1 . . 117.17(15) ?
C7 C2 C3 . . 121.39(15) ?
C1 C2 C3 . . 121.41(14) ?
C6 C3 C4 . . 107.67(15) ?
C6 C3 C2 . . 112.19(14) ?
C4 C3 C2 . . 109.24(13) ?
C6 C3 C5 . . 106.66(14) ?
C4 C3 C5 . . 109.68(15) ?
C2 C3 C5 . . 111.30(14) ?
C3 C4 H4A . . 109.5 ?
C3 C4 H4B . . 109.5 ?
H4A C4 H4B . . 109.5 ?
C3 C4 H4C . . 109.5 ?
H4A C4 H4C . . 109.5 ?
H4B C4 H4C . . 109.5 ?
C3 C5 H5A . . 109.5 ?
C3 C5 H5B . . 109.5 ?
H5A C5 H5B . . 109.5 ?
C3 C5 H5C . . 109.5 ?
H5A C5 H5C . . 109.5 ?
H5B C5 H5C . . 109.5 ?
C3 C6 H6A . . 109.5 ?
C3 C6 H6B . . 109.5 ?
H6A C6 H6B . . 109.5 ?
C3 C6 H6C . . 109.5 ?
H6A C6 H6C . . 109.5 ?
H6B C6 H6C . . 109.5 ?
C2 C7 C8 . . 122.72(17) ?
C2 C7 H7 . . 118.6 ?
C8 C7 H7 . . 118.6 ?
C9 C8 C7 . . 119.63(17) ?
C9 C8 H8 . . 120.2 ?
C7 C8 H8 . . 120.2 ?
C8 C9 C10 . . 120.27(17) ?
C8 C9 H9 . . 119.9 ?
C10 C9 H9 . . 119.9 ?
C9 C10 C1 . . 120.09(16) ?
C9 C10 C11 . . 118.44(15) ?
C1 C10 C11 . . 120.95(15) ?
N1 C11 C10 . . 125.99(15) ?
N1 C11 H11 . . 117.0 ?
C10 C11 H11 . . 117.0 ?
N1 C12 C13 . . 114.4(5) ?
N1 C12 H12A . . 108.7 ?
C13 C12 H12A . . 108.7 ?
N1 C12 H12B . . 108.7 ?
C13 C12 H12B . . 108.7 ?
H12A C12 H12B . . 107.6 ?
C14 C13 C12 5_575 . 113.0(6) ?
C14 C13 H13A 5_575 . 109.0 ?
C12 C13 H13A . . 109.0 ?
C14 C13 H13B 5_575 . 109.0 ?
C12 C13 H13B . . 109.0 ?
H13A C13 H13B . . 107.8 ?
O3 C14 C13 . 5_575 112.5(8) ?
O3 C14 H14A . . 109.1 ?
C13 C14 H14A 5_575 . 109.1 ?
O3 C14 H14B . . 109.1 ?
C13 C14 H14B 5_575 . 109.1 ?
H14A C14 H14B . . 107.8 ?
N1 C12A C13A . . 112.4(9) ?
N1 C12A H12C . . 109.1 ?
C13A C12A H12C . . 109.1 ?
N1 C12A H12D . . 109.1 ?
C13A C12A H12D . . 109.1 ?
H12C C12A H12D . . 107.9 ?
C12A C13A C14A . 5_575 113.7(10) ?
C12A C13A H13C . . 108.8 ?
C14A C13A H13C 5_575 . 108.8 ?
C12A C13A H13D . . 108.8 ?
C14A C13A H13D 5_575 . 108.8 ?
H13C C13A H13D . . 107.7 ?
O3 C14A C13A . 5_575 111.4(13) ?
O3 C14A H14C . . 109.4 ?
C13A C14A H14C 5_575 . 109.4 ?
O3 C14A H14D . . 109.4 ?
C13A C14A H14D 5_575 . 109.4 ?
H14C C14A H14D . . 108.0 ?
O4 C15 H15A . . 109.5 ?
O4 C15 H15B . . 109.5 ?
H15A C15 H15B . . 109.5 ?
O4 C15 H15C . . 109.5 ?
H15A C15 H15C . . 109.5 ?
H15B C15 H15C . . 109.5 ?
C11 N1 C12A . . 116.0(5) ?
C11 N1 C12 . . 118.0(3) ?
C11 N1 V1 . . 124.03(11) ?
C12A N1 V1 . . 119.3(5) ?
C12 N1 V1 . . 117.9(3) ?
C1 O2 V1 . . 134.59(10) ?
C14A O3 V1 . 5_575 124.0(9) ?
C14 O3 V1 . 5_575 119.7(6) ?
C14A O3 V1 . . 122.3(9) ?
C14 O3 V1 . . 124.7(6) ?
V1 O3 V1 5_575 . 107.34(5) ?
C15 O4 V1 . . 129.28(14) ?


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: methanol'
_chemical_properties_physical    'Light-sensitive, Photo-sensitive'
####################################################################### 
# 
# 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_I
_database_code_depnum_ccdc_archive 'CCDC 1058819'
_audit_update_record             
;
2015-04-10 deposited with the CCDC.
2015-09-14 downloaded from the CCDC.
;
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C15 H22 N O4 V'
_chemical_formula_iupac          ?
_chemical_formula_weight         331.27
_chemical_absolute_configuration ?

_chemical_melting_point          ?

_space_group_crystal_system      orthorhombic
_space_group_name_H-M_alt        'P n a 21'
_space_group_name_Hall           'P 2c -2n'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'x+1/2, -y+1/2, z'
'-x+1/2, y+1/2, z+1/2'

_cell_length_a                   14.7897(4)
_cell_length_b                   13.1867(3)
_cell_length_c                   7.8841(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1537.62(7)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5799
_cell_measurement_theta_min      2.7544
_cell_measurement_theta_max      31.0564
_cell_measurement_temperature    103.(2)

_exptl_crystal_description       block
_exptl_crystal_colour            red
_exptl_crystal_size_max          0.420
_exptl_crystal_size_mid          0.220
_exptl_crystal_size_min          0.200
_exptl_crystal_density_diffrn    1.431
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             696

_exptl_absorpt_coefficient_mu    0.660
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2014/3 (Bruker AXS Inc.)'
_exptl_absorpt_correction_T_min  0.72
_exptl_absorpt_correction_T_max  0.88

_exptl_special_details           
;
;

_diffrn_ambient_temperature      103.(2)

_diffrn_source                   'fine-focus sealed tube'
_diffrn_source_type              ?

_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean 8.3333
_diffrn_reflns_number            12950
_diffrn_reflns_av_R_equivalents  0.0265
_diffrn_reflns_av_unetI/netI     0.0377
_diffrn_reflns_theta_min         2.75
_diffrn_reflns_theta_max         31.07
_diffrn_reflns_theta_full        31.07
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11

_refine_special_details          
;
;

_reflns_number_total             4783
_reflns_number_gt                4492
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0317
_refine_ls_R_factor_gt           0.0289
_refine_ls_wR_factor_gt          0.0725
_refine_ls_wR_factor_ref         0.0740
_refine_ls_goodness_of_fit_ref   1.072
_refine_ls_restrained_S_all      1.072
_refine_ls_number_reflns         4783
_refine_ls_number_parameters     194
_refine_ls_number_restraints     1
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0407P)²] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.397
_refine_diff_density_min         -0.268
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 
;
Flack x determined using 1900 quotients [(I+)-(I-)]/[(I+)+(I-)]
(Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.037(9)

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'

_computing_data_collection       'APEX2 (Bruker AXS Inc., 2014)'
_computing_cell_refinement       'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    'XP (Bruker AXS Inc., 2014)'
_computing_publication_material  'APEX2 (Bruker AXS Inc., 2014)'

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
V V1 0.93022(2) 0.87770(2) 0.92650(6) 0.01050(8) Uani d . . . 1 . .
C C1 0.80690(12) 1.05997(13) 0.9019(2) 0.0111(3) Uani d . . . 1 . .
C C2 0.71513(13) 1.08592(14) 0.8709(3) 0.0123(3) Uani d . . . 1 . .
C C3 0.64153(13) 1.00364(15) 0.8625(3) 0.0137(4) Uani d . . . 1 . .
C C4 0.65759(15) 0.93649(16) 0.7059(3) 0.0185(4) Uani d . . . 1 . .
H H4A 0.6537 0.978 0.6031 0.028 Uiso calc U . R 1 . .
H H4B 0.6116 0.8831 0.7017 0.028 Uiso calc U . R 1 . .
H H4C 0.7177 0.9056 0.713 0.028 Uiso calc U . R 1 . .
C C5 0.64119(14) 0.93725(16) 1.0224(3) 0.0167(4) Uani d . . . 1 . .
H H5A 0.5899 0.8902 1.0178 0.025 Uiso calc U . R 1 . .
H H5B 0.6357 0.9805 1.123 0.025 Uiso calc U . R 1 . .
H H5C 0.6977 0.8987 1.0284 0.025 Uiso calc U . R 1 . .
C C6 0.54702(14) 1.05233(17) 0.8471(3) 0.0221(5) Uani d . . . 1 . .
H H6A 0.5369 1.098 0.9433 0.033 Uiso calc U . R 1 . .
H H6B 0.5008 0.9991 0.8473 0.033 Uiso calc U . R 1 . .
H H6C 0.5433 1.0908 0.741 0.033 Uiso calc U . R 1 . .
C C7 0.69690(14) 1.18813(15) 0.8424(3) 0.0169(4) Uani d . . . 1 . .
H H7 0.6363 1.2076 0.8189 0.02 Uiso calc U . R 1 . .
C C8 0.76330(15) 1.26329(15) 0.8464(3) 0.0181(4) Uani d . . . 1 . .
H H8 0.7476 1.3321 0.8264 0.022 Uiso calc U . R 1 . .
C C9 0.85170(14) 1.23727(15) 0.8796(3) 0.0160(4) Uani d . . . 1 . .
H H9 0.8971 1.2881 0.8841 0.019 Uiso calc U . R 1 . .
C C10 0.87433(13) 1.13523(13) 0.9066(3) 0.0123(4) Uani d . . . 1 . .
C C11 0.96725(13) 1.10935(14) 0.9438(3) 0.0129(4) Uani d . . . 1 . .
H H11 1.0082 1.1641 0.9591 0.015 Uiso calc U . R 1 . .
C C12 1.09603(13) 1.01278(16) 1.0076(3) 0.0154(4) Uani d . . . 1 . .
H H12A 1.1008 0.9783 1.1188 0.018 Uiso calc U . R 1 . .
H H12B 1.1208 1.0821 1.0203 0.018 Uiso calc U . R 1 . .
C C13 1.15192(13) 0.95496(16) 0.8772(3) 0.0162(4) Uani d . . . 1 . .
H H13A 1.1461 0.9884 0.7653 0.019 Uiso calc U . R 1 . .
H H13B 1.2164 0.957 0.9104 0.019 Uiso calc U . R 1 . .
C C14 1.12177(13) 0.84534(15) 0.8623(3) 0.0172(4) Uani d . . . 1 . .
H H14A 1.1602 0.8096 0.7787 0.021 Uiso calc U . R 1 . .
H H14B 1.1286 0.811 0.9732 0.021 Uiso calc U . R 1 . .
C C15 0.88114(16) 0.68208(16) 0.8099(3) 0.0236(5) Uani d . . . 1 . .
H H15A 0.8803 0.6538 0.9248 0.035 Uiso calc U . R 1 . .
H H15B 0.9413 0.6728 0.7602 0.035 Uiso calc U . R 1 . .
H H15C 0.8361 0.6471 0.7398 0.035 Uiso calc U . R 1 . .
N N1 0.99989(11) 1.01934(12) 0.95814(19) 0.0121(3) Uani d . . . 1 . .
O O1 0.94923(11) 0.83484(12) 1.11276(19) 0.0181(3) Uani d . . . 1 . .
O O2 0.82984(8) 0.96364(9) 0.9268(2) 0.0137(2) Uani d . . . 1 . .
O O3 1.02939(9) 0.84116(11) 0.80954(19) 0.0150(3) Uani d . . . 1 . .
O O4 0.86052(9) 0.78613(11) 0.8167(2) 0.0164(3) Uani d . . . 1 . .


_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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
V1 O1 . 1.5984(15) ?
V1 O3 . 1.7983(15) ?
V1 O4 . 1.8085(15) ?
V1 O2 . 1.8676(13) ?
V1 N1 . 2.1476(16) ?
C1 O2 . 1.329(2) ?
C1 C10 . 1.408(3) ?
C1 C2 . 1.421(3) ?
C2 C7 . 1.393(3) ?
C2 C3 . 1.538(3) ?
C3 C5 . 1.535(3) ?
C3 C4 . 1.538(3) ?
C3 C6 . 1.543(3) ?
C4 H4A . 0.98 ?
C4 H4B . 0.98 ?
C4 H4C . 0.98 ?
C5 H5A . 0.98 ?
C5 H5B . 0.98 ?
C5 H5C . 0.98 ?
C6 H6A . 0.98 ?
C6 H6B . 0.98 ?
C6 H6C . 0.98 ?
C7 C8 . 1.396(3) ?
C7 H7 . 0.95 ?
C8 C9 . 1.377(3) ?
C8 H8 . 0.95 ?
C9 C10 . 1.403(3) ?
C9 H9 . 0.95 ?
C10 C11 . 1.446(3) ?
C11 N1 . 1.286(2) ?
C11 H11 . 0.95 ?
C12 N1 . 1.477(2) ?
C12 C13 . 1.524(3) ?
C12 H12A . 0.99 ?
C12 H12B . 0.99 ?
C13 C14 . 1.517(3) ?
C13 H13A . 0.99 ?
C13 H13B . 0.99 ?
C14 O3 . 1.429(2) ?
C14 H14A . 0.99 ?
C14 H14B . 0.99 ?
C15 O4 . 1.407(2) ?
C15 H15A . 0.98 ?
C15 H15B . 0.98 ?
C15 H15C . 0.98 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
O1 V1 O3 . . 103.46(8) ?
O1 V1 O4 . . 107.70(8) ?
O3 V1 O4 . . 92.31(7) ?
O1 V1 O2 . . 110.70(8) ?
O3 V1 O2 . . 144.24(8) ?
O4 V1 O2 . . 87.28(6) ?
O1 V1 N1 . . 96.68(7) ?
O3 V1 N1 . . 84.33(6) ?
O4 V1 N1 . . 155.48(7) ?
O2 V1 N1 . . 81.58(6) ?
O2 C1 C10 . . 119.27(16) ?
O2 C1 C2 . . 119.95(16) ?
C10 C1 C2 . . 120.77(16) ?
C7 C2 C1 . . 116.47(18) ?
C7 C2 C3 . . 122.58(17) ?
C1 C2 C3 . . 120.90(16) ?
C5 C3 C4 . . 109.36(16) ?
C5 C3 C2 . . 111.66(17) ?
C4 C3 C2 . . 109.36(16) ?
C5 C3 C6 . . 107.39(17) ?
C4 C3 C6 . . 108.45(18) ?
C2 C3 C6 . . 110.55(16) ?
C3 C4 H4A . . 109.5 ?
C3 C4 H4B . . 109.5 ?
H4A C4 H4B . . 109.5 ?
C3 C4 H4C . . 109.5 ?
H4A C4 H4C . . 109.5 ?
H4B C4 H4C . . 109.5 ?
C3 C5 H5A . . 109.5 ?
C3 C5 H5B . . 109.5 ?
H5A C5 H5B . . 109.5 ?
C3 C5 H5C . . 109.5 ?
H5A C5 H5C . . 109.5 ?
H5B C5 H5C . . 109.5 ?
C3 C6 H6A . . 109.5 ?
C3 C6 H6B . . 109.5 ?
H6A C6 H6B . . 109.5 ?
C3 C6 H6C . . 109.5 ?
H6A C6 H6C . . 109.5 ?
H6B C6 H6C . . 109.5 ?
C2 C7 C8 . . 123.18(19) ?
C2 C7 H7 . . 118.4 ?
C8 C7 H7 . . 118.4 ?
C9 C8 C7 . . 119.71(19) ?
C9 C8 H8 . . 120.1 ?
C7 C8 H8 . . 120.1 ?
C8 C9 C10 . . 119.64(19) ?
C8 C9 H9 . . 120.2 ?
C10 C9 H9 . . 120.2 ?
C9 C10 C1 . . 120.21(17) ?
C9 C10 C11 . . 118.94(17) ?
C1 C10 C11 . . 120.83(16) ?
N1 C11 C10 . . 126.31(17) ?
N1 C11 H11 . . 116.8 ?
C10 C11 H11 . . 116.8 ?
N1 C12 C13 . . 111.94(16) ?
N1 C12 H12A . . 109.2 ?
C13 C12 H12A . . 109.2 ?
N1 C12 H12B . . 109.2 ?
C13 C12 H12B . . 109.2 ?
H12A C12 H12B . . 107.9 ?
C14 C13 C12 . . 111.68(17) ?
C14 C13 H13A . . 109.3 ?
C12 C13 H13A . . 109.3 ?
C14 C13 H13B . . 109.3 ?
C12 C13 H13B . . 109.3 ?
H13A C13 H13B . . 107.9 ?
O3 C14 C13 . . 109.89(16) ?
O3 C14 H14A . . 109.7 ?
C13 C14 H14A . . 109.7 ?
O3 C14 H14B . . 109.7 ?
C13 C14 H14B . . 109.7 ?
H14A C14 H14B . . 108.2 ?
O4 C15 H15A . . 109.5 ?
O4 C15 H15B . . 109.5 ?
H15A C15 H15B . . 109.5 ?
O4 C15 H15C . . 109.5 ?
H15A C15 H15C . . 109.5 ?
H15B C15 H15C . . 109.5 ?
C11 N1 C12 . . 116.01(17) ?
C11 N1 V1 . . 127.75(14) ?
C12 N1 V1 . . 116.21(12) ?
C1 O2 V1 . . 141.49(12) ?
C14 O3 V1 . . 128.34(13) ?
C15 O4 V1 . . 123.09(13) ?


# start Validation Reply Form
_vrf_PLAT987_I                   
;
PROBLEM: The Flack x is >> 0 -  Do a BASF/TWIN Refinement     Please Check
RESPONSE: Racemic Twinning
;
# end Validation Reply Form
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: methanol'
_chemical_properties_physical    'Light-sensitive, Photo-sensitive'
