# Electronic Supplementary Material (ESI) for RSC Advances.
# 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_H3L3
_database_code_depnum_ccdc_archive 'CCDC 1406044'
_audit_update_record             
;
2015-08-18 deposited with the CCDC.
2015-10-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C17.50 H19 N2 O4.50'
_chemical_formula_weight         329.35

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'

_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                   12.1814(14)
_cell_length_b                   12.8382(18)
_cell_length_c                   13.3641(15)
_cell_angle_alpha                112.586(12)
_cell_angle_beta                 96.537(10)
_cell_angle_gamma                117.044(13)
_cell_volume                     1609.5(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    11378
_cell_measurement_theta_min      3.10
_cell_measurement_theta_max      30.00

_exptl_crystal_description       needle
_exptl_crystal_colour            white
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.03
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.359
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             696
_exptl_absorpt_coefficient_mu    0.099
_exptl_absorpt_correction_type   none

_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_standards_number         n/a
_diffrn_measurement_device       'Oxford Diffaction X-Calibur System'
_diffrn_measurement_method       '321 frames, counting time 10 s.'
_diffrn_standards_interval_count n/a
_diffrn_standards_interval_time  n/a
_diffrn_standards_decay_%        n/a
_diffrn_reflns_number            11378
_diffrn_reflns_av_R_equivalents  0.0532
_diffrn_reflns_av_sigmaI/netI    0.1375
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         3.10
_diffrn_reflns_theta_max         30.00
_reflns_number_total             8976
_reflns_number_gt                5028
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Crysalis, Oxford Diffraction'
_computing_cell_refinement       'Crysalis, Oxford Diffraction'
_computing_data_reduction        'Crysalis, Oxford Diffraction'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    PLATON(Spek,2004)
_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)+(0.0641P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         8976
_refine_ls_number_parameters     441
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1663
_refine_ls_R_factor_gt           0.0940
_refine_ls_wR_factor_ref         0.2107
_refine_ls_wR_factor_gt          0.1706
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_restrained_S_all      1.038
_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
N1A N 0.7266(2) 0.1216(2) 0.5126(2) 0.0175(5) Uani 1 1 d . . .
N2A N 0.7958(2) 0.0886(2) 0.4465(2) 0.0181(5) Uani 1 1 d . . .
HN2A H 0.8135 0.0305 0.4453 0.022 Uiso 1 1 calc R . .
O2A O 0.6243(2) 0.2592(2) 0.5669(2) 0.0223(5) Uani 1 1 d . . .
HO2A H 0.6680 0.2335 0.5356 0.033 Uiso 1 1 calc R . .
O5A O 0.8879(2) -0.0586(2) 0.35670(19) 0.0255(5) Uani 1 1 d . . .
HO5A H 0.9078 -0.1145 0.3418 0.038 Uiso 1 1 calc R . .
O6A O 0.4376(2) 0.0394(2) 0.8400(2) 0.0256(5) Uani 1 1 d . . .
O3A O 0.8152(2) 0.2385(2) 0.39038(19) 0.0219(5) Uani 1 1 d . . .
C1A C 0.5842(3) 0.2024(3) 0.6339(3) 0.0183(6) Uani 1 1 d . . .
C6A C 0.5138(3) 0.2396(3) 0.6979(3) 0.0203(7) Uani 1 1 d . . .
H6A H 0.4978 0.3028 0.6949 0.024 Uiso 1 1 calc R . .
C5A C 0.4671(3) 0.1844(3) 0.7660(3) 0.0203(7) Uani 1 1 d . . .
H5A H 0.4196 0.2100 0.8083 0.024 Uiso 1 1 calc R . .
C4A C 0.4913(3) 0.0901(3) 0.7712(3) 0.0203(7) Uani 1 1 d . . .
C3A C 0.5622(3) 0.0530(3) 0.7094(3) 0.0170(6) Uani 1 1 d . . .
H3A H 0.5778 -0.0100 0.7137 0.020 Uiso 1 1 calc R . .
C2A C 0.6117(3) 0.1082(3) 0.6397(3) 0.0150(6) Uani 1 1 d . . .
C7A C 0.6891(3) 0.0682(3) 0.5767(3) 0.0174(6) Uani 1 1 d . . .
C8A C 0.8355(3) 0.1498(3) 0.3832(3) 0.0160(6) Uani 1 1 d . . .
C9A C 0.8999(3) 0.1036(3) 0.3045(3) 0.0179(6) Uani 1 1 d . . .
C10A C 0.9251(3) 0.0035(3) 0.2926(3) 0.0181(6) Uani 1 1 d . . .
C11A C 0.9875(3) -0.0307(3) 0.2172(3) 0.0217(7) Uani 1 1 d . . .
H11A H 1.0025 -0.0979 0.2090 0.026 Uiso 1 1 calc R . .
C12A C 1.0277(3) 0.0345(3) 0.1537(3) 0.0242(7) Uani 1 1 d . . .
H12A H 1.0700 0.0117 0.1036 0.029 Uiso 1 1 calc R . .
C13A C 1.0042(3) 0.1346(3) 0.1655(3) 0.0263(8) Uani 1 1 d . . .
H13A H 1.0313 0.1793 0.1237 0.032 Uiso 1 1 calc R . .
C14A C 0.9408(3) 0.1667(3) 0.2391(3) 0.0233(7) Uani 1 1 d . . .
H14A H 0.9245 0.2327 0.2455 0.028 Uiso 1 1 calc R . .
C15A C 0.7184(3) -0.0290(3) 0.5897(3) 0.0217(7) Uani 1 1 d . . .
H15A H 0.6387 -0.1164 0.5532 0.033 Uiso 1 1 calc R . .
H15B H 0.7539 0.0011 0.6704 0.033 Uiso 1 1 calc R . .
H15C H 0.7812 -0.0334 0.5538 0.033 Uiso 1 1 calc R . .
C16A C 0.4529(4) -0.0633(3) 0.8417(3) 0.0281(8) Uani 1 1 d . . .
H16A H 0.4140 -0.1378 0.7646 0.042 Uiso 1 1 calc R . .
H16B H 0.4101 -0.0927 0.8903 0.042 Uiso 1 1 calc R . .
H16C H 0.5448 -0.0289 0.8714 0.042 Uiso 1 1 calc R . .
N1B N 0.0612(2) 0.6399(2) 0.2112(2) 0.0160(5) Uani 1 1 d . . .
N2B N 0.0022(2) 0.6107(2) 0.2865(2) 0.0161(5) Uani 1 1 d . . .
HN2B H 0.0012 0.5514 0.3024 0.019 Uiso 1 1 calc R . .
O2B O 0.1063(2) 0.7734(2) 0.10551(19) 0.0232(5) Uani 1 1 d . . .
HO2B H 0.0790 0.7500 0.1513 0.035 Uiso 1 1 calc R . .
O3B O -0.0433(2) 0.7697(2) 0.31911(19) 0.0228(5) Uani 1 1 d . . .
O5B O -0.0922(2) 0.4559(2) 0.37481(19) 0.0234(5) Uani 1 1 d . . .
HO5B H -0.1098 0.3969 0.3922 0.035 Uiso 1 1 calc R . .
O6B O 0.3394(2) 0.5219(2) -0.1201(2) 0.0282(6) Uani 1 1 d . . .
C1B C 0.1627(3) 0.7077(3) 0.0555(3) 0.0181(6) Uani 1 1 d . . .
C6B C 0.2140(3) 0.7353(3) -0.0259(3) 0.0218(7) Uani 1 1 d . . .
H6B H 0.2092 0.7977 -0.0420 0.026 Uiso 1 1 calc R . .
C5B C 0.2715(3) 0.6720(3) -0.0826(3) 0.0214(7) Uani 1 1 d . . .
H5B H 0.3048 0.6914 -0.1368 0.026 Uiso 1 1 calc R . .
C4B C 0.2799(3) 0.5783(3) -0.0588(3) 0.0190(6) Uani 1 1 d . . .
C3B C 0.2308(3) 0.5500(3) 0.0215(3) 0.0181(6) Uani 1 1 d . . .
H3B H 0.2373 0.4882 0.0375 0.022 Uiso 1 1 calc R . .
C2B C 0.1707(3) 0.6131(3) 0.0801(3) 0.0160(6) Uani 1 1 d . . .
C7B C 0.1159(3) 0.5788(3) 0.1640(3) 0.0176(6) Uani 1 1 d . . .
C8B C -0.0539(3) 0.6764(3) 0.3350(3) 0.0170(6) Uani 1 1 d . . .
C9B C -0.1277(3) 0.6333(3) 0.4078(3) 0.0179(6) Uani 1 1 d . . .
C10B C -0.1446(3) 0.5268(3) 0.4262(3) 0.0180(6) Uani 1 1 d . . .
C11B C -0.2143(3) 0.4950(3) 0.4967(3) 0.0228(7) Uani 1 1 d . . .
H11B H -0.2252 0.4246 0.5087 0.027 Uiso 1 1 calc R . .
C12B C -0.2670(3) 0.5664(3) 0.5488(3) 0.0240(7) Uani 1 1 d . . .
H12B H -0.3130 0.5445 0.5960 0.029 Uiso 1 1 calc R . .
C13B C -0.2518(3) 0.6714(3) 0.5309(3) 0.0252(7) Uani 1 1 d . . .
H13B H -0.2876 0.7198 0.5659 0.030 Uiso 1 1 calc R . .
C14B C -0.1833(3) 0.7030(3) 0.4611(3) 0.0216(7) Uani 1 1 d . . .
H14B H -0.1740 0.7729 0.4491 0.026 Uiso 1 1 calc R . .
C15B C 0.1269(3) 0.4769(3) 0.1873(3) 0.0194(6) Uani 1 1 d . . .
H15D H 0.0890 0.4669 0.2447 0.029 Uiso 1 1 calc R . .
H15E H 0.2179 0.5071 0.2148 0.029 Uiso 1 1 calc R . .
H15F H 0.0807 0.3919 0.1171 0.029 Uiso 1 1 calc R . .
C16B C 0.3353(3) 0.4138(3) -0.1103(3) 0.0283(8) Uani 1 1 d . . .
H16D H 0.3810 0.4450 -0.0314 0.042 Uiso 1 1 calc R . .
H16E H 0.3767 0.3804 -0.1591 0.042 Uiso 1 1 calc R . .
H16F H 0.2453 0.3431 -0.1337 0.042 Uiso 1 1 calc R . .
C23 C 0.3427(4) 0.2023(4) 0.0425(3) 0.0435(10) Uani 1 1 d . . .
H23A H 0.2812 0.1932 -0.0172 0.065 Uiso 1 1 calc R . .
H23B H 0.3013 0.1243 0.0516 0.065 Uiso 1 1 calc R . .
H23C H 0.4179 0.2110 0.0215 0.065 Uiso 1 1 calc R . .
C22 C 0.4686(4) 0.3462(4) 0.2603(3) 0.0424(10) Uani 1 1 d . . .
H22A H 0.5513 0.3612 0.2534 0.064 Uiso 1 1 calc R . .
H22B H 0.4241 0.2683 0.2692 0.064 Uiso 1 1 calc R . .
H22C H 0.4836 0.4232 0.3267 0.064 Uiso 1 1 calc R . .
C21 C 0.3854(4) 0.3245(4) 0.1538(3) 0.0312(8) Uani 1 1 d . . .
O21 O 0.3569(3) 0.4046(3) 0.1584(3) 0.0509(8) Uani 1 1 d . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1A C7A 1.292(3) . ?
N1A N2A 1.370(3) . ?
N2A C8A 1.351(3) . ?
N2A HN2A 0.8600 . ?
O2A C1A 1.361(3) . ?
O2A HO2A 0.8200 . ?
O5A C10A 1.364(3) . ?
O5A HO5A 0.8200 . ?
O6A C4A 1.382(3) . ?
O6A C16A 1.421(3) . ?
O3A C8A 1.243(3) . ?
C1A C6A 1.386(4) . ?
C1A C2A 1.419(4) . ?
C6A C5A 1.378(4) . ?
C6A H6A 0.9300 . ?
C5A C4A 1.394(4) . ?
C5A H5A 0.9300 . ?
C4A C3A 1.374(4) . ?
C3A C2A 1.407(4) . ?
C3A H3A 0.9300 . ?
C2A C7A 1.467(4) . ?
C7A C15A 1.507(4) . ?
C8A C9A 1.484(4) . ?
C9A C14A 1.395(4) . ?
C9A C10A 1.409(4) . ?
C10A C11A 1.387(4) . ?
C11A C12A 1.389(4) . ?
C11A H11A 0.9300 . ?
C12A C13A 1.395(4) . ?
C12A H12A 0.9300 . ?
C13A C14A 1.373(4) . ?
C13A H13A 0.9300 . ?
C14A H14A 0.9300 . ?
C15A H15A 0.9600 . ?
C15A H15B 0.9600 . ?
C15A H15C 0.9600 . ?
C16A H16A 0.9600 . ?
C16A H16B 0.9600 . ?
C16A H16C 0.9600 . ?
N1B C7B 1.284(4) . ?
N1B N2B 1.370(3) . ?
N2B C8B 1.343(4) . ?
N2B HN2B 0.8600 . ?
O2B C1B 1.352(3) . ?
O2B HO2B 0.8200 . ?
O3B C8B 1.249(3) . ?
O5B C10B 1.362(3) . ?
O5B HO5B 0.8200 . ?
O6B C4B 1.371(3) . ?
O6B C16B 1.422(3) . ?
C1B C6B 1.397(4) . ?
C1B C2B 1.414(4) . ?
C6B C5B 1.375(4) . ?
C6B H6B 0.9300 . ?
C5B C4B 1.398(4) . ?
C5B H5B 0.9300 . ?
C4B C3B 1.374(4) . ?
C3B C2B 1.410(4) . ?
C3B H3B 0.9300 . ?
C2B C7B 1.476(4) . ?
C7B C15B 1.512(4) . ?
C8B C9B 1.490(4) . ?
C9B C14B 1.392(4) . ?
C9B C10B 1.409(4) . ?
C10B C11B 1.393(4) . ?
C11B C12B 1.372(4) . ?
C11B H11B 0.9300 . ?
C12B C13B 1.393(4) . ?
C12B H12B 0.9300 . ?
C13B C14B 1.375(4) . ?
C13B H13B 0.9300 . ?
C14B H14B 0.9300 . ?
C15B H15D 0.9600 . ?
C15B H15E 0.9600 . ?
C15B H15F 0.9600 . ?
C16B H16D 0.9600 . ?
C16B H16E 0.9600 . ?
C16B H16F 0.9600 . ?
C23 C21 1.494(5) . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 0.9600 . ?
C22 C21 1.496(5) . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
C21 O21 1.210(4) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C7A N1A N2A 120.5(2) . . ?
C8A N2A N1A 118.1(2) . . ?
C8A N2A HN2A 120.9 . . ?
N1A N2A HN2A 120.9 . . ?
C1A O2A HO2A 109.5 . . ?
C10A O5A HO5A 109.5 . . ?
C4A O6A C16A 116.4(2) . . ?
O2A C1A C6A 117.4(3) . . ?
O2A C1A C2A 122.5(3) . . ?
C6A C1A C2A 120.0(3) . . ?
C5A C6A C1A 121.0(3) . . ?
C5A C6A H6A 119.5 . . ?
C1A C6A H6A 119.5 . . ?
C6A C5A C4A 119.6(3) . . ?
C6A C5A H5A 120.2 . . ?
C4A C5A H5A 120.2 . . ?
C3A C4A O6A 125.0(3) . . ?
C3A C4A C5A 120.3(3) . . ?
O6A C4A C5A 114.7(3) . . ?
C4A C3A C2A 121.3(3) . . ?
C4A C3A H3A 119.3 . . ?
C2A C3A H3A 119.3 . . ?
C3A C2A C1A 117.7(3) . . ?
C3A C2A C7A 119.9(2) . . ?
C1A C2A C7A 122.4(3) . . ?
N1A C7A C2A 115.1(2) . . ?
N1A C7A C15A 125.2(3) . . ?
C2A C7A C15A 119.7(3) . . ?
O3A C8A N2A 120.1(3) . . ?
O3A C8A C9A 122.8(3) . . ?
N2A C8A C9A 117.0(2) . . ?
C14A C9A C10A 117.7(3) . . ?
C14A C9A C8A 117.0(3) . . ?
C10A C9A C8A 125.3(3) . . ?
O5A C10A C11A 120.6(2) . . ?
O5A C10A C9A 119.0(3) . . ?
C11A C10A C9A 120.4(3) . . ?
C10A C11A C12A 120.5(3) . . ?
C10A C11A H11A 119.7 . . ?
C12A C11A H11A 119.7 . . ?
C11A C12A C13A 119.6(3) . . ?
C11A C12A H12A 120.2 . . ?
C13A C12A H12A 120.2 . . ?
C14A C13A C12A 119.6(3) . . ?
C14A C13A H13A 120.2 . . ?
C12A C13A H13A 120.2 . . ?
C13A C14A C9A 122.2(3) . . ?
C13A C14A H14A 118.9 . . ?
C9A C14A H14A 118.9 . . ?
C7A C15A H15A 109.5 . . ?
C7A C15A H15B 109.5 . . ?
H15A C15A H15B 109.5 . . ?
C7A C15A H15C 109.5 . . ?
H15A C15A H15C 109.5 . . ?
H15B C15A H15C 109.5 . . ?
O6A C16A H16A 109.5 . . ?
O6A C16A H16B 109.5 . . ?
H16A C16A H16B 109.5 . . ?
O6A C16A H16C 109.5 . . ?
H16A C16A H16C 109.5 . . ?
H16B C16A H16C 109.5 . . ?
C7B N1B N2B 119.9(2) . . ?
C8B N2B N1B 118.8(2) . . ?
C8B N2B HN2B 120.6 . . ?
N1B N2B HN2B 120.6 . . ?
C1B O2B HO2B 109.5 . . ?
C10B O5B HO5B 109.5 . . ?
C4B O6B C16B 117.0(2) . . ?
O2B C1B C6B 117.0(2) . . ?
O2B C1B C2B 123.9(3) . . ?
C6B C1B C2B 119.1(3) . . ?
C5B C6B C1B 121.3(3) . . ?
C5B C6B H6B 119.4 . . ?
C1B C6B H6B 119.4 . . ?
C6B C5B C4B 120.0(3) . . ?
C6B C5B H5B 120.0 . . ?
C4B C5B H5B 120.0 . . ?
O6B C4B C3B 125.2(3) . . ?
O6B C4B C5B 114.9(3) . . ?
C3B C4B C5B 119.8(3) . . ?
C4B C3B C2B 121.1(3) . . ?
C4B C3B H3B 119.4 . . ?
C2B C3B H3B 119.4 . . ?
C3B C2B C1B 118.7(3) . . ?
C3B C2B C7B 120.2(2) . . ?
C1B C2B C7B 121.2(3) . . ?
N1B C7B C2B 115.4(2) . . ?
N1B C7B C15B 125.5(3) . . ?
C2B C7B C15B 119.2(3) . . ?
O3B C8B N2B 120.5(3) . . ?
O3B C8B C9B 122.2(3) . . ?
N2B C8B C9B 117.3(2) . . ?
C14B C9B C10B 118.0(3) . . ?
C14B C9B C8B 117.8(2) . . ?
C10B C9B C8B 124.2(3) . . ?
O5B C10B C11B 120.5(2) . . ?
O5B C10B C9B 119.6(3) . . ?
C11B C10B C9B 119.9(3) . . ?
C12B C11B C10B 120.6(3) . . ?
C12B C11B H11B 119.7 . . ?
C10B C11B H11B 119.7 . . ?
C11B C12B C13B 120.1(3) . . ?
C11B C12B H12B 119.9 . . ?
C13B C12B H12B 119.9 . . ?
C14B C13B C12B 119.4(3) . . ?
C14B C13B H13B 120.3 . . ?
C12B C13B H13B 120.3 . . ?
C13B C14B C9B 121.9(3) . . ?
C13B C14B H14B 119.1 . . ?
C9B C14B H14B 119.1 . . ?
C7B C15B H15D 109.5 . . ?
C7B C15B H15E 109.5 . . ?
H15D C15B H15E 109.5 . . ?
C7B C15B H15F 109.5 . . ?
H15D C15B H15F 109.5 . . ?
H15E C15B H15F 109.5 . . ?
O6B C16B H16D 109.5 . . ?
O6B C16B H16E 109.5 . . ?
H16D C16B H16E 109.5 . . ?
O6B C16B H16F 109.5 . . ?
H16D C16B H16F 109.5 . . ?
H16E C16B H16F 109.5 . . ?
C21 C23 H23A 109.5 . . ?
C21 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
C21 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C21 C22 H22A 109.5 . . ?
C21 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C21 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
O21 C21 C23 122.0(4) . . ?
O21 C21 C22 120.8(4) . . ?
C23 C21 C22 117.2(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
C7A N1A N2A C8A -178.4(3) . . . . ?
O2A C1A C6A C5A 178.6(3) . . . . ?
C2A C1A C6A C5A -1.4(5) . . . . ?
C1A C6A C5A C4A 0.3(5) . . . . ?
C16A O6A C4A C3A -3.0(4) . . . . ?
C16A O6A C4A C5A 176.1(3) . . . . ?
C6A C5A C4A C3A 0.5(5) . . . . ?
C6A C5A C4A O6A -178.7(3) . . . . ?
O6A C4A C3A C2A 178.9(3) . . . . ?
C5A C4A C3A C2A -0.1(5) . . . . ?
C4A C3A C2A C1A -0.9(4) . . . . ?
C4A C3A C2A C7A 178.8(3) . . . . ?
O2A C1A C2A C3A -178.3(3) . . . . ?
C6A C1A C2A C3A 1.7(4) . . . . ?
O2A C1A C2A C7A 2.0(5) . . . . ?
C6A C1A C2A C7A -178.1(3) . . . . ?
N2A N1A C7A C2A -177.8(2) . . . . ?
N2A N1A C7A C15A 1.9(5) . . . . ?
C3A C2A C7A N1A 178.0(3) . . . . ?
C1A C2A C7A N1A -2.2(4) . . . . ?
C3A C2A C7A C15A -1.7(4) . . . . ?
C1A C2A C7A C15A 178.0(3) . . . . ?
N1A N2A C8A O3A 3.7(4) . . . . ?
N1A N2A C8A C9A -174.8(3) . . . . ?
O3A C8A C9A C14A 1.5(5) . . . . ?
N2A C8A C9A C14A 179.9(3) . . . . ?
O3A C8A C9A C10A -179.8(3) . . . . ?
N2A C8A C9A C10A -1.4(5) . . . . ?
C14A C9A C10A O5A 179.1(3) . . . . ?
C8A C9A C10A O5A 0.4(5) . . . . ?
C14A C9A C10A C11A -0.6(5) . . . . ?
C8A C9A C10A C11A -179.2(3) . . . . ?
O5A C10A C11A C12A -178.7(3) . . . . ?
C9A C10A C11A C12A 1.0(5) . . . . ?
C10A C11A C12A C13A -0.4(5) . . . . ?
C11A C12A C13A C14A -0.5(5) . . . . ?
C12A C13A C14A C9A 0.9(5) . . . . ?
C10A C9A C14A C13A -0.3(5) . . . . ?
C8A C9A C14A C13A 178.4(3) . . . . ?
C7B N1B N2B C8B 179.8(3) . . . . ?
O2B C1B C6B C5B -179.0(3) . . . . ?
C2B C1B C6B C5B 0.3(5) . . . . ?
C1B C6B C5B C4B -0.3(5) . . . . ?
C16B O6B C4B C3B 8.2(5) . . . . ?
C16B O6B C4B C5B -172.1(3) . . . . ?
C6B C5B C4B O6B -179.8(3) . . . . ?
C6B C5B C4B C3B -0.1(5) . . . . ?
O6B C4B C3B C2B -179.8(3) . . . . ?
C5B C4B C3B C2B 0.6(5) . . . . ?
C4B C3B C2B C1B -0.5(4) . . . . ?
C4B C3B C2B C7B 178.6(3) . . . . ?
O2B C1B C2B C3B 179.4(3) . . . . ?
C6B C1B C2B C3B 0.1(4) . . . . ?
O2B C1B C2B C7B 0.3(5) . . . . ?
C6B C1B C2B C7B -179.0(3) . . . . ?
N2B N1B C7B C2B 177.1(2) . . . . ?
N2B N1B C7B C15B -2.5(5) . . . . ?
C3B C2B C7B N1B -178.8(3) . . . . ?
C1B C2B C7B N1B 0.3(4) . . . . ?
C3B C2B C7B C15B 0.9(4) . . . . ?
C1B C2B C7B C15B 179.9(3) . . . . ?
N1B N2B C8B O3B -5.7(4) . . . . ?
N1B N2B C8B C9B 174.5(2) . . . . ?
O3B C8B C9B C14B -1.5(5) . . . . ?
N2B C8B C9B C14B 178.3(3) . . . . ?
O3B C8B C9B C10B 178.6(3) . . . . ?
N2B C8B C9B C10B -1.6(4) . . . . ?
C14B C9B C10B O5B 179.5(3) . . . . ?
C8B C9B C10B O5B -0.5(5) . . . . ?
C14B C9B C10B C11B -0.5(5) . . . . ?
C8B C9B C10B C11B 179.4(3) . . . . ?
O5B C10B C11B C12B 179.9(3) . . . . ?
C9B C10B C11B C12B 0.0(5) . . . . ?
C10B C11B C12B C13B 0.3(5) . . . . ?
C11B C12B C13B C14B -0.2(5) . . . . ?
C12B C13B C14B C9B -0.4(5) . . . . ?
C10B C9B C14B C13B 0.7(5) . . . . ?
C8B C9B C14B C13B -179.2(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
N2B HN2B O5B 0.86 1.91 2.588(3) 135.3 .
O2B HO2B N1B 0.82 1.82 2.533(3) 144.3 .
N2A HN2A O5A 0.86 1.92 2.600(3) 135.2 .
O2A HO2A N1A 0.82 1.82 2.535(3) 144.9 .
O5A HO5A O3B 0.82 1.78 2.595(3) 176.4 1_645
O5B HO5B O3A 0.82 1.80 2.597(3) 163.5 1_455

_diffrn_measured_fraction_theta_max 0.958
_diffrn_reflns_theta_full        30.00
_diffrn_measured_fraction_theta_full 0.958
_refine_diff_density_max         0.403
_refine_diff_density_min         -0.353
_refine_diff_density_rms         0.074
####################################################################### 
# 
# 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_1
_database_code_depnum_ccdc_archive 'CCDC 1406045'
_audit_update_record             
;
2015-06-10 deposited with the CCDC.
2015-10-20 downloaded from the CCDC.
;


_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C24 H18 N3 O5 V'
_chemical_formula_weight         479.35

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

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   P21/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                   13.5975(17)
_cell_length_b                   11.4633(19)
_cell_length_c                   14.148(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 105.616(16)
_cell_angle_gamma                90.00
_cell_volume                     2123.9(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    9257
_cell_measurement_theta_min      3.11
_cell_measurement_theta_max      30.00

_exptl_crystal_description       needle
_exptl_crystal_colour            black
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.06

_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.499
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             984
_exptl_absorpt_coefficient_mu    0.510
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   'ABSPACK, Oxford Diffraction Ltd'
_exptl_absorpt_correction_T_min  0.933
_exptl_absorpt_correction_T_max  1.000

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_standards_number         n/a
_diffrn_measurement_device       'Oxford Diffaction X-Calibur System'
_diffrn_measurement_method       '321 frames, counting time 10 s.'
_diffrn_standards_interval_count n/a
_diffrn_standards_interval_time  n/a
_diffrn_standards_decay_%        n/a

_diffrn_reflns_number            9257
_diffrn_reflns_av_R_equivalents  0.0656
_diffrn_reflns_av_sigmaI/netI    0.1352
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         3.11
_diffrn_reflns_theta_max         30.00
_reflns_number_total             5923
_reflns_number_gt                2516
_reflns_threshold_expression     >2sigma(I)


_computing_data_collection       'Crysalis, Oxford Diffraction'
_computing_cell_refinement       'Crysalis, Oxford Diffraction'
_computing_data_reduction        'Crysalis, Oxford Diffraction'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    PLATON(Spek,2004)



_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)+(0.0366P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         5923
_refine_ls_number_parameters     300
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1775
_refine_ls_R_factor_gt           0.0706
_refine_ls_wR_factor_ref         0.1676
_refine_ls_wR_factor_gt          0.1202
_refine_ls_goodness_of_fit_ref   0.939
_refine_ls_restrained_S_all      0.939
_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
V V 0.22280(5) 0.17510(6) 0.23932(5) 0.0458(2) Uani 1 1 d . . .
O1 O 0.2937(2) 0.2843(3) 0.2810(2) 0.0614(8) Uani 1 1 d . . .
O3 O 0.1944(2) 0.1206(2) 0.35998(19) 0.0496(7) Uani 1 1 d . . .
C8 C 0.2520(3) 0.0365(4) 0.4081(3) 0.0436(10) Uani 1 1 d . . .
N2 N 0.3249(2) -0.0116(3) 0.3767(2) 0.0459(8) Uani 1 1 d . . .
N1 N 0.3341(2) 0.0451(3) 0.2915(2) 0.0423(8) Uani 1 1 d . . .
C7 C 0.4085(3) 0.0127(4) 0.2571(3) 0.0451(10) Uani 1 1 d . . .
C2 C 0.4263(3) 0.0722(3) 0.1714(3) 0.0433(10) Uani 1 1 d . . .
C3 C 0.5201(3) 0.0619(4) 0.1477(3) 0.0547(12) Uani 1 1 d . . .
H3 H 0.5717 0.0164 0.1871 0.066 Uiso 1 1 calc R . .
C4 C 0.5368(3) 0.1179(4) 0.0673(3) 0.0567(12) Uani 1 1 d . . .
H4 H 0.6001 0.1121 0.0542 0.068 Uiso 1 1 calc R . .
C5 C 0.4603(3) 0.1822(4) 0.0064(3) 0.0576(12) Uani 1 1 d . . .
H5 H 0.4717 0.2181 -0.0487 0.069 Uiso 1 1 calc R . .
C6 C 0.3676(3) 0.1940(3) 0.0260(3) 0.0484(11) Uani 1 1 d . . .
H6 H 0.3163 0.2379 -0.0157 0.058 Uiso 1 1 calc R . .
C1 C 0.3495(3) 0.1397(3) 0.1092(3) 0.0443(10) Uani 1 1 d . . .
O2 O 0.25647(19) 0.1500(2) 0.12369(19) 0.0498(7) Uani 1 1 d . . .
C9 C 0.2340(3) -0.0051(4) 0.5001(3) 0.0431(10) Uani 1 1 d . . .
C14 C 0.1524(3) 0.0385(4) 0.5317(3) 0.0566(12) Uani 1 1 d . . .
H14 H 0.1090 0.0935 0.4936 0.068 Uiso 1 1 calc R . .
C13 C 0.1352(4) 0.0015(4) 0.6183(4) 0.0704(15) Uani 1 1 d . . .
H13 H 0.0803 0.0307 0.6384 0.084 Uiso 1 1 calc R . .
C12 C 0.2002(4) -0.0794(4) 0.6749(4) 0.0696(14) Uani 1 1 d . . .
H12 H 0.1896 -0.1032 0.7343 0.083 Uiso 1 1 calc R . .
C11 C 0.2788(4) -0.1245(4) 0.6459(3) 0.0600(13) Uani 1 1 d . . .
H11 H 0.3206 -0.1806 0.6843 0.072 Uiso 1 1 calc R . .
C10 C 0.2976(3) -0.0877(4) 0.5590(3) 0.0478(10) Uani 1 1 d . . .
C23 C 0.1180(3) -0.0957(4) 0.1630(3) 0.0490(11) Uani 1 1 d . . .
H23 H 0.1826 -0.1292 0.1830 0.059 Uiso 1 1 calc R . .
C22 C 0.0350(3) -0.1681(4) 0.1202(3) 0.0525(11) Uani 1 1 d . . .
H22 H 0.0447 -0.2476 0.1136 0.063 Uiso 1 1 calc R . .
C21 C -0.0596(3) -0.1211(4) 0.0884(3) 0.0516(11) Uani 1 1 d . . .
H21 H -0.1153 -0.1681 0.0592 0.062 Uiso 1 1 calc R . .
C20 C -0.0733(3) -0.0001(4) 0.0997(3) 0.0404(9) Uani 1 1 d . . .
C19 C -0.1670(3) 0.0596(4) 0.0666(3) 0.0509(11) Uani 1 1 d . . .
H19 H -0.2261 0.0188 0.0359 0.061 Uiso 1 1 calc R . .
C18 C -0.1707(3) 0.1762(4) 0.0797(3) 0.0547(12) Uani 1 1 d . . .
H18 H -0.2334 0.2140 0.0588 0.066 Uiso 1 1 calc R . .
C17 C -0.0834(3) 0.2426(4) 0.1237(3) 0.0490(11) Uani 1 1 d . . .
H17 H -0.0882 0.3230 0.1302 0.059 Uiso 1 1 calc R . .
C16 C 0.0085(3) 0.1873(3) 0.1568(3) 0.0386(9) Uani 1 1 d . . .
C24 C 0.0148(3) 0.0645(3) 0.1444(3) 0.0372(9) Uani 1 1 d . . .
C15 C 0.4774(3) -0.0856(4) 0.3038(3) 0.0618(13) Uani 1 1 d . . .
H15A H 0.5211 -0.0603 0.3655 0.093 Uiso 1 1 calc R . .
H15B H 0.5183 -0.1091 0.2614 0.093 Uiso 1 1 calc R . .
H15C H 0.4369 -0.1504 0.3143 0.093 Uiso 1 1 calc R . .
N3 N 0.1098(2) 0.0180(3) 0.1767(2) 0.0395(8) Uani 1 1 d . . .
O5 O 0.3795(2) -0.1357(3) 0.5360(2) 0.0675(9) Uani 1 1 d . . .
HO5 H 0.3856 -0.1070 0.4848 0.101 Uiso 1 1 calc R . .
O4 O 0.09720(19) 0.2446(2) 0.1969(2) 0.0471(7) Uani 1 1 d . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
V O1 1.593(3) . ?
V O2 1.836(3) . ?
V O4 1.833(3) . ?
V O3 1.952(3) . ?
V N1 2.111(3) . ?
V N3 2.378(3) . ?
O3 C8 1.311(4) . ?
C8 N2 1.312(5) . ?
C8 C9 1.467(5) . ?
N2 N1 1.404(4) . ?
N1 C7 1.290(4) . ?
C7 C2 1.466(5) . ?
C7 C15 1.500(5) . ?
C2 C1 1.403(5) . ?
C2 C3 1.408(5) . ?
C3 C4 1.378(6) . ?
C3 H3 0.9300 . ?
C4 C5 1.373(6) . ?
C4 H4 0.9300 . ?
C5 C6 1.369(5) . ?
C5 H5 0.9300 . ?
C6 C1 1.411(5) . ?
C6 H6 0.9300 . ?
C1 O2 1.340(4) . ?
C9 C14 1.396(5) . ?
C9 C10 1.397(5) . ?
C14 C13 1.374(6) . ?
C14 H14 0.9300 . ?
C13 C12 1.379(6) . ?
C13 H13 0.9300 . ?
C12 C11 1.347(6) . ?
C12 H12 0.9300 . ?
C11 C10 1.388(6) . ?
C11 H11 0.9300 . ?
C10 O5 1.357(5) . ?
C23 N3 1.327(5) . ?
C23 C22 1.401(5) . ?
C23 H23 0.9300 . ?
C22 C21 1.355(5) . ?
C22 H22 0.9300 . ?
C21 C20 1.415(5) . ?
C21 H21 0.9300 . ?
C20 C24 1.405(5) . ?
C20 C19 1.410(5) . ?
C19 C18 1.353(6) . ?
C19 H19 0.9300 . ?
C18 C17 1.406(5) . ?
C18 H18 0.9300 . ?
C17 C16 1.367(5) . ?
C17 H17 0.9300 . ?
C16 O4 1.356(4) . ?
C16 C24 1.425(5) . ?
C24 N3 1.357(4) . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
O5 HO5 0.8200 . ?

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 V O2 100.49(14) . . ?
O1 V O4 101.39(14) . . ?
O2 V O4 102.10(12) . . ?
O1 V O3 99.78(14) . . ?
O2 V O3 152.21(12) . . ?
O4 V O3 92.27(12) . . ?
O1 V N1 96.88(14) . . ?
O2 V N1 82.74(12) . . ?
O4 V N1 159.82(12) . . ?
O3 V N1 76.13(12) . . ?
O1 V N3 177.15(13) . . ?
O2 V N3 80.84(11) . . ?
O4 V N3 75.83(11) . . ?
O3 V N3 79.81(11) . . ?
N1 V N3 85.78(11) . . ?
C8 O3 V 117.3(2) . . ?
O3 C8 N2 122.2(4) . . ?
O3 C8 C9 118.7(4) . . ?
N2 C8 C9 119.1(4) . . ?
C8 N2 N1 110.3(3) . . ?
C7 N1 N2 116.8(3) . . ?
C7 N1 V 129.3(3) . . ?
N2 N1 V 113.9(2) . . ?
N1 C7 C2 119.9(4) . . ?
N1 C7 C15 120.7(4) . . ?
C2 C7 C15 119.4(4) . . ?
C1 C2 C3 117.7(4) . . ?
C1 C2 C7 120.9(4) . . ?
C3 C2 C7 121.3(4) . . ?
C4 C3 C2 121.3(4) . . ?
C4 C3 H3 119.3 . . ?
C2 C3 H3 119.3 . . ?
C5 C4 C3 120.2(4) . . ?
C5 C4 H4 119.9 . . ?
C3 C4 H4 119.9 . . ?
C4 C5 C6 120.6(4) . . ?
C4 C5 H5 119.7 . . ?
C6 C5 H5 119.7 . . ?
C5 C6 C1 120.1(4) . . ?
C5 C6 H6 119.9 . . ?
C1 C6 H6 119.9 . . ?
O2 C1 C6 118.2(4) . . ?
O2 C1 C2 121.8(4) . . ?
C6 C1 C2 120.0(4) . . ?
C1 O2 V 128.5(2) . . ?
C14 C9 C10 118.0(4) . . ?
C14 C9 C8 120.4(4) . . ?
C10 C9 C8 121.6(4) . . ?
C13 C14 C9 121.1(5) . . ?
C13 C14 H14 119.5 . . ?
C9 C14 H14 119.5 . . ?
C14 C13 C12 119.3(5) . . ?
C14 C13 H13 120.4 . . ?
C12 C13 H13 120.4 . . ?
C11 C12 C13 121.2(5) . . ?
C11 C12 H12 119.4 . . ?
C13 C12 H12 119.4 . . ?
C12 C11 C10 120.3(5) . . ?
C12 C11 H11 119.9 . . ?
C10 C11 H11 119.9 . . ?
O5 C10 C11 116.6(4) . . ?
O5 C10 C9 123.3(4) . . ?
C11 C10 C9 120.1(4) . . ?
N3 C23 C22 123.7(4) . . ?
N3 C23 H23 118.1 . . ?
C22 C23 H23 118.1 . . ?
C21 C22 C23 119.4(4) . . ?
C21 C22 H22 120.3 . . ?
C23 C22 H22 120.3 . . ?
C22 C21 C20 119.6(4) . . ?
C22 C21 H21 120.2 . . ?
C20 C21 H21 120.2 . . ?
C24 C20 C21 116.4(4) . . ?
C24 C20 C19 118.6(4) . . ?
C21 C20 C19 124.9(4) . . ?
C18 C19 C20 119.9(4) . . ?
C18 C19 H19 120.1 . . ?
C20 C19 H19 120.1 . . ?
C19 C18 C17 122.5(4) . . ?
C19 C18 H18 118.8 . . ?
C17 C18 H18 118.8 . . ?
C16 C17 C18 119.1(4) . . ?
C16 C17 H17 120.4 . . ?
C18 C17 H17 120.4 . . ?
O4 C16 C17 123.2(4) . . ?
O4 C16 C24 117.0(3) . . ?
C17 C16 C24 119.7(4) . . ?
N3 C24 C20 124.3(4) . . ?
N3 C24 C16 115.4(3) . . ?
C20 C24 C16 120.2(4) . . ?
C7 C15 H15A 109.5 . . ?
C7 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C7 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C23 N3 C24 116.5(3) . . ?
C23 N3 V 136.6(3) . . ?
C24 N3 V 106.8(2) . . ?
C10 O5 HO5 109.5 . . ?
C16 O4 V 124.9(2) . . ?

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
O5 H5 N2 0.82 1.88 2.599(4) 145.6 .

_diffrn_measured_fraction_theta_max 0.957
_diffrn_reflns_theta_full        30.00
_diffrn_measured_fraction_theta_full 0.957
_refine_diff_density_max         0.293
_refine_diff_density_min         -0.339
_refine_diff_density_rms         0.064
####################################################################### 
# 
# 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 1406046'
_audit_update_record             
;
2015-06-10 deposited with the CCDC.
2015-10-20 downloaded from the CCDC.
;


_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C25 H20 N3 O5 V'
_chemical_formula_weight         493.38

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                   8.7713(6)
_cell_length_b                   10.1477(8)
_cell_length_c                   13.3468(9)
_cell_angle_alpha                74.541(7)
_cell_angle_beta                 84.262(6)
_cell_angle_gamma                73.896(7)
_cell_volume                     1099.63(14)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    7857
_cell_measurement_theta_min      3.17
_cell_measurement_theta_max      30.00

_exptl_crystal_description       needle
_exptl_crystal_colour            black
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.05
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.490
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             508
_exptl_absorpt_coefficient_mu    0.495
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   'ABSPACK, Oxford Diffraction Ltd'
_exptl_absorpt_correction_T_min  0.951
_exptl_absorpt_correction_T_max  1.000

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_standards_number         n/a
_diffrn_measurement_device       'Oxford Diffaction X-Calibur System'
_diffrn_measurement_method       '321 frames, counting time 10 s.'
_diffrn_standards_interval_count n/a
_diffrn_standards_interval_time  n/a
_diffrn_standards_decay_%        n/a
_diffrn_reflns_number            7857
_diffrn_reflns_av_R_equivalents  0.0336
_diffrn_reflns_av_sigmaI/netI    0.0880
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         3.17
_diffrn_reflns_theta_max         30.00
_reflns_number_total             6167
_reflns_number_gt                4465
_reflns_threshold_expression     >2sigma(I)


_computing_data_collection       'Crysalis, Oxford Diffraction'
_computing_cell_refinement       'Crysalis, Oxford Diffraction'
_computing_data_reduction        'Crysalis, Oxford Diffraction'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    PLATON(Spek,2004)


_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)+(0.0390P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         6167
_refine_ls_number_parameters     310
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0871
_refine_ls_R_factor_gt           0.0572
_refine_ls_wR_factor_ref         0.1239
_refine_ls_wR_factor_gt          0.1095
_refine_ls_goodness_of_fit_ref   1.003
_refine_ls_restrained_S_all      1.003
_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
C8 C 0.4090(3) 0.0396(2) 0.25529(18) 0.0177(5) Uani 1 1 d . . .
N2 N 0.3793(2) 0.0103(2) 0.35606(15) 0.0182(4) Uani 1 1 d . . .
N1 N 0.2392(2) 0.1054(2) 0.37941(15) 0.0169(4) Uani 1 1 d . . .
C7 C 0.1868(3) 0.0759(2) 0.47575(18) 0.0175(5) Uani 1 1 d . . .
C2 C 0.0482(2) 0.1731(2) 0.51043(18) 0.0173(5) Uani 1 1 d . . .
C3 C -0.0184(3) 0.1355(3) 0.61106(18) 0.0194(5) Uani 1 1 d . . .
H3 H 0.0223 0.0448 0.6525 0.023 Uiso 1 1 calc R . .
C4 C -0.1414(3) 0.2274(3) 0.65102(19) 0.0216(5) Uani 1 1 d . . .
C5 C -0.1998(3) 0.3630(3) 0.5874(2) 0.0240(5) Uani 1 1 d . . .
H5 H -0.2829 0.4267 0.6123 0.029 Uiso 1 1 calc R . .
C6 C -0.1376(3) 0.4050(3) 0.4886(2) 0.0240(5) Uani 1 1 d . . .
H6 H -0.1780 0.4965 0.4484 0.029 Uiso 1 1 calc R . .
C1 C -0.0141(3) 0.3108(2) 0.44856(19) 0.0195(5) Uani 1 1 d . . .
C9 C 0.5546(3) -0.0494(2) 0.21710(18) 0.0184(5) Uani 1 1 d . . .
C14 C 0.5951(3) -0.0172(3) 0.11139(19) 0.0235(5) Uani 1 1 d . . .
H14 H 0.5294 0.0592 0.0666 0.028 Uiso 1 1 calc R . .
C13 C 0.7305(3) -0.0963(3) 0.0716(2) 0.0292(6) Uani 1 1 d . . .
H13 H 0.7553 -0.0738 0.0007 0.035 Uiso 1 1 calc R . .
C12 C 0.8291(3) -0.2099(3) 0.1389(2) 0.0278(6) Uani 1 1 d . . .
H12 H 0.9211 -0.2631 0.1130 0.033 Uiso 1 1 calc R . .
C11 C 0.7917(3) -0.2442(3) 0.2438(2) 0.0233(5) Uani 1 1 d . . .
H11 H 0.8589 -0.3201 0.2881 0.028 Uiso 1 1 calc R . .
C10 C 0.6541(3) -0.1662(3) 0.28412(19) 0.0208(5) Uani 1 1 d . . .
C16 C 0.2112(3) 0.4923(2) 0.09944(18) 0.0177(5) Uani 1 1 d . . .
C17 C 0.1963(3) 0.5952(3) 0.00802(19) 0.0239(5) Uani 1 1 d . . .
H17 H 0.1138 0.6109 -0.0359 0.029 Uiso 1 1 calc R . .
C18 C 0.3074(3) 0.6772(3) -0.0189(2) 0.0280(6) Uani 1 1 d . . .
H18 H 0.2951 0.7486 -0.0802 0.034 Uiso 1 1 calc R . .
C19 C 0.4329(3) 0.6547(3) 0.0426(2) 0.0276(6) Uani 1 1 d . . .
H19 H 0.5060 0.7086 0.0219 0.033 Uiso 1 1 calc R . .
C20 C 0.4509(3) 0.5494(3) 0.1376(2) 0.0228(5) Uani 1 1 d . . .
C21 C 0.5744(3) 0.5169(3) 0.2078(2) 0.0301(6) Uani 1 1 d . . .
H21 H 0.6540 0.5643 0.1923 0.036 Uiso 1 1 calc R . .
C22 C 0.5755(3) 0.4154(3) 0.2986(2) 0.0313(6) Uani 1 1 d . . .
H22 H 0.6558 0.3934 0.3456 0.038 Uiso 1 1 calc R . .
C23 C 0.4551(3) 0.3441(3) 0.3211(2) 0.0253(6) Uani 1 1 d . . .
H23 H 0.4564 0.2771 0.3843 0.030 Uiso 1 1 calc R . .
C24 C 0.3380(3) 0.4695(2) 0.16598(19) 0.0187(5) Uani 1 1 d . . .
C15 C 0.2724(3) -0.0579(3) 0.54959(18) 0.0222(5) Uani 1 1 d . . .
H15A H 0.2806 -0.1370 0.5210 0.033 Uiso 1 1 calc R . .
H15B H 0.2145 -0.0701 0.6149 0.033 Uiso 1 1 calc R . .
H15C H 0.3767 -0.0521 0.5602 0.033 Uiso 1 1 calc R . .
C25 C -0.2033(3) 0.1839(3) 0.7610(2) 0.0275(6) Uani 1 1 d . . .
H25A H -0.1641 0.0833 0.7873 0.041 Uiso 1 1 calc R . .
H25B H -0.3173 0.2090 0.7619 0.041 Uiso 1 1 calc R . .
H25C H -0.1681 0.2315 0.8038 0.041 Uiso 1 1 calc R . .
N3 N 0.3402(2) 0.3679(2) 0.25647(16) 0.0201(4) Uani 1 1 d . . .
O1 O -0.00336(19) 0.19666(18) 0.23882(13) 0.0248(4) Uani 1 1 d . . .
O3 O 0.31619(18) 0.14226(17) 0.19059(12) 0.0196(4) Uani 1 1 d . . .
O2 O 0.04526(18) 0.35753(17) 0.35302(13) 0.0222(4) Uani 1 1 d . . .
O5 O 0.62203(19) -0.20811(19) 0.38762(13) 0.0254(4) Uani 1 1 d . . .
HO5 H 0.5373 -0.1571 0.4025 0.038 Uiso 1 1 calc R . .
O4 O 0.10987(17) 0.40963(17) 0.13198(12) 0.0193(4) Uani 1 1 d . . .
V V 0.13508(4) 0.26413(4) 0.25195(3) 0.01813(11) Uani 1 1 d . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C8 O3 1.298(3) . ?
C8 N2 1.313(3) . ?
C8 C9 1.477(3) . ?
N2 N1 1.402(2) . ?
N1 C7 1.307(3) . ?
N1 V 2.0871(19) . ?
C7 C2 1.460(3) . ?
C7 C15 1.499(3) . ?
C2 C3 1.408(3) . ?
C2 C1 1.409(3) . ?
C3 C4 1.382(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.396(3) . ?
C5 C6 1.380(3) . ?
C5 H5 0.9300 . ?
C6 C1 1.398(3) . ?
C6 H6 0.9300 . ?
C1 O2 1.343(3) . ?
C9 C14 1.393(3) . ?
C9 C10 1.408(3) . ?
C14 C13 1.382(3) . ?
C14 H14 0.9300 . ?
C13 C12 1.392(4) . ?
C13 H13 0.9300 . ?
C12 C11 1.379(4) . ?
C12 H12 0.9300 . ?
C11 C10 1.393(3) . ?
C11 H11 0.9300 . ?
C10 O5 1.358(3) . ?
C16 O4 1.351(3) . ?
C16 C17 1.369(3) . ?
C16 C24 1.423(3) . ?
C17 C18 1.411(3) . ?
C17 H17 0.9300 . ?
C18 C19 1.371(4) . ?
C18 H18 0.9300 . ?
C19 C20 1.413(4) . ?
C19 H19 0.9300 . ?
C20 C24 1.410(3) . ?
C20 C21 1.415(4) . ?
C21 C22 1.364(4) . ?
C21 H21 0.9300 . ?
C22 C23 1.404(3) . ?
C22 H22 0.9300 . ?
C23 N3 1.321(3) . ?
C23 H23 0.9300 . ?
C24 N3 1.361(3) . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C25 H25A 0.9600 . ?
C25 H25B 0.9600 . ?
C25 H25C 0.9600 . ?
N3 V 2.336(2) . ?
O1 V 1.5943(17) . ?
O3 V 1.9783(16) . ?
O2 V 1.8421(17) . ?
O5 HO5 0.8200 . ?
O4 V 1.8499(16) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O3 C8 N2 122.4(2) . . ?
O3 C8 C9 120.4(2) . . ?
N2 C8 C9 117.2(2) . . ?
C8 N2 N1 110.07(19) . . ?
C7 N1 N2 115.51(19) . . ?
C7 N1 V 129.41(15) . . ?
N2 N1 V 114.86(14) . . ?
N1 C7 C2 120.1(2) . . ?
N1 C7 C15 118.9(2) . . ?
C2 C7 C15 120.9(2) . . ?
C3 C2 C1 118.0(2) . . ?
C3 C2 C7 120.4(2) . . ?
C1 C2 C7 121.4(2) . . ?
C4 C3 C2 122.9(2) . . ?
C4 C3 H3 118.6 . . ?
C2 C3 H3 118.6 . . ?
C3 C4 C5 117.4(2) . . ?
C3 C4 C25 120.7(2) . . ?
C5 C4 C25 121.9(2) . . ?
C6 C5 C4 121.8(2) . . ?
C6 C5 H5 119.1 . . ?
C4 C5 H5 119.1 . . ?
C5 C6 C1 120.3(2) . . ?
C5 C6 H6 119.8 . . ?
C1 C6 H6 119.8 . . ?
O2 C1 C6 118.2(2) . . ?
O2 C1 C2 122.2(2) . . ?
C6 C1 C2 119.5(2) . . ?
C14 C9 C10 118.8(2) . . ?
C14 C9 C8 119.1(2) . . ?
C10 C9 C8 122.1(2) . . ?
C13 C14 C9 121.5(2) . . ?
C13 C14 H14 119.2 . . ?
C9 C14 H14 119.2 . . ?
C14 C13 C12 119.1(2) . . ?
C14 C13 H13 120.5 . . ?
C12 C13 H13 120.5 . . ?
C11 C12 C13 120.6(2) . . ?
C11 C12 H12 119.7 . . ?
C13 C12 H12 119.7 . . ?
C12 C11 C10 120.6(2) . . ?
C12 C11 H11 119.7 . . ?
C10 C11 H11 119.7 . . ?
O5 C10 C11 117.6(2) . . ?
O5 C10 C9 123.0(2) . . ?
C11 C10 C9 119.4(2) . . ?
O4 C16 C17 123.5(2) . . ?
O4 C16 C24 116.8(2) . . ?
C17 C16 C24 119.7(2) . . ?
C16 C17 C18 119.4(2) . . ?
C16 C17 H17 120.3 . . ?
C18 C17 H17 120.3 . . ?
C19 C18 C17 122.0(2) . . ?
C19 C18 H18 119.0 . . ?
C17 C18 H18 119.0 . . ?
C18 C19 C20 119.8(2) . . ?
C18 C19 H19 120.1 . . ?
C20 C19 H19 120.1 . . ?
C24 C20 C19 118.4(2) . . ?
C24 C20 C21 116.5(2) . . ?
C19 C20 C21 125.1(2) . . ?
C22 C21 C20 119.3(2) . . ?
C22 C21 H21 120.4 . . ?
C20 C21 H21 120.4 . . ?
C21 C22 C23 119.9(2) . . ?
C21 C22 H22 120.1 . . ?
C23 C22 H22 120.1 . . ?
N3 C23 C22 122.9(3) . . ?
N3 C23 H23 118.5 . . ?
C22 C23 H23 118.5 . . ?
N3 C24 C20 123.9(2) . . ?
N3 C24 C16 115.4(2) . . ?
C20 C24 C16 120.7(2) . . ?
C7 C15 H15A 109.5 . . ?
C7 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C7 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C4 C25 H25A 109.5 . . ?
C4 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
C4 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
C23 N3 C24 117.5(2) . . ?
C23 N3 V 135.05(18) . . ?
C24 N3 V 107.31(15) . . ?
C8 O3 V 116.60(14) . . ?
C1 O2 V 131.18(15) . . ?
C10 O5 HO5 109.5 . . ?
C16 O4 V 123.75(14) . . ?
O1 V O2 100.57(8) . . ?
O1 V O4 99.67(8) . . ?
O2 V O4 102.62(7) . . ?
O1 V O3 99.95(8) . . ?
O2 V O3 151.86(7) . . ?
O4 V O3 92.66(7) . . ?
O1 V N1 96.79(8) . . ?
O2 V N1 82.82(7) . . ?
O4 V N1 161.34(7) . . ?
O3 V N1 75.80(7) . . ?
O1 V N3 175.34(8) . . ?
O2 V N3 82.84(7) . . ?
O4 V N3 76.38(7) . . ?
O3 V N3 77.93(7) . . ?
N1 V N3 86.75(7) . . ?

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
O5 HO5 N2 0.82 1.87 2.585(2) 145.3 .

_diffrn_measured_fraction_theta_max 0.960
_diffrn_reflns_theta_full        30.00
_diffrn_measured_fraction_theta_full 0.960
_refine_diff_density_max         0.402
_refine_diff_density_min         -0.418
_refine_diff_density_rms         0.077
####################################################################### 
# 
# 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_3
_database_code_depnum_ccdc_archive 'CCDC 1406047'
_audit_update_record             
;
2015-06-10 deposited with the CCDC.
2015-10-20 downloaded from the CCDC.
;


_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C25 H20 N3 O6 V'
_chemical_formula_weight         509.38

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

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_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                   7.668(3)
_cell_length_b                   14.153(6)
_cell_length_c                   21.853(10)
_cell_angle_alpha                90.00
_cell_angle_beta                 96.860(6)
_cell_angle_gamma                90.00
_cell_volume                     2354.5(18)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    2751
_cell_measurement_theta_min      2.37
_cell_measurement_theta_max      27.61

_exptl_crystal_description       block
_exptl_crystal_colour            black
_exptl_crystal_size_max          .20
_exptl_crystal_size_mid          .18
_exptl_crystal_size_min          .16
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.437
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1048
_exptl_absorpt_coefficient_mu    0.468
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  .911
_exptl_absorpt_correction_T_max  .928
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            15877
_diffrn_reflns_av_R_equivalents  0.1013
_diffrn_reflns_av_sigmaI/netI    0.0952
_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       -25
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         1.72
_diffrn_reflns_theta_max         25.00
_reflns_number_total             4134
_reflns_number_gt                2414
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    '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)+(0.0920P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4134
_refine_ls_number_parameters     319
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1241
_refine_ls_R_factor_gt           0.0662
_refine_ls_wR_factor_ref         0.1767
_refine_ls_wR_factor_gt          0.1503
_refine_ls_goodness_of_fit_ref   0.964
_refine_ls_restrained_S_all      0.964
_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
V V 0.35249(11) 0.76473(5) 0.02576(3) 0.0405(3) Uani 1 1 d . . .
N3 N 0.1019(5) 0.8144(3) 0.07076(16) 0.0435(10) Uani 1 1 d . . .
C20 C -0.0135(7) 0.9671(4) 0.1024(2) 0.0514(13) Uani 1 1 d . . .
C16 C 0.2460(6) 0.9540(3) 0.04489(19) 0.0428(12) Uani 1 1 d . . .
C17 C 0.2587(7) 1.0515(3) 0.0425(2) 0.0541(14) Uani 1 1 d . . .
H17 H 0.3468 1.0803 0.0233 0.065 Uiso 1 1 calc R . .
C24 C 0.1087(6) 0.9110(3) 0.0737(2) 0.0411(11) Uani 1 1 d . . .
C18 C 0.1330(8) 1.1069(4) 0.0700(2) 0.0602(15) Uani 1 1 d . . .
H18 H 0.1404 1.1724 0.0681 0.072 Uiso 1 1 calc R . .
C19 C 0.0027(7) 1.0678(4) 0.0991(2) 0.0593(15) Uani 1 1 d . . .
H19 H -0.0757 1.1064 0.1167 0.071 Uiso 1 1 calc R . .
C23 C -0.0235(7) 0.7721(4) 0.0963(3) 0.0582(14) Uani 1 1 d . . .
H23 H -0.0314 0.7066 0.0936 0.070 Uiso 1 1 calc R . .
C22 C -0.1470(8) 0.8205(4) 0.1277(3) 0.0727(17) Uani 1 1 d . . .
H22 H -0.2311 0.7873 0.1463 0.087 Uiso 1 1 calc R . .
C21 C -0.1409(8) 0.9182(4) 0.1304(3) 0.0701(16) Uani 1 1 d . . .
H21 H -0.2216 0.9512 0.1507 0.084 Uiso 1 1 calc R . .
O4 O 0.3562(4) 0.8951(2) 0.01901(13) 0.0445(8) Uani 1 1 d . . .
O1 O 0.5301(4) 0.7387(2) -0.00152(14) 0.0511(9) Uani 1 1 d . . .
O2 O 0.1853(5) 0.7277(2) -0.03830(13) 0.0501(9) Uani 1 1 d . . .
C1 C 0.1856(6) 0.6463(3) -0.07074(19) 0.0427(12) Uani 1 1 d . . .
C2 C 0.2334(6) 0.5590(3) -0.04249(18) 0.0378(11) Uani 1 1 d . . .
C4 C 0.1822(6) 0.4823(3) -0.1434(2) 0.0461(12) Uani 1 1 d . . .
C3 C 0.2333(6) 0.4772(3) -0.0800(2) 0.0426(12) Uani 1 1 d . . .
H3 H 0.2676 0.4195 -0.0621 0.051 Uiso 1 1 calc R . .
C6 C 0.1281(7) 0.6487(3) -0.1340(2) 0.0548(14) Uani 1 1 d . . .
H6 H 0.0905 0.7056 -0.1523 0.066 Uiso 1 1 calc R . .
C5 C 0.1262(7) 0.5676(4) -0.1702(2) 0.0581(15) Uani 1 1 d . . .
H5 H 0.0875 0.5706 -0.2122 0.070 Uiso 1 1 calc R . .
C25 C 0.1267(8) 0.3977(4) -0.2395(2) 0.082(2) Uani 1 1 d . . .
H25A H 0.0074 0.4197 -0.2448 0.123 Uiso 1 1 calc R . .
H25B H 0.1311 0.3345 -0.2552 0.123 Uiso 1 1 calc R . .
H25C H 0.1976 0.4384 -0.2615 0.123 Uiso 1 1 calc R . .
O6 O 0.1922(5) 0.3984(2) -0.17531(14) 0.0639(10) Uani 1 1 d . . .
C7 C 0.2690(6) 0.5504(3) 0.02523(19) 0.0378(11) Uani 1 1 d . . .
C15 C 0.2578(6) 0.4559(3) 0.0568(2) 0.0474(13) Uani 1 1 d . . .
H15A H 0.3741 0.4329 0.0698 0.071 Uiso 1 1 calc R . .
H15B H 0.1969 0.4117 0.0285 0.071 Uiso 1 1 calc R . .
H15C H 0.1952 0.4630 0.0920 0.071 Uiso 1 1 calc R . .
N2 N 0.3343(5) 0.6165(2) 0.12303(14) 0.0388(9) Uani 1 1 d . . .
N1 N 0.3092(5) 0.6270(2) 0.05862(14) 0.0379(9) Uani 1 1 d . . .
C8 C 0.4007(6) 0.6966(3) 0.14758(19) 0.0388(11) Uani 1 1 d . . .
C9 C 0.4380(6) 0.7047(3) 0.21546(19) 0.0417(12) Uani 1 1 d . . .
C14 C 0.4969(7) 0.7921(4) 0.2408(2) 0.0554(14) Uani 1 1 d . . .
H14 H 0.5087 0.8432 0.2149 0.067 Uiso 1 1 calc R . .
C10 C 0.4184(7) 0.6282(4) 0.2551(2) 0.0489(13) Uani 1 1 d . . .
C11 C 0.4586(7) 0.6393(4) 0.3187(2) 0.0629(15) Uani 1 1 d . . .
H11 H 0.4462 0.5887 0.3450 0.075 Uiso 1 1 calc R . .
C12 C 0.5171(8) 0.7262(4) 0.3425(2) 0.0708(17) Uani 1 1 d . . .
H12 H 0.5431 0.7334 0.3849 0.085 Uiso 1 1 calc R . .
C13 C 0.5374(8) 0.8028(4) 0.3039(2) 0.0729(18) Uani 1 1 d . . .
H13 H 0.5778 0.8606 0.3203 0.087 Uiso 1 1 calc R . .
O5 O 0.3617(6) 0.5411(3) 0.23385(15) 0.0743(12) Uani 1 1 d . . .
HO5 H 0.3502 0.5410 0.1961 0.111 Uiso 1 1 calc R . .
O3 O 0.4358(4) 0.7696(2) 0.11446(12) 0.0415(8) Uani 1 1 d . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
V O1 1.594(3) . ?
V O4 1.851(3) . ?
V O2 1.857(3) . ?
V O3 1.968(3) . ?
V N1 2.117(4) . ?
V N3 2.367(4) . ?
N3 C23 1.312(6) . ?
N3 C24 1.370(5) . ?
C20 C21 1.396(7) . ?
C20 C24 1.428(6) . ?
C20 C19 1.433(7) . ?
C16 O4 1.357(5) . ?
C16 C17 1.386(6) . ?
C16 C24 1.426(6) . ?
C17 C18 1.430(7) . ?
C18 C19 1.363(7) . ?
C23 C22 1.412(7) . ?
C22 C21 1.383(7) . ?
O2 C1 1.353(5) . ?
C1 C6 1.401(6) . ?
C1 C2 1.409(6) . ?
C2 C3 1.419(6) . ?
C2 C7 1.478(6) . ?
C4 O6 1.384(5) . ?
C4 C5 1.388(6) . ?
C4 C3 1.395(6) . ?
C6 C5 1.392(6) . ?
C25 O6 1.432(5) . ?
C7 N1 1.323(5) . ?
C7 C15 1.512(6) . ?
N2 C8 1.330(5) . ?
N2 N1 1.406(4) . ?
C8 O3 1.307(5) . ?
C8 C9 1.481(6) . ?
C9 C10 1.405(6) . ?
C9 C14 1.408(6) . ?
C14 C13 1.384(6) . ?
C10 O5 1.370(5) . ?
C10 C11 1.398(6) . ?
C11 C12 1.389(7) . ?
C12 C13 1.396(7) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 V O4 100.27(15) . . ?
O1 V O2 101.34(16) . . ?
O4 V O2 103.72(13) . . ?
O1 V O3 100.67(15) . . ?
O4 V O3 92.15(12) . . ?
O2 V O3 149.97(15) . . ?
O1 V N1 95.14(15) . . ?
O4 V N1 161.64(13) . . ?
O2 V N1 82.76(13) . . ?
O3 V N1 75.13(12) . . ?
O1 V N3 175.04(15) . . ?
O4 V N3 76.01(14) . . ?
O2 V N3 82.86(14) . . ?
O3 V N3 76.38(13) . . ?
N1 V N3 87.98(14) . . ?
C23 N3 C24 117.5(4) . . ?
C23 N3 V 135.5(3) . . ?
C24 N3 V 106.7(3) . . ?
C21 C20 C24 116.6(5) . . ?
C21 C20 C19 125.8(5) . . ?
C24 C20 C19 117.7(5) . . ?
O4 C16 C17 123.1(5) . . ?
O4 C16 C24 116.9(4) . . ?
C17 C16 C24 120.0(4) . . ?
C16 C17 C18 118.4(5) . . ?
N3 C24 C16 115.5(4) . . ?
N3 C24 C20 123.5(4) . . ?
C16 C24 C20 121.0(4) . . ?
C19 C18 C17 122.8(5) . . ?
C18 C19 C20 120.0(5) . . ?
N3 C23 C22 123.6(5) . . ?
C21 C22 C23 119.0(5) . . ?
C22 C21 C20 119.9(5) . . ?
C16 O4 V 124.2(3) . . ?
C1 O2 V 126.2(3) . . ?
O2 C1 C6 118.5(4) . . ?
O2 C1 C2 122.2(4) . . ?
C6 C1 C2 119.2(4) . . ?
C1 C2 C3 118.7(4) . . ?
C1 C2 C7 121.2(4) . . ?
C3 C2 C7 119.9(4) . . ?
O6 C4 C5 124.5(4) . . ?
O6 C4 C3 115.5(4) . . ?
C5 C4 C3 120.0(4) . . ?
C4 C3 C2 120.8(4) . . ?
C5 C6 C1 121.4(4) . . ?
C4 C5 C6 119.7(4) . . ?
C4 O6 C25 117.8(4) . . ?
N1 C7 C2 119.2(4) . . ?
N1 C7 C15 119.7(4) . . ?
C2 C7 C15 121.1(4) . . ?
C8 N2 N1 108.3(3) . . ?
C7 N1 N2 117.4(3) . . ?
C7 N1 V 127.1(3) . . ?
N2 N1 V 115.4(2) . . ?
O3 C8 N2 123.0(4) . . ?
O3 C8 C9 117.8(4) . . ?
N2 C8 C9 119.2(4) . . ?
C10 C9 C14 119.2(4) . . ?
C10 C9 C8 122.4(4) . . ?
C14 C9 C8 118.4(4) . . ?
C13 C14 C9 120.8(5) . . ?
O5 C10 C11 117.5(4) . . ?
O5 C10 C9 122.5(4) . . ?
C11 C10 C9 120.0(5) . . ?
C12 C11 C10 119.7(5) . . ?
C11 C12 C13 121.1(5) . . ?
C14 C13 C12 119.3(5) . . ?
C8 O3 V 117.0(3) . . ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.342
_refine_diff_density_min         -0.595
_refine_diff_density_rms         0.080
####################################################################### 
# 
# 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_4
_database_code_depnum_ccdc_archive 'CCDC 1406048'
_audit_update_record             
;
2015-06-10 deposited with the CCDC.
2015-10-20 downloaded from the CCDC.
;


_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C24 H17 Cl N3 O5 V'
_chemical_formula_weight         513.80

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'
Cl Cl 0.1484 0.1585 '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                   8.3143(6)
_cell_length_b                   11.3015(7)
_cell_length_c                   12.1012(8)
_cell_angle_alpha                72.559(6)
_cell_angle_beta                 84.859(6)
_cell_angle_gamma                76.042(6)
_cell_volume                     1052.60(12)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    7495
_cell_measurement_theta_min      3.11
_cell_measurement_theta_max      30.00


_exptl_crystal_description       needle
_exptl_crystal_colour            black
_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.04


_exptl_crystal_density_diffrn    1.621
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             524
_exptl_absorpt_coefficient_mu    0.643

_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   'ABSPACK, Oxford Diffraction Ltd'
_exptl_absorpt_correction_T_min  0.936
_exptl_absorpt_correction_T_max  1.000

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_standards_number         n/a
_diffrn_measurement_device       'Oxford Diffaction X-Calibur System'
_diffrn_measurement_method       '321 frames, counting time 10 s.'
_diffrn_standards_interval_count n/a
_diffrn_standards_interval_time  n/a
_diffrn_standards_decay_%        n/a

_diffrn_reflns_number            7495
_diffrn_reflns_av_R_equivalents  0.0269
_diffrn_reflns_av_sigmaI/netI    0.0757
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         3.11
_diffrn_reflns_theta_max         30.00
_reflns_number_total             5889
_reflns_number_gt                4435
_reflns_threshold_expression     >2sigma(I)


_computing_data_collection       'Crysalis, Oxford Diffraction'
_computing_cell_refinement       'Crysalis, Oxford Diffraction'
_computing_data_reduction        'Crysalis, Oxford Diffraction'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    PLATON(Spek,2004)

_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)+(0.0946P)²+1.3561P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         5889
_refine_ls_number_parameters     309
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0751
_refine_ls_R_factor_gt           0.0506
_refine_ls_wR_factor_ref         0.1513
_refine_ls_wR_factor_gt          0.1275
_refine_ls_goodness_of_fit_ref   0.810
_refine_ls_restrained_S_all      0.810
_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
C1 C 0.0806(3) 0.2670(2) 0.7159(2) 0.0145(5) Uani 1 1 d . . .
C6 C -0.0033(3) 0.3799(3) 0.6395(2) 0.0214(5) Uani 1 1 d . . .
H6 H -0.0390 0.3786 0.5693 0.026 Uiso 1 1 calc R . .
C5 C -0.0336(4) 0.4928(3) 0.6669(2) 0.0233(6) Uani 1 1 d . . .
H5 H -0.0903 0.5675 0.6158 0.028 Uiso 1 1 calc R . .
C4 C 0.0208(3) 0.4951(2) 0.7712(2) 0.0186(5) Uani 1 1 d . . .
C3 C 0.0981(3) 0.3844(2) 0.8499(2) 0.0157(5) Uani 1 1 d . . .
H3 H 0.1312 0.3871 0.9203 0.019 Uiso 1 1 calc R . .
C2 C 0.1274(3) 0.2675(2) 0.8249(2) 0.0138(4) Uani 1 1 d . . .
C7 C 0.2071(3) 0.1509(2) 0.9108(2) 0.0136(4) Uani 1 1 d . . .
C8 C 0.2551(3) -0.1682(2) 0.9685(2) 0.0146(5) Uani 1 1 d . . .
C24 C 0.3659(3) -0.1211(2) 0.6191(2) 0.0122(4) Uani 1 1 d . . .
C9 C 0.3215(3) -0.2908(2) 1.0539(2) 0.0161(5) Uani 1 1 d . . .
C14 C 0.2997(3) -0.4037(3) 1.0386(3) 0.0215(5) Uani 1 1 d . . .
H14 H 0.2388 -0.4003 0.9765 0.026 Uiso 1 1 calc R . .
C13 C 0.3679(4) -0.5207(3) 1.1149(3) 0.0275(6) Uani 1 1 d . . .
H13 H 0.3518 -0.5954 1.1047 0.033 Uiso 1 1 calc R . .
C12 C 0.4601(4) -0.5252(3) 1.2062(3) 0.0288(7) Uani 1 1 d . . .
H12 H 0.5083 -0.6037 1.2563 0.035 Uiso 1 1 calc R . .
C11 C 0.4819(4) -0.4165(3) 1.2244(2) 0.0250(6) Uani 1 1 d . . .
H11 H 0.5437 -0.4217 1.2868 0.030 Uiso 1 1 calc R . .
C10 C 0.4117(3) -0.2977(2) 1.1497(2) 0.0178(5) Uani 1 1 d . . .
C16 C 0.2055(3) -0.1305(2) 0.5976(2) 0.0143(5) Uani 1 1 d . . .
C17 C 0.1861(3) -0.1896(2) 0.5171(2) 0.0182(5) Uani 1 1 d . . .
H17 H 0.0812 -0.1955 0.5017 0.022 Uiso 1 1 calc R . .
C18 C 0.3271(4) -0.2410(3) 0.4581(2) 0.0224(6) Uani 1 1 d . . .
H18 H 0.3138 -0.2815 0.4041 0.027 Uiso 1 1 calc R . .
C19 C 0.4825(3) -0.2329(3) 0.4781(2) 0.0203(5) Uani 1 1 d . . .
H19 H 0.5732 -0.2674 0.4378 0.024 Uiso 1 1 calc R . .
C20 C 0.5060(3) -0.1720(2) 0.5602(2) 0.0155(5) Uani 1 1 d . . .
C21 C 0.6590(3) -0.1534(2) 0.5851(2) 0.0178(5) Uani 1 1 d . . .
H21 H 0.7558 -0.1852 0.5485 0.021 Uiso 1 1 calc R . .
C22 C 0.6649(3) -0.0886(2) 0.6628(2) 0.0173(5) Uani 1 1 d . . .
H22 H 0.7655 -0.0764 0.6799 0.021 Uiso 1 1 calc R . .
C23 C 0.5171(3) -0.0405(2) 0.7167(2) 0.0158(5) Uani 1 1 d . . .
H23 H 0.5220 0.0050 0.7684 0.019 Uiso 1 1 calc R . .
C15 C 0.2817(3) 0.1600(2) 1.0148(2) 0.0183(5) Uani 1 1 d . . .
H15A H 0.1989 0.1622 1.0752 0.027 Uiso 1 1 calc R . .
H15B H 0.3229 0.2363 0.9948 0.027 Uiso 1 1 calc R . .
H15C H 0.3713 0.0873 1.0412 0.027 Uiso 1 1 calc R . .
N1 N 0.2063(3) 0.04123(19) 0.89730(17) 0.0134(4) Uani 1 1 d . . .
N2 N 0.2822(3) -0.06488(19) 0.98330(18) 0.0143(4) Uani 1 1 d . . .
N3 N 0.3714(2) -0.05719(19) 0.69688(18) 0.0133(4) Uani 1 1 d . . .
O1 O -0.0880(2) 0.03205(18) 0.80517(16) 0.0200(4) Uani 1 1 d . . .
O2 O 0.1206(2) 0.16130(17) 0.68178(15) 0.0166(4) Uani 1 1 d . . .
O3 O 0.1726(2) -0.16585(16) 0.88114(15) 0.0160(4) Uani 1 1 d . . .
O5 O 0.4360(3) -0.19417(18) 1.17366(17) 0.0224(4) Uani 1 1 d . . .
H55 H 0.3896 -0.1297 1.1253 0.034 Uiso 1 1 calc R . .
O4 O 0.0773(2) -0.07490(17) 0.65396(15) 0.0147(3) Uani 1 1 d . . .
V V 0.10064(5) -0.00119(4) 0.76661(4) 0.01296(12) Uani 1 1 d . . .
Cl Cl -0.00613(9) 0.63864(6) 0.80225(6) 0.02612(17) Uani 1 1 d . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 O2 1.336(3) . ?
C1 C6 1.395(4) . ?
C1 C2 1.411(3) . ?
C6 C5 1.374(4) . ?
C5 C4 1.388(4) . ?
C4 C3 1.375(4) . ?
C4 Cl 1.732(3) . ?
C3 C2 1.402(3) . ?
C2 C7 1.463(3) . ?
C7 N1 1.300(3) . ?
C7 C15 1.492(3) . ?
C8 O3 1.301(3) . ?
C8 N2 1.307(3) . ?
C8 C9 1.472(3) . ?
C24 N3 1.357(3) . ?
C24 C20 1.404(3) . ?
C24 C16 1.416(3) . ?
C9 C14 1.399(4) . ?
C9 C10 1.409(4) . ?
C14 C13 1.387(4) . ?
C13 C12 1.383(5) . ?
C12 C11 1.366(4) . ?
C11 C10 1.397(4) . ?
C10 O5 1.350(3) . ?
C16 O4 1.342(3) . ?
C16 C17 1.374(3) . ?
C17 C18 1.412(4) . ?
C18 C19 1.365(4) . ?
C19 C20 1.416(4) . ?
C20 C21 1.411(3) . ?
C21 C22 1.364(4) . ?
C22 C23 1.407(4) . ?
C23 N3 1.323(3) . ?
N1 N2 1.387(3) . ?
N1 V 2.100(2) . ?
N3 V 2.339(2) . ?
O1 V 1.5841(19) . ?
O2 V 1.8548(18) . ?
O3 V 1.9512(18) . ?
O4 V 1.8428(18) . ?

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
O2 C1 C6 118.8(2) . . ?
O2 C1 C2 121.4(2) . . ?
C6 C1 C2 119.7(2) . . ?
C5 C6 C1 120.7(3) . . ?
C6 C5 C4 119.7(3) . . ?
C3 C4 C5 120.6(2) . . ?
C3 C4 Cl 119.5(2) . . ?
C5 C4 Cl 119.8(2) . . ?
C4 C3 C2 120.6(2) . . ?
C3 C2 C1 118.4(2) . . ?
C3 C2 C7 119.6(2) . . ?
C1 C2 C7 122.0(2) . . ?
N1 C7 C2 119.3(2) . . ?
N1 C7 C15 121.2(2) . . ?
C2 C7 C15 119.4(2) . . ?
O3 C8 N2 122.2(2) . . ?
O3 C8 C9 119.6(2) . . ?
N2 C8 C9 118.3(2) . . ?
N3 C24 C20 123.8(2) . . ?
N3 C24 C16 115.2(2) . . ?
C20 C24 C16 121.0(2) . . ?
C14 C9 C10 118.8(2) . . ?
C14 C9 C8 119.8(2) . . ?
C10 C9 C8 121.4(2) . . ?
C13 C14 C9 120.8(3) . . ?
C12 C13 C14 119.3(3) . . ?
C11 C12 C13 121.3(3) . . ?
C12 C11 C10 120.2(3) . . ?
O5 C10 C11 117.1(2) . . ?
O5 C10 C9 123.3(2) . . ?
C11 C10 C9 119.6(3) . . ?
O4 C16 C17 122.9(2) . . ?
O4 C16 C24 117.4(2) . . ?
C17 C16 C24 119.6(2) . . ?
C16 C17 C18 119.3(2) . . ?
C19 C18 C17 121.7(2) . . ?
C18 C19 C20 120.2(2) . . ?
C24 C20 C21 116.4(2) . . ?
C24 C20 C19 118.1(2) . . ?
C21 C20 C19 125.4(2) . . ?
C22 C21 C20 120.0(2) . . ?
C21 C22 C23 119.2(2) . . ?
N3 C23 C22 122.8(2) . . ?
C7 N1 N2 115.9(2) . . ?
C7 N1 V 129.82(17) . . ?
N2 N1 V 114.26(15) . . ?
C8 N2 N1 110.3(2) . . ?
C23 N3 C24 117.9(2) . . ?
C23 N3 V 134.95(17) . . ?
C24 N3 V 107.19(15) . . ?
C1 O2 V 127.57(16) . . ?
C8 O3 V 117.08(15) . . ?
C16 O4 V 123.70(15) . . ?
O1 V O4 98.55(9) . . ?
O1 V O2 98.55(9) . . ?
O4 V O2 103.16(8) . . ?
O1 V O3 99.44(9) . . ?
O4 V O3 92.73(8) . . ?
O2 V O3 153.88(8) . . ?
O1 V N1 98.68(9) . . ?
O4 V N1 160.61(8) . . ?
O2 V N1 82.98(8) . . ?
O3 V N1 75.71(8) . . ?
O1 V N3 174.75(9) . . ?
O4 V N3 76.21(7) . . ?
O2 V N3 82.59(8) . . ?
O3 V N3 81.23(7) . . ?
N1 V N3 86.54(8) . . ?

_diffrn_measured_fraction_theta_max 0.959
_diffrn_reflns_theta_full        30.00
_diffrn_measured_fraction_theta_full 0.959
_refine_diff_density_max         0.486
_refine_diff_density_min         -0.564
_refine_diff_density_rms         0.092
