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

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_compound5
_database_code_depnum_ccdc_archive 'CCDC 1502023'
_audit_update_record             
;
2016-09-01 deposited with the CCDC.
2016-09-15 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C48 H44 K2 N8 O12 V2'
_chemical_formula_sum            'C48 H44 K2 N8 O12 V2'
_chemical_formula_weight         1104.99

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'
K K 0.2009 0.2494 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
V V 0.3005 0.5294 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   P-1
_symmetry_space_group_name_Hall  -P1

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

_cell_length_a                   8.5326(3)
_cell_length_b                   10.2707(3)
_cell_length_c                   14.0922(5)
_cell_angle_alpha                87.943(2)
_cell_angle_beta                 82.422(2)
_cell_angle_gamma                70.9430(10)
_cell_volume                     1157.07(7)
_cell_formula_units_Z            1
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    31748
_cell_measurement_theta_min      4.723
_cell_measurement_theta_max      52.870

_exptl_crystal_description       Block
_exptl_crystal_colour            orange
_exptl_crystal_size_max          0.41
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.586
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             568
_exptl_absorpt_coefficient_mu    0.659
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7729
_exptl_absorpt_correction_T_max  0.8800
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            38439
_diffrn_reflns_av_R_equivalents  0.0336
_diffrn_reflns_av_unetI/netI     0.0195
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         1.46
_diffrn_reflns_theta_max         26.39
_reflns_number_total             4744
_reflns_number_gt                4288
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Apex2, Bruker Instrument Service v2010, 1-2'
_computing_cell_refinement       
'SAINT V7.68A (Bruker: Madison, 2009 ) in Apex2 suite'
_computing_data_reduction        
'SAINT and XPREP Version 2008/2 (Sheldrick, Bruker AXS Inc.)'
_computing_structure_solution    
'XS V2008/1 (G. M. Sheldrick, Acta Cryst. (2008). A64, 112-122)'
_computing_structure_refinement  
'XL V2008/4 (G. M. Sheldrick, Acta Cryst. (2008). A64, 112-122)'
_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)+(0.0610P)²+0.7085P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4744
_refine_ls_number_parameters     405
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0361
_refine_ls_R_factor_gt           0.0313
_refine_ls_wR_factor_ref         0.1074
_refine_ls_wR_factor_gt          0.0940
_refine_ls_goodness_of_fit_ref   1.132
_refine_ls_restrained_S_all      1.132
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
V1 V 0.43433(4) 0.24158(3) 0.15320(2) 0.01672(11) Uani 1 1 d . . .
K1 K 0.81724(6) 0.18989(5) -0.03773(3) 0.02486(13) Uani 1 1 d . . .
C1 C 0.3950(2) 0.3466(2) 0.34610(14) 0.0184(4) Uani 1 1 d . . .
O1 O 0.29602(19) 0.16245(15) 0.16689(12) 0.0268(3) Uani 1 1 d . . .
O1W O 0.5709(3) 0.1159(2) -0.11758(16) 0.0516(5) Uani 1 1 d . . .
H1WB H 0.5800 0.0175 -0.1322 0.077 Uiso 1 1 d R . .
H1WA H 0.4711 0.1526 -0.0603 0.077 Uiso 1 1 d R . .
N1 N 0.2833(2) 0.45662(16) 0.17078(12) 0.0168(3) Uani 1 1 d . . .
C2 C 0.2674(2) 0.4725(2) 0.33848(14) 0.0180(4) Uani 1 1 d . . .
O2 O 0.61571(19) 0.12869(15) 0.11477(11) 0.0262(3) Uani 1 1 d . . .
O2W O 1.1381(2) 0.09373(17) 0.01345(14) 0.0293(4) Uani 1 1 d . . .
H2WA H 1.179(4) 0.110(3) 0.058(2) 0.036(8) Uiso 1 1 d . . .
H2WB H 1.216(5) 0.056(4) -0.029(3) 0.060(11) Uiso 1 1 d . . .
N2 N 0.2400(2) 0.52534(16) 0.08547(12) 0.0178(3) Uani 1 1 d . . .
N3 N 0.4135(2) 0.32841(17) 0.44006(12) 0.0203(4) Uani 1 1 d . . .
O3 O 0.48648(17) 0.26047(14) 0.27925(10) 0.0198(3) Uani 1 1 d . . .
C3 C 0.2126(2) 0.5214(2) 0.43504(14) 0.0204(4) Uani 1 1 d . . .
N4 N 0.2987(2) 0.43550(18) 0.49587(13) 0.0225(4) Uani 1 1 d . . .
O4 O 0.41795(19) 0.31837(14) 0.02387(10) 0.0242(3) Uani 1 1 d . . .
C4 C 0.0755(3) 0.6485(2) 0.47269(16) 0.0247(4) Uani 1 1 d . . .
H4C H 0.114(3) 0.727(3) 0.464(2) 0.033(7) Uiso 1 1 d . . .
H4B H -0.019(4) 0.665(3) 0.441(2) 0.034(7) Uiso 1 1 d . . .
H4A H 0.038(3) 0.640(3) 0.541(2) 0.036(7) Uiso 1 1 d . . .
C5 C 0.2208(2) 0.53095(19) 0.24958(14) 0.0167(4) Uani 1 1 d . . .
C6 C 0.1090(2) 0.6770(2) 0.24524(14) 0.0176(4) Uani 1 1 d . . .
C7 C 0.1664(3) 0.7841(2) 0.26553(15) 0.0212(4) Uani 1 1 d . . .
H7 H 0.271(3) 0.767(3) 0.2857(18) 0.025(6) Uiso 1 1 d . . .
C8 C 0.0659(3) 0.9203(2) 0.25661(16) 0.0253(4) Uani 1 1 d . . .
H8 H 0.106(3) 0.988(3) 0.269(2) 0.033(7) Uiso 1 1 d . . .
C9 C -0.0937(3) 0.9495(2) 0.23127(16) 0.0267(5) Uani 1 1 d . . .
H9 H -0.160(3) 1.040(3) 0.2255(19) 0.032(7) Uiso 1 1 d . . .
C10 C -0.1530(3) 0.8429(2) 0.21468(15) 0.0248(4) Uani 1 1 d . . .
H10 H -0.267(3) 0.866(3) 0.1983(19) 0.033(7) Uiso 1 1 d . . .
C11 C -0.0515(3) 0.7070(2) 0.21974(14) 0.0205(4) Uani 1 1 d . . .
H11 H -0.090(3) 0.641(3) 0.2067(19) 0.027(7) Uiso 1 1 d . . .
C12 C 0.3118(2) 0.4421(2) 0.01358(14) 0.0185(4) Uani 1 1 d . . .
C13 C 0.2774(2) 0.4890(2) -0.08433(14) 0.0191(4) Uani 1 1 d . . .
C14 C 0.1283(3) 0.5922(2) -0.09901(15) 0.0214(4) Uani 1 1 d . . .
H14 H 0.046(3) 0.627(3) -0.0445(19) 0.026(6) Uiso 1 1 d . . .
C15 C 0.0990(3) 0.6383(2) -0.19107(16) 0.0253(4) Uani 1 1 d . . .
H15 H -0.001(4) 0.708(3) -0.200(2) 0.034(7) Uiso 1 1 d . . .
C16 C 0.2154(3) 0.5793(2) -0.26883(16) 0.0259(5) Uani 1 1 d . . .
H16 H 0.198(3) 0.610(3) -0.333(2) 0.031(7) Uiso 1 1 d . . .
C17 C 0.3614(3) 0.4736(2) -0.25548(15) 0.0247(4) Uani 1 1 d . . .
H17 H 0.445(3) 0.428(3) -0.3133(19) 0.028(6) Uiso 1 1 d . . .
C18 C 0.3926(3) 0.4296(2) -0.16328(15) 0.0219(4) Uani 1 1 d . . .
H18 H 0.500(3) 0.357(3) -0.1542(17) 0.023(6) Uiso 1 1 d . . .
C19 C 0.5214(2) 0.2141(2) 0.48569(15) 0.0202(4) Uani 1 1 d . . .
C20 C 0.6784(3) 0.1426(2) 0.43943(16) 0.0236(4) Uani 1 1 d . . .
H20 H 0.718(3) 0.171(2) 0.3797(18) 0.022(6) Uiso 1 1 d . . .
C21 C 0.7788(3) 0.0275(2) 0.48281(17) 0.0258(5) Uani 1 1 d . . .
H21 H 0.881(3) -0.018(3) 0.449(2) 0.032(7) Uiso 1 1 d . . .
C22 C 0.7233(3) -0.0143(2) 0.57182(17) 0.0272(5) Uani 1 1 d . . .
H22 H 0.790(3) -0.095(3) 0.5980(19) 0.029(6) Uiso 1 1 d . . .
C23 C 0.5689(3) 0.0596(2) 0.61819(16) 0.0272(5) Uani 1 1 d . . .
H23 H 0.535(4) 0.033(3) 0.675(2) 0.038(8) Uiso 1 1 d . . .
C24 C 0.4661(3) 0.1745(2) 0.57537(16) 0.0243(4) Uani 1 1 d . . .
H24 H 0.366(3) 0.224(3) 0.6030(19) 0.027(6) Uiso 1 1 d . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
V1 O1 1.6264(15) . ?
V1 O2 1.6386(15) . ?
V1 O3 1.9185(14) . ?
V1 O4 1.9634(15) . ?
V1 N1 2.1672(16) . ?
V1 K1 3.8532(6) . ?
K1 O2 2.7576(16) . ?
K1 O2W 2.7739(18) . ?
K1 O2W 2.8259(17) 2_755 ?
K1 O1W 2.827(2) . ?
K1 N2 2.8736(17) 2_665 ?
K1 C14 3.188(2) 2_665 ?
K1 C7 3.200(2) 2_665 ?
K1 O4 3.2355(16) . ?
K1 C8 3.239(2) 2_665 ?
K1 C6 3.257(2) 2_665 ?
K1 C9 3.381(2) 2_665 ?
K1 C11 3.396(2) 2_665 ?
C1 O3 1.302(2) . ?
C1 N3 1.353(3) . ?
C1 C2 1.404(3) . ?
O1W H1WB 1.0145 . ?
O1W H1WA 1.0719 . ?
N1 C5 1.319(3) . ?
N1 N2 1.402(2) . ?
C2 C5 1.417(3) . ?
C2 C3 1.432(3) . ?
O2W K1 2.8259(17) 2_755 ?
O2W H2WA 0.80(3) . ?
O2W H2WB 0.84(4) . ?
N2 C12 1.299(3) . ?
N2 K1 2.8736(17) 2_665 ?
N3 N4 1.394(2) . ?
N3 C19 1.427(3) . ?
C3 N4 1.320(3) . ?
C3 C4 1.497(3) . ?
O4 C12 1.314(2) . ?
C4 H4C 0.96(3) . ?
C4 H4B 0.93(3) . ?
C4 H4A 0.98(3) . ?
C5 C6 1.497(3) . ?
C6 C7 1.393(3) . ?
C6 C11 1.395(3) . ?
C6 K1 3.257(2) 2_665 ?
C7 C8 1.393(3) . ?
C7 K1 3.200(2) 2_665 ?
C7 H7 0.93(3) . ?
C8 C9 1.388(3) . ?
C8 K1 3.239(2) 2_665 ?
C8 H8 0.90(3) . ?
C9 C10 1.385(3) . ?
C9 K1 3.381(2) 2_665 ?
C9 H9 0.93(3) . ?
C10 C11 1.386(3) . ?
C10 K1 3.476(2) 2_665 ?
C10 H10 0.98(3) . ?
C11 K1 3.396(2) 2_665 ?
C11 H11 0.88(3) . ?
C12 C13 1.480(3) . ?
C13 C18 1.395(3) . ?
C13 C14 1.399(3) . ?
C14 C15 1.391(3) . ?
C14 K1 3.188(2) 2_665 ?
C14 H14 0.96(3) . ?
C15 C16 1.386(3) . ?
C15 H15 0.94(3) . ?
C16 C17 1.390(3) . ?
C16 H16 0.97(3) . ?
C17 C18 1.391(3) . ?
C17 H17 1.02(3) . ?
C18 H18 0.99(3) . ?
C19 C24 1.384(3) . ?
C19 C20 1.385(3) . ?
C20 C21 1.389(3) . ?
C20 H20 0.94(3) . ?
C21 C22 1.386(3) . ?
C21 H21 0.92(3) . ?
C22 C23 1.376(3) . ?
C22 H22 0.93(3) . ?
C23 C24 1.393(3) . ?
C23 H23 0.88(3) . ?
C24 H24 0.88(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 V1 O2 107.95(8) . . ?
O1 V1 O3 105.78(7) . . ?
O2 V1 O3 95.76(7) . . ?
O1 V1 O4 103.69(7) . . ?
O2 V1 O4 89.89(7) . . ?
O3 V1 O4 146.55(6) . . ?
O1 V1 N1 103.09(7) . . ?
O2 V1 N1 147.53(7) . . ?
O3 V1 N1 84.62(6) . . ?
O4 V1 N1 73.54(6) . . ?
O1 V1 K1 130.01(6) . . ?
O2 V1 K1 38.17(5) . . ?
O3 V1 K1 111.79(4) . . ?
O4 V1 K1 57.03(4) . . ?
N1 V1 K1 111.97(4) . . ?
O2 K1 O2W 105.35(5) . . ?
O2 K1 O2W 65.22(5) . 2_755 ?
O2W K1 O2W 78.87(5) . 2_755 ?
O2 K1 O1W 73.92(6) . . ?
O2W K1 O1W 144.74(6) . . ?
O2W K1 O1W 68.79(6) 2_755 . ?
O2 K1 N2 118.09(5) . 2_665 ?
O2W K1 N2 105.49(5) . 2_665 ?
O2W K1 N2 172.83(5) 2_755 2_665 ?
O1W K1 N2 105.47(6) . 2_665 ?
O2 K1 C14 87.35(5) . 2_665 ?
O2W K1 C14 69.95(5) . 2_665 ?
O2W K1 C14 130.94(6) 2_755 2_665 ?
O1W K1 C14 143.49(6) . 2_665 ?
N2 K1 C14 56.23(5) 2_665 2_665 ?
O2 K1 C7 138.66(5) . 2_665 ?
O2W K1 C7 109.94(6) . 2_665 ?
O2W K1 C7 101.09(6) 2_755 2_665 ?
O1W K1 C7 64.86(6) . 2_665 ?
N2 K1 C7 72.18(5) 2_665 2_665 ?
C14 K1 C7 124.51(5) 2_665 2_665 ?
O2 K1 O4 49.68(4) . . ?
O2W K1 O4 149.50(5) . . ?
O2W K1 O4 100.24(5) 2_755 . ?
O1W K1 O4 54.51(5) . . ?
N2 K1 O4 78.95(4) 2_665 . ?
C14 K1 O4 89.44(5) 2_665 . ?
C7 K1 O4 100.20(5) 2_665 . ?
O2 K1 C8 134.29(6) . 2_665 ?
O2W K1 C8 94.14(6) . 2_665 ?
O2W K1 C8 79.10(6) 2_755 2_665 ?
O1W K1 C8 66.85(6) . 2_665 ?
N2 K1 C8 94.78(5) 2_665 2_665 ?
C14 K1 C8 138.36(6) 2_665 2_665 ?
C7 K1 C8 24.98(5) 2_665 2_665 ?
O4 K1 C8 115.80(5) . 2_665 ?
O2 K1 C6 154.56(5) . 2_665 ?
O2W K1 C6 100.03(5) . 2_665 ?
O2W K1 C6 122.66(5) 2_755 2_665 ?
O1W K1 C6 86.42(6) . 2_665 ?
N2 K1 C6 51.44(5) 2_665 2_665 ?
C14 K1 C6 99.84(5) 2_665 2_665 ?
C7 K1 C6 24.91(5) 2_665 2_665 ?
O4 K1 C6 105.63(4) . 2_665 ?
C8 K1 C6 43.59(5) 2_665 2_665 ?
O2 K1 C9 143.15(5) . 2_665 ?
O2W K1 C9 70.29(6) . 2_665 ?
O2W K1 C9 78.22(6) 2_755 2_665 ?
O1W K1 C9 89.20(6) . 2_665 ?
N2 K1 C9 97.74(5) 2_665 2_665 ?
C14 K1 C9 122.19(6) 2_665 2_665 ?
C7 K1 C9 42.84(5) 2_665 2_665 ?
O4 K1 C9 139.86(5) . 2_665 ?
C8 K1 C9 24.07(6) 2_665 2_665 ?
C6 K1 C9 49.55(5) 2_665 2_665 ?
O2 K1 C11 175.26(5) . 2_665 ?
O2W K1 C11 76.11(5) . 2_665 ?
O2W K1 C11 119.51(5) 2_755 2_665 ?
O1W K1 C11 107.60(6) . 2_665 ?
N2 K1 C11 57.25(5) 2_665 2_665 ?
C14 K1 C11 88.96(5) 2_665 2_665 ?
C7 K1 C11 42.75(5) 2_665 2_665 ?
O4 K1 C11 127.34(4) . 2_665 ?
C8 K1 C11 49.46(6) 2_665 2_665 ?
C6 K1 C11 24.09(5) 2_665 2_665 ?
C9 K1 C11 41.58(5) 2_665 2_665 ?
O3 C1 N3 123.48(18) . . ?
O3 C1 C2 129.59(18) . . ?
N3 C1 C2 106.91(17) . . ?
K1 O1W H1WB 124.0 . . ?
K1 O1W H1WA 97.8 . . ?
H1WB O1W H1WA 107.3 . . ?
C5 N1 N2 115.25(15) . . ?
C5 N1 V1 129.85(13) . . ?
N2 N1 V1 114.85(11) . . ?
C1 C2 C5 123.12(18) . . ?
C1 C2 C3 104.66(17) . . ?
C5 C2 C3 132.14(18) . . ?
V1 O2 K1 120.29(7) . . ?
K1 O2W K1 101.13(5) . 2_755 ?
K1 O2W H2WA 133(2) . . ?
K1 O2W H2WA 102(2) 2_755 . ?
K1 O2W H2WB 117(2) . . ?
K1 O2W H2WB 77(2) 2_755 . ?
H2WA O2W H2WB 107(3) . . ?
C12 N2 N1 109.10(16) . . ?
C12 N2 K1 113.19(12) . 2_665 ?
N1 N2 K1 129.36(11) . 2_665 ?
C1 N3 N4 111.46(16) . . ?
C1 N3 C19 128.93(17) . . ?
N4 N3 C19 119.42(16) . . ?
C1 O3 V1 127.28(13) . . ?
N4 C3 C2 111.30(18) . . ?
N4 C3 C4 119.18(19) . . ?
C2 C3 C4 129.50(18) . . ?
C3 N4 N3 105.63(16) . . ?
C12 O4 V1 118.61(13) . . ?
C12 O4 K1 131.67(12) . . ?
V1 O4 K1 92.36(5) . . ?
C3 C4 H4C 109.8(16) . . ?
C3 C4 H4B 111.5(17) . . ?
H4C C4 H4B 109(2) . . ?
C3 C4 H4A 111.6(16) . . ?
H4C C4 H4A 109(2) . . ?
H4B C4 H4A 106(2) . . ?
N1 C5 C2 118.97(17) . . ?
N1 C5 C6 120.78(17) . . ?
C2 C5 C6 120.19(17) . . ?
C7 C6 C11 119.70(18) . . ?
C7 C6 C5 119.76(18) . . ?
C11 C6 C5 120.53(18) . . ?
C7 C6 K1 75.28(12) . 2_665 ?
C11 C6 K1 83.55(12) . 2_665 ?
C5 C6 K1 110.58(12) . 2_665 ?
C8 C7 C6 119.9(2) . . ?
C8 C7 K1 79.08(13) . 2_665 ?
C6 C7 K1 79.81(12) . 2_665 ?
C8 C7 H7 118.8(16) . . ?
C6 C7 H7 121.3(16) . . ?
K1 C7 H7 111.9(16) 2_665 . ?
C9 C8 C7 120.1(2) . . ?
C9 C8 K1 83.70(13) . 2_665 ?
C7 C8 K1 75.94(12) . 2_665 ?
C9 C8 H8 121.4(18) . . ?
C7 C8 H8 118.5(18) . . ?
K1 C8 H8 112.1(18) 2_665 . ?
C10 C9 C8 119.9(2) . . ?
C10 C9 K1 82.23(13) . 2_665 ?
C8 C9 K1 72.23(12) . 2_665 ?
C10 C9 H9 120.4(17) . . ?
C8 C9 H9 119.7(17) . . ?
K1 C9 H9 116.0(17) 2_665 . ?
C9 C10 C11 120.4(2) . . ?
C9 C10 K1 74.51(13) . 2_665 ?
C11 C10 K1 75.12(12) . 2_665 ?
C9 C10 H10 118.6(16) . . ?
C11 C10 H10 121.0(16) . . ?
K1 C10 H10 120.9(16) 2_665 . ?
C10 C11 C6 119.9(2) . . ?
C10 C11 K1 81.64(13) . 2_665 ?
C6 C11 K1 72.36(11) . 2_665 ?
C10 C11 H11 118.8(17) . . ?
C6 C11 H11 121.2(17) . . ?
K1 C11 H11 116.8(17) 2_665 . ?
N2 C12 O4 122.60(18) . . ?
N2 C12 C13 119.18(17) . . ?
O4 C12 C13 118.20(17) . . ?
C18 C13 C14 119.19(19) . . ?
C18 C13 C12 120.29(18) . . ?
C14 C13 C12 120.52(18) . . ?
C15 C14 C13 120.1(2) . . ?
C15 C14 K1 115.11(14) . 2_665 ?
C13 C14 K1 94.29(12) . 2_665 ?
C15 C14 H14 121.4(15) . . ?
C13 C14 H14 118.5(15) . . ?
K1 C14 H14 61.9(15) 2_665 . ?
C16 C15 C14 120.1(2) . . ?
C16 C15 H15 120.2(17) . . ?
C14 C15 H15 119.7(17) . . ?
C15 C16 C17 120.4(2) . . ?
C15 C16 H16 121.2(16) . . ?
C17 C16 H16 118.4(16) . . ?
C16 C17 C18 119.6(2) . . ?
C16 C17 H17 120.1(15) . . ?
C18 C17 H17 120.3(15) . . ?
C17 C18 C13 120.59(19) . . ?
C17 C18 H18 119.1(14) . . ?
C13 C18 H18 120.3(14) . . ?
C24 C19 C20 120.83(19) . . ?
C24 C19 N3 119.22(19) . . ?
C20 C19 N3 119.95(19) . . ?
C19 C20 C21 119.2(2) . . ?
C19 C20 H20 121.3(15) . . ?
C21 C20 H20 119.5(15) . . ?
C22 C21 C20 120.3(2) . . ?
C22 C21 H21 123.0(17) . . ?
C20 C21 H21 116.7(17) . . ?
C23 C22 C21 119.9(2) . . ?
C23 C22 H22 121.0(16) . . ?
C21 C22 H22 119.1(16) . . ?
C22 C23 C24 120.5(2) . . ?
C22 C23 H23 119.5(19) . . ?
C24 C23 H23 120.0(19) . . ?
C19 C24 C23 119.2(2) . . ?
C19 C24 H24 118.2(17) . . ?
C23 C24 H24 122.7(17) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 V1 N1 C5 84.00(17) . . . . ?
O2 V1 N1 C5 -113.27(19) . . . . ?
O3 V1 N1 C5 -20.99(17) . . . . ?
O4 V1 N1 C5 -175.36(18) . . . . ?
K1 V1 N1 C5 -132.33(16) . . . . ?
O1 V1 N1 N2 -93.10(13) . . . . ?
O2 V1 N1 N2 69.63(18) . . . . ?
O3 V1 N1 N2 161.91(13) . . . . ?
O4 V1 N1 N2 7.54(12) . . . . ?
K1 V1 N1 N2 50.57(13) . . . . ?
O3 C1 C2 C5 -2.8(3) . . . . ?
N3 C1 C2 C5 175.41(18) . . . . ?
O3 C1 C2 C3 -179.8(2) . . . . ?
N3 C1 C2 C3 -1.6(2) . . . . ?
O1 V1 O2 K1 132.96(9) . . . . ?
O3 V1 O2 K1 -118.38(8) . . . . ?
O4 V1 O2 K1 28.59(8) . . . . ?
N1 V1 O2 K1 -29.35(17) . . . . ?
O2W K1 O2 V1 137.50(9) . . . . ?
O2W K1 O2 V1 -152.81(10) 2_755 . . . ?
O1W K1 O2 V1 -79.17(9) . . . . ?
N2 K1 O2 V1 20.08(11) 2_665 . . . ?
C14 K1 O2 V1 69.13(9) 2_665 . . . ?
C7 K1 O2 V1 -74.58(12) 2_665 . . . ?
O4 K1 O2 V1 -22.39(7) . . . . ?
C8 K1 O2 V1 -110.65(10) 2_665 . . . ?
C6 K1 O2 V1 -38.40(17) 2_665 . . . ?
C9 K1 O2 V1 -145.04(9) 2_665 . . . ?
C11 K1 O2 V1 30.2(6) 2_665 . . . ?
O2 K1 O2W K1 60.21(6) . . . 2_755 ?
O2W K1 O2W K1 0.0 2_755 . . 2_755 ?
O1W K1 O2W K1 -23.52(13) . . . 2_755 ?
N2 K1 O2W K1 -174.15(5) 2_665 . . 2_755 ?
C14 K1 O2W K1 141.51(7) 2_665 . . 2_755 ?
C7 K1 O2W K1 -97.88(6) 2_665 . . 2_755 ?
O4 K1 O2W K1 91.32(10) . . . 2_755 ?
C8 K1 O2W K1 -78.03(6) 2_665 . . 2_755 ?
C6 K1 O2W K1 -121.58(6) 2_665 . . 2_755 ?
C9 K1 O2W K1 -81.34(6) 2_665 . . 2_755 ?
C11 K1 O2W K1 -124.46(7) 2_665 . . 2_755 ?
C5 N1 N2 C12 178.71(17) . . . . ?
V1 N1 N2 C12 -3.75(19) . . . . ?
C5 N1 N2 K1 33.3(2) . . . 2_665 ?
V1 N1 N2 K1 -149.15(8) . . . 2_665 ?
O3 C1 N3 N4 -179.59(17) . . . . ?
C2 C1 N3 N4 2.1(2) . . . . ?
O3 C1 N3 C19 -4.7(3) . . . . ?
C2 C1 N3 C19 176.94(19) . . . . ?
N3 C1 O3 V1 159.46(15) . . . . ?
C2 C1 O3 V1 -22.6(3) . . . . ?
O1 V1 O3 C1 -75.31(17) . . . . ?
O2 V1 O3 C1 174.18(16) . . . . ?
O4 V1 O3 C1 75.6(2) . . . . ?
N1 V1 O3 C1 26.80(16) . . . . ?
K1 V1 O3 C1 138.34(15) . . . . ?
C1 C2 C3 N4 0.6(2) . . . . ?
C5 C2 C3 N4 -176.0(2) . . . . ?
C1 C2 C3 C4 -177.8(2) . . . . ?
C5 C2 C3 C4 5.6(4) . . . . ?
C2 C3 N4 N3 0.6(2) . . . . ?
C4 C3 N4 N3 179.15(18) . . . . ?
C1 N3 N4 C3 -1.7(2) . . . . ?
C19 N3 N4 C3 -177.09(18) . . . . ?
O1 V1 O4 C12 89.59(15) . . . . ?
O2 V1 O4 C12 -161.94(15) . . . . ?
O3 V1 O4 C12 -61.63(19) . . . . ?
N1 V1 O4 C12 -10.26(14) . . . . ?
K1 V1 O4 C12 -141.30(16) . . . . ?
O1 V1 O4 K1 -129.10(6) . . . . ?
O2 V1 O4 K1 -20.64(6) . . . . ?
O3 V1 O4 K1 79.68(11) . . . . ?
N1 V1 O4 K1 131.04(6) . . . . ?
O2 K1 O4 C12 148.65(18) . . . . ?
O2W K1 O4 C12 107.84(17) . . . . ?
O2W K1 O4 C12 -166.73(16) 2_755 . . . ?
O1W K1 O4 C12 -112.20(17) . . . . ?
N2 K1 O4 C12 6.02(16) 2_665 . . . ?
C14 K1 O4 C12 61.65(16) 2_665 . . . ?
C7 K1 O4 C12 -63.38(16) 2_665 . . . ?
C8 K1 O4 C12 -83.98(17) 2_665 . . . ?
C6 K1 O4 C12 -38.42(17) 2_665 . . . ?
C9 K1 O4 C12 -82.91(18) 2_665 . . . ?
C11 K1 O4 C12 -26.61(18) 2_665 . . . ?
O2 K1 O4 V1 15.94(5) . . . . ?
O2W K1 O4 V1 -24.87(11) . . . . ?
O2W K1 O4 V1 60.56(6) 2_755 . . . ?
O1W K1 O4 V1 115.09(8) . . . . ?
N2 K1 O4 V1 -126.69(6) 2_665 . . . ?
C14 K1 O4 V1 -71.06(6) 2_665 . . . ?
C7 K1 O4 V1 163.92(6) 2_665 . . . ?
C8 K1 O4 V1 143.32(6) 2_665 . . . ?
C6 K1 O4 V1 -171.12(5) 2_665 . . . ?
C9 K1 O4 V1 144.38(7) 2_665 . . . ?
C11 K1 O4 V1 -159.32(6) 2_665 . . . ?
N2 N1 C5 C2 -175.77(16) . . . . ?
V1 N1 C5 C2 7.1(3) . . . . ?
N2 N1 C5 C6 1.3(3) . . . . ?
V1 N1 C5 C6 -175.75(13) . . . . ?
C1 C2 C5 N1 9.4(3) . . . . ?
C3 C2 C5 N1 -174.5(2) . . . . ?
C1 C2 C5 C6 -167.71(18) . . . . ?
C3 C2 C5 C6 8.4(3) . . . . ?
N1 C5 C6 C7 -109.8(2) . . . . ?
C2 C5 C6 C7 67.3(3) . . . . ?
N1 C5 C6 C11 69.3(3) . . . . ?
C2 C5 C6 C11 -113.6(2) . . . . ?
N1 C5 C6 K1 -25.4(2) . . . 2_665 ?
C2 C5 C6 K1 151.70(14) . . . 2_665 ?
C11 C6 C7 C8 -2.5(3) . . . . ?
C5 C6 C7 C8 176.59(19) . . . . ?
K1 C6 C7 C8 71.02(19) 2_665 . . . ?
C11 C6 C7 K1 -73.53(17) . . . 2_665 ?
C5 C6 C7 K1 105.57(17) . . . 2_665 ?
C6 C7 C8 C9 2.6(3) . . . . ?
K1 C7 C8 C9 74.0(2) 2_665 . . . ?
C6 C7 C8 K1 -71.42(18) . . . 2_665 ?
C7 C8 C9 C10 -0.1(3) . . . . ?
K1 C8 C9 C10 69.6(2) 2_665 . . . ?
C7 C8 C9 K1 -69.73(19) . . . 2_665 ?
C8 C9 C10 C11 -2.4(3) . . . . ?
K1 C9 C10 C11 61.87(19) 2_665 . . . ?
C8 C9 C10 K1 -64.29(19) . . . 2_665 ?
C9 C10 C11 C6 2.5(3) . . . . ?
K1 C10 C11 C6 64.02(17) 2_665 . . . ?
C9 C10 C11 K1 -61.57(19) . . . 2_665 ?
C7 C6 C11 C10 0.0(3) . . . . ?
C5 C6 C11 C10 -179.08(18) . . . . ?
K1 C6 C11 C10 -68.95(18) 2_665 . . . ?
C7 C6 C11 K1 68.97(17) . . . 2_665 ?
C5 C6 C11 K1 -110.13(17) . . . 2_665 ?
N1 N2 C12 O4 -5.2(3) . . . . ?
K1 N2 C12 O4 146.30(15) 2_665 . . . ?
N1 N2 C12 C13 176.65(16) . . . . ?
K1 N2 C12 C13 -31.9(2) 2_665 . . . ?
V1 O4 C12 N2 12.8(3) . . . . ?
K1 O4 C12 N2 -110.42(19) . . . . ?
V1 O4 C12 C13 -168.98(13) . . . . ?
K1 O4 C12 C13 67.8(2) . . . . ?
N2 C12 C13 C18 155.57(19) . . . . ?
O4 C12 C13 C18 -22.7(3) . . . . ?
N2 C12 C13 C14 -25.2(3) . . . . ?
O4 C12 C13 C14 156.56(19) . . . . ?
C18 C13 C14 C15 -2.5(3) . . . . ?
C12 C13 C14 C15 178.21(18) . . . . ?
C18 C13 C14 K1 -124.91(17) . . . 2_665 ?
C12 C13 C14 K1 55.84(18) . . . 2_665 ?
C13 C14 C15 C16 1.9(3) . . . . ?
K1 C14 C15 C16 113.43(19) 2_665 . . . ?
C14 C15 C16 C17 0.3(3) . . . . ?
C15 C16 C17 C18 -1.8(3) . . . . ?
C16 C17 C18 C13 1.1(3) . . . . ?
C14 C13 C18 C17 1.0(3) . . . . ?
C12 C13 C18 C17 -179.71(19) . . . . ?
C1 N3 C19 C24 -143.6(2) . . . . ?
N4 N3 C19 C24 30.9(3) . . . . ?
C1 N3 C19 C20 35.2(3) . . . . ?
N4 N3 C19 C20 -150.29(19) . . . . ?
C24 C19 C20 C21 1.9(3) . . . . ?
N3 C19 C20 C21 -176.91(19) . . . . ?
C19 C20 C21 C22 -0.7(3) . . . . ?
C20 C21 C22 C23 -1.0(3) . . . . ?
C21 C22 C23 C24 1.5(3) . . . . ?
C20 C19 C24 C23 -1.3(3) . . . . ?
N3 C19 C24 C23 177.49(19) . . . . ?
C22 C23 C24 C19 -0.4(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
O1W H1WB O1 1.01 1.85 2.785(3) 151.7 2_655
O1W H1WB O2 1.01 2.57 3.381(3) 136.8 2_655
O1W H1WA O4 1.07 2.00 2.800(2) 128.6 .
O2W H2WA O1 0.80(3) 2.11(3) 2.914(2) 176(3) 1_655
O2W H2WB O2 0.84(4) 2.24(4) 3.010(2) 152(3) 2_755

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        26.39
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.425
_refine_diff_density_min         -0.654
_refine_diff_density_rms         0.100
####################################################################### 
# 
# 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_Compound6
_database_code_depnum_ccdc_archive 'CCDC 1502024'
_audit_update_record             
;
2016-09-01 deposited with the CCDC.
2016-09-15 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C44 H38 K2 N8 O14 V2'
_chemical_formula_sum            'C44 H38 K2 N8 O14 V2'
_chemical_formula_weight         1082.90

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'
K K 0.2009 0.2494 '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
_symmetry_space_group_name_Hall  -P2ybc

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                   11.6725(8)
_cell_length_b                   22.2312(15)
_cell_length_c                   9.1846(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 96.914(2)
_cell_angle_gamma                90.00
_cell_volume                     2366.0(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    36822
_cell_measurement_theta_min      5.078
_cell_measurement_theta_max      49.620

_exptl_crystal_description       block
_exptl_crystal_colour            orange
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.520
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1108
_exptl_absorpt_coefficient_mu    0.646
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8298
_exptl_absorpt_correction_T_max  0.9382
_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  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            35394
_diffrn_reflns_av_R_equivalents  0.0515
_diffrn_reflns_av_unetI/netI     0.0507
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_k_max       29
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         1.76
_diffrn_reflns_theta_max         28.62
_reflns_number_total             5901
_reflns_number_gt                3365
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Apex2, Bruker Instrument Service v2010, 1-2'
_computing_cell_refinement       
'SAINT V7.68A (Bruker: Madison, 2009 ) in Apex2 suite'
_computing_data_reduction        
'SAINT and XPREP Version 2008/2 (Sheldrick, Bruker AXS Inc.)'
_computing_structure_solution    
'XS V2008/1 (G. M. Sheldrick, Acta Cryst. (2008). A64, 112-122)'
_computing_structure_refinement  
'XL V2008/4 (G. M. Sheldrick, Acta Cryst. (2008). A64, 112-122)'
_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)+(0.1155P)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    mixed
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0190(19)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         5901
_refine_ls_number_parameters     328
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1190
_refine_ls_R_factor_gt           0.0603
_refine_ls_wR_factor_ref         0.1986
_refine_ls_wR_factor_gt          0.1564
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_restrained_S_all      1.033
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
V1 V 0.63248(4) 0.10420(2) 0.41623(6) 0.0403(2) Uani 1 1 d . . .
O1 O 0.7249(2) 0.13091(12) 0.3176(3) 0.0567(7) Uani 1 1 d . . .
O1W O 0.4481(4) 0.16818(17) 0.0414(4) 0.1220(14) Uani 1 1 d . . .
H1WA H 0.4692 0.1431 0.1093 0.146 Uiso 1 1 d R . .
H1WB H 0.3871 0.1853 0.0624 0.146 Uiso 1 1 d R . .
K1 K 0.50318(8) -0.14782(4) 0.24739(10) 0.0643(3) Uani 1 1 d . . .
N1 N 0.6499(2) 0.00623(12) 0.4056(3) 0.0390(6) Uani 1 1 d . . .
C1 C 0.8019(3) 0.05642(14) 0.6354(3) 0.0382(7) Uani 1 1 d . A .
O2 O 0.55794(19) 0.16059(10) 0.4707(3) 0.0529(6) Uani 1 1 d . . .
O2WA O 0.4048(7) -0.2561(3) 0.2743(12) 0.165(5) Uani 0.594(13) 1 d P A 1
H2WA H 0.3230 -0.2582 0.2602 0.247 Uiso 0.594(13) 1 d PR A 1
O2WB O 0.6476(12) 0.2264(5) 0.926(4) 0.31(2) Uani 0.406(13) 1 d P . 2
H2WB H 0.6814 0.2308 1.0216 0.459 Uiso 0.406(13) 1 d PR A 2
N2 N 0.5652(2) -0.02263(12) 0.3089(3) 0.0412(6) Uani 1 1 d . A .
C2 C 0.8160(2) -0.00082(14) 0.5783(3) 0.0380(7) Uani 1 1 d . . .
N3 N 0.8959(2) 0.06712(12) 0.7342(3) 0.0425(6) Uani 1 1 d . . .
O3 O 0.71748(18) 0.09429(10) 0.6092(2) 0.0439(5) Uani 1 1 d . . .
C3 C 0.9234(2) -0.02253(15) 0.6523(3) 0.0410(7) Uani 1 1 d . A .
N4 N 0.9708(2) 0.01838(13) 0.7457(3) 0.0459(7) Uani 1 1 d . A .
O4 O 0.50288(18) 0.07525(10) 0.2769(3) 0.0486(6) Uani 1 1 d . . .
C4 C 0.9866(3) -0.07904(16) 0.6320(4) 0.0504(8) Uani 1 1 d . . .
H4C H 0.9973 -0.0834 0.5305 0.076 Uiso 1 1 calc R A .
H4B H 0.9431 -0.1125 0.6619 0.076 Uiso 1 1 calc R . .
H4A H 1.0605 -0.0778 0.6905 0.076 Uiso 1 1 calc R . .
O5 O 0.39532(19) -0.05725(10) 0.0886(3) 0.0495(6) Uani 1 1 d . A .
C5 C 0.7321(2) -0.02800(14) 0.4711(3) 0.0366(7) Uani 1 1 d . A .
C6 C 0.7393(2) -0.09359(13) 0.4384(3) 0.0377(7) Uani 1 1 d . A .
C7 C 0.7837(3) -0.11286(15) 0.3131(4) 0.0493(8) Uani 1 1 d . A .
H7 H 0.8090 -0.0850 0.2485 0.059 Uiso 1 1 calc R . .
C8 C 0.7901(3) -0.17414(17) 0.2844(4) 0.0571(9) Uani 1 1 d . . .
H8 H 0.8209 -0.1873 0.2012 0.069 Uiso 1 1 calc R A .
C9 C 0.7511(3) -0.21535(17) 0.3784(5) 0.0582(10) Uani 1 1 d . A .
H9 H 0.7534 -0.2562 0.3573 0.070 Uiso 1 1 calc R . .
C10 C 0.7086(3) -0.19621(16) 0.5041(4) 0.0566(10) Uani 1 1 d . A .
H10 H 0.6830 -0.2242 0.5680 0.068 Uiso 1 1 calc R . .
C11 C 0.7038(3) -0.13527(15) 0.5355(4) 0.0453(8) Uani 1 1 d . A .
H11 H 0.6768 -0.1225 0.6216 0.054 Uiso 1 1 calc R . .
C12 C 0.9242(3) 0.12117(16) 0.8168(4) 0.0468(8) Uani 1 1 d . A .
C13 C 0.8881(3) 0.17625(17) 0.7601(4) 0.0588(10) Uani 1 1 d . . .
H13 H 0.8452 0.1786 0.6682 0.071 Uiso 1 1 calc R A .
C14 C 0.9156(4) 0.22811(19) 0.8399(5) 0.0730(12) Uani 1 1 d . A .
H14 H 0.8894 0.2653 0.8031 0.088 Uiso 1 1 calc R . .
C15 C 0.9815(4) 0.2244(2) 0.9732(5) 0.0765(13) Uani 1 1 d . . .
H15 H 1.0008 0.2592 1.0266 0.092 Uiso 1 1 calc R A .
C16 C 1.0194(4) 0.1699(2) 1.0288(4) 0.0750(13) Uani 1 1 d . A .
H16 H 1.0647 0.1681 1.1192 0.090 Uiso 1 1 calc R . .
C17 C 0.9909(3) 0.11705(18) 0.9513(4) 0.0608(10) Uani 1 1 d . . .
H17 H 1.0160 0.0799 0.9892 0.073 Uiso 1 1 calc R A .
C18 C 0.4954(2) 0.01803(14) 0.2463(3) 0.0389(7) Uani 1 1 d . A .
C19 C 0.3994(3) 0.00104(14) 0.1382(3) 0.0405(7) Uani 1 1 d . . .
C20 C 0.3069(3) 0.03101(17) 0.0737(4) 0.0550(9) Uani 1 1 d . A .
H20 H 0.2893 0.0712 0.0883 0.066 Uiso 1 1 calc R . .
C21 C 0.2413(3) -0.00991(18) -0.0205(4) 0.0564(9) Uani 1 1 d . . .
H21 H 0.1724 -0.0018 -0.0791 0.068 Uiso 1 1 calc R A .
C22 C 0.2963(3) -0.06159(18) -0.0091(4) 0.0549(9) Uani 1 1 d . A .
H22 H 0.2718 -0.0963 -0.0600 0.066 Uiso 1 1 calc R . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
V1 O1 1.604(2) . ?
V1 O2 1.638(2) . ?
V1 O3 1.937(2) . ?
V1 O4 1.968(2) . ?
V1 N1 2.191(3) . ?
V1 K1 3.7644(11) 3_656 ?
O1W K1 2.815(4) 3_655 ?
O1W H1WA 0.8503 . ?
O1W H1WB 0.8500 . ?
K1 O2WA 2.691(8) . ?
K1 O5 2.707(2) . ?
K1 O2 2.782(3) 3_656 ?
K1 O1W 2.815(4) 3_655 ?
K1 O2WB 2.83(2) 3_656 ?
K1 N2 2.914(3) . ?
K1 O3 3.256(2) 3_656 ?
K1 C6 3.311(3) . ?
K1 C11 3.328(3) . ?
K1 C10 3.332(4) . ?
K1 C7 3.348(3) . ?
K1 C9 3.352(4) . ?
N1 C5 1.313(4) . ?
N1 N2 1.403(3) . ?
C1 O3 1.297(4) . ?
C1 N3 1.358(4) . ?
C1 C2 1.393(4) . ?
O2 K1 2.782(3) 3_656 ?
O2WA H2WA 0.9501 . ?
O2WB K1 2.83(2) 3_656 ?
O2WB H2WB 0.9200 . ?
N2 C18 1.303(4) . ?
C2 C5 1.435(4) . ?
C2 C3 1.436(4) . ?
N3 N4 1.389(4) . ?
N3 C12 1.438(4) . ?
O3 K1 3.256(2) 3_656 ?
C3 N4 1.325(4) . ?
C3 C4 1.480(5) . ?
O4 C18 1.303(4) . ?
C4 H4C 0.9600 . ?
C4 H4B 0.9600 . ?
C4 H4A 0.9600 . ?
O5 C19 1.373(4) . ?
O5 C22 1.378(4) . ?
C5 C6 1.493(4) . ?
C6 C11 1.384(4) . ?
C6 C7 1.385(5) . ?
C7 C8 1.391(5) . ?
C7 H7 0.9300 . ?
C8 C9 1.374(5) . ?
C8 H8 0.9300 . ?
C9 C10 1.377(5) . ?
C9 H9 0.9300 . ?
C10 C11 1.388(5) . ?
C10 H10 0.9300 . ?
C11 H11 0.9300 . ?
C12 C13 1.377(5) . ?
C12 C17 1.382(5) . ?
C13 C14 1.383(5) . ?
C13 H13 0.9300 . ?
C14 C15 1.369(6) . ?
C14 H14 0.9300 . ?
C15 C16 1.367(6) . ?
C15 H15 0.9300 . ?
C16 C17 1.393(5) . ?
C16 H16 0.9300 . ?
C17 H17 0.9300 . ?
C18 C19 1.454(4) . ?
C19 C20 1.344(4) . ?
C20 C21 1.415(5) . ?
C20 H20 0.9300 . ?
C21 C22 1.314(5) . ?
C21 H21 0.9300 . ?
C22 H22 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 V1 O2 107.90(13) . . ?
O1 V1 O3 104.69(11) . . ?
O2 V1 O3 92.30(11) . . ?
O1 V1 O4 105.69(12) . . ?
O2 V1 O4 93.09(10) . . ?
O3 V1 O4 145.76(10) . . ?
O1 V1 N1 105.68(12) . . ?
O2 V1 N1 146.11(12) . . ?
O3 V1 N1 83.55(9) . . ?
O4 V1 N1 73.39(9) . . ?
O1 V1 K1 138.26(9) . 3_656 ?
O2 V1 K1 42.35(9) . 3_656 ?
O3 V1 K1 59.87(7) . 3_656 ?
O4 V1 K1 104.57(7) . 3_656 ?
N1 V1 K1 110.08(7) . 3_656 ?
K1 O1W H1WA 120.8 3_655 . ?
K1 O1W H1WB 123.8 3_655 . ?
H1WA O1W H1WB 107.7 . . ?
O2WA K1 O5 122.62(19) . . ?
O2WA K1 O2 70.3(2) . 3_656 ?
O5 K1 O2 115.01(7) . 3_656 ?
O2WA K1 O1W 94.6(3) . 3_655 ?
O5 K1 O1W 75.25(9) . 3_655 ?
O2 K1 O1W 164.59(10) 3_656 3_655 ?
O2WA K1 O2WB 42.0(6) . 3_656 ?
O5 K1 O2WB 86.4(6) . 3_656 ?
O2 K1 O2WB 104.5(6) 3_656 3_656 ?
O1W K1 O2WB 63.4(5) 3_655 3_656 ?
O2WA K1 N2 159.3(2) . . ?
O5 K1 N2 58.83(7) . . ?
O2 K1 N2 90.15(8) 3_656 . ?
O1W K1 N2 105.21(10) 3_655 . ?
O2WB K1 N2 145.2(5) 3_656 . ?
O2WA K1 O3 85.6(2) . 3_656 ?
O5 K1 O3 66.85(7) . 3_656 ?
O2 K1 O3 49.97(6) 3_656 3_656 ?
O1W K1 O3 134.37(9) 3_655 3_656 ?
O2WB K1 O3 89.2(2) 3_656 3_656 ?
N2 K1 O3 76.27(7) . 3_656 ?
O2WA K1 C6 127.9(2) . . ?
O5 K1 C6 108.55(7) . . ?
O2 K1 C6 80.47(8) 3_656 . ?
O1W K1 C6 107.93(11) 3_655 . ?
O2WB K1 C6 160.8(3) 3_656 . ?
N2 K1 C6 51.54(7) . . ?
O3 K1 C6 107.53(7) 3_656 . ?
O2WA K1 C11 105.6(2) . . ?
O5 K1 C11 127.11(8) . . ?
O2 K1 C11 60.20(7) 3_656 . ?
O1W K1 C11 124.05(11) 3_655 . ?
O2WB K1 C11 146.1(6) 3_656 . ?
N2 K1 C11 68.36(8) . . ?
O3 K1 C11 99.37(7) 3_656 . ?
C6 K1 C11 24.06(8) . . ?
O2WA K1 C10 85.7(2) . . ?
O5 K1 C10 150.45(8) . . ?
O2 K1 C10 63.38(8) 3_656 . ?
O1W K1 C10 113.88(11) 3_655 . ?
O2WB K1 C10 123.0(5) 3_656 . ?
N2 K1 C10 91.75(8) . . ?
O3 K1 C10 111.64(8) 3_656 . ?
C6 K1 C10 42.31(8) . . ?
C11 K1 C10 24.06(8) . . ?
O2WA K1 C7 127.57(19) . . ?
O5 K1 C7 107.80(8) . . ?
O2 K1 C7 102.16(8) 3_656 . ?
O1W K1 C7 84.43(11) 3_655 . ?
O2WB K1 C7 140.6(2) 3_656 . ?
N2 K1 C7 61.88(8) . . ?
O3 K1 C7 130.26(7) 3_656 . ?
C6 K1 C7 24.01(8) . . ?
C11 K1 C7 42.10(9) . . ?
C10 K1 C7 48.91(9) . . ?
O2WA K1 C9 85.7(2) . . ?
O5 K1 C9 148.44(9) . . ?
O2 K1 C9 85.82(9) 3_656 . ?
O1W K1 C9 90.15(11) 3_655 . ?
O2WB K1 C9 112.2(4) 3_656 . ?
N2 K1 C9 100.05(8) . . ?
O3 K1 C9 135.16(9) 3_656 . ?
C6 K1 C9 49.10(8) . . ?
C11 K1 C9 42.06(9) . . ?
C10 K1 C9 23.77(9) . . ?
C7 K1 C9 41.94(9) . . ?
C5 N1 N2 116.5(3) . . ?
C5 N1 V1 128.5(2) . . ?
N2 N1 V1 114.88(18) . . ?
O3 C1 N3 123.0(3) . . ?
O3 C1 C2 130.1(3) . . ?
N3 C1 C2 106.8(3) . . ?
V1 O2 K1 114.29(12) . 3_656 ?
K1 O2WA H2WA 117.7 . . ?
K1 O2WB H2WB 140.1 3_656 . ?
C18 N2 N1 108.5(3) . . ?
C18 N2 K1 116.7(2) . . ?
N1 N2 K1 134.38(18) . . ?
C1 C2 C5 122.8(3) . . ?
C1 C2 C3 105.3(3) . . ?
C5 C2 C3 131.9(3) . . ?
C1 N3 N4 111.4(3) . . ?
C1 N3 C12 127.9(3) . . ?
N4 N3 C12 120.6(3) . . ?
C1 O3 V1 122.5(2) . . ?
C1 O3 K1 141.55(19) . 3_656 ?
V1 O3 K1 89.17(8) . 3_656 ?
N4 C3 C2 110.4(3) . . ?
N4 C3 C4 119.3(3) . . ?
C2 C3 C4 130.2(3) . . ?
C3 N4 N3 106.1(2) . . ?
C18 O4 V1 119.05(19) . . ?
C3 C4 H4C 109.5 . . ?
C3 C4 H4B 109.5 . . ?
H4C C4 H4B 109.5 . . ?
C3 C4 H4A 109.5 . . ?
H4C C4 H4A 109.5 . . ?
H4B C4 H4A 109.5 . . ?
C19 O5 C22 106.0(3) . . ?
C19 O5 K1 121.85(18) . . ?
C22 O5 K1 126.7(2) . . ?
N1 C5 C2 118.1(3) . . ?
N1 C5 C6 122.0(3) . . ?
C2 C5 C6 119.9(3) . . ?
C11 C6 C7 120.0(3) . . ?
C11 C6 C5 119.7(3) . . ?
C7 C6 C5 120.3(3) . . ?
C11 C6 K1 78.63(18) . . ?
C7 C6 K1 79.50(19) . . ?
C5 C6 K1 113.51(17) . . ?
C6 C7 C8 119.6(3) . . ?
C6 C7 K1 76.50(18) . . ?
C8 C7 K1 79.2(2) . . ?
C6 C7 H7 120.2 . . ?
C8 C7 H7 120.2 . . ?
K1 C7 H7 114.8 . . ?
C9 C8 C7 120.3(4) . . ?
C9 C8 K1 77.2(2) . . ?
C7 C8 K1 76.9(2) . . ?
C9 C8 H8 119.9 . . ?
C7 C8 H8 119.9 . . ?
K1 C8 H8 116.7 . . ?
C8 C9 C10 120.1(3) . . ?
C8 C9 K1 79.2(2) . . ?
C10 C9 K1 77.3(2) . . ?
C8 C9 H9 120.0 . . ?
C10 C9 H9 120.0 . . ?
K1 C9 H9 114.1 . . ?
C9 C10 C11 120.3(3) . . ?
C9 C10 K1 78.9(2) . . ?
C11 C10 K1 77.8(2) . . ?
C9 C10 H10 119.9 . . ?
C11 C10 H10 119.9 . . ?
K1 C10 H10 113.9 . . ?
C6 C11 C10 119.8(3) . . ?
C6 C11 K1 77.31(18) . . ?
C10 C11 K1 78.1(2) . . ?
C6 C11 H11 120.1 . . ?
C10 C11 H11 120.1 . . ?
K1 C11 H11 115.1 . . ?
C13 C12 C17 120.7(3) . . ?
C13 C12 N3 120.2(3) . . ?
C17 C12 N3 119.0(3) . . ?
C12 C13 C14 120.0(4) . . ?
C12 C13 H13 120.0 . . ?
C14 C13 H13 120.0 . . ?
C15 C14 C13 119.5(4) . . ?
C15 C14 H14 120.2 . . ?
C13 C14 H14 120.2 . . ?
C16 C15 C14 120.7(4) . . ?
C16 C15 H15 119.7 . . ?
C14 C15 H15 119.7 . . ?
C15 C16 C17 120.6(4) . . ?
C15 C16 H16 119.7 . . ?
C17 C16 H16 119.7 . . ?
C12 C17 C16 118.4(4) . . ?
C12 C17 H17 120.8 . . ?
C16 C17 H17 120.8 . . ?
N2 C18 O4 124.1(3) . . ?
N2 C18 C19 120.7(3) . . ?
O4 C18 C19 115.3(3) . . ?
C20 C19 O5 109.1(3) . . ?
C20 C19 C18 133.2(3) . . ?
O5 C19 C18 117.7(3) . . ?
C19 C20 C21 107.3(3) . . ?
C19 C20 H20 126.3 . . ?
C21 C20 H20 126.3 . . ?
C22 C21 C20 106.9(3) . . ?
C22 C21 H21 126.6 . . ?
C20 C21 H21 126.6 . . ?
C21 C22 O5 110.7(3) . . ?
C21 C22 H22 124.6 . . ?
O5 C22 H22 124.6 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 V1 N1 C5 74.7(3) . . . . ?
O2 V1 N1 C5 -113.3(3) . . . . ?
O3 V1 N1 C5 -28.8(3) . . . . ?
O4 V1 N1 C5 176.8(3) . . . . ?
K1 V1 N1 C5 -83.4(3) 3_656 . . . ?
O1 V1 N1 N2 -101.2(2) . . . . ?
O2 V1 N1 N2 70.9(3) . . . . ?
O3 V1 N1 N2 155.3(2) . . . . ?
O4 V1 N1 N2 0.93(19) . . . . ?
K1 V1 N1 N2 100.74(19) 3_656 . . . ?
O1 V1 O2 K1 -144.07(12) . . . 3_656 ?
O3 V1 O2 K1 -37.83(11) . . . 3_656 ?
O4 V1 O2 K1 108.35(11) . . . 3_656 ?
N1 V1 O2 K1 44.0(2) . . . 3_656 ?
C5 N1 N2 C18 -175.7(3) . . . . ?
V1 N1 N2 C18 0.7(3) . . . . ?
C5 N1 N2 K1 11.9(4) . . . . ?
V1 N1 N2 K1 -171.77(13) . . . . ?
O2WA K1 N2 C18 -88.1(6) . . . . ?
O5 K1 N2 C18 12.4(2) . . . . ?
O2 K1 N2 C18 -107.1(2) 3_656 . . . ?
O1W K1 N2 C18 74.1(2) 3_655 . . . ?
O2WB K1 N2 C18 9.1(8) 3_656 . . . ?
O3 K1 N2 C18 -58.7(2) 3_656 . . . ?
C6 K1 N2 C18 175.2(3) . . . . ?
C11 K1 N2 C18 -164.8(2) . . . . ?
C10 K1 N2 C18 -170.5(2) . . . . ?
C7 K1 N2 C18 149.1(2) . . . . ?
C9 K1 N2 C18 167.1(2) . . . . ?
O2WA K1 N2 N1 83.8(6) . . . . ?
O5 K1 N2 N1 -175.7(3) . . . . ?
O2 K1 N2 N1 64.8(3) 3_656 . . . ?
O1W K1 N2 N1 -113.9(3) 3_655 . . . ?
O2WB K1 N2 N1 -178.9(8) 3_656 . . . ?
O3 K1 N2 N1 113.3(3) 3_656 . . . ?
C6 K1 N2 N1 -12.9(2) . . . . ?
C11 K1 N2 N1 7.2(2) . . . . ?
C10 K1 N2 N1 1.4(3) . . . . ?
C7 K1 N2 N1 -38.9(2) . . . . ?
C9 K1 N2 N1 -21.0(3) . . . . ?
O3 C1 C2 C5 1.1(5) . . . . ?
N3 C1 C2 C5 179.1(3) . . . . ?
O3 C1 C2 C3 -177.3(3) . . . . ?
N3 C1 C2 C3 0.7(3) . . . . ?
O3 C1 N3 N4 177.4(3) . . . . ?
C2 C1 N3 N4 -0.8(3) . . . . ?
O3 C1 N3 C12 -5.2(5) . . . . ?
C2 C1 N3 C12 176.6(3) . . . . ?
N3 C1 O3 V1 145.5(2) . . . . ?
C2 C1 O3 V1 -36.8(4) . . . . ?
N3 C1 O3 K1 -73.7(4) . . . 3_656 ?
C2 C1 O3 K1 104.1(4) . . . 3_656 ?
O1 V1 O3 C1 -65.4(3) . . . . ?
O2 V1 O3 C1 -174.6(2) . . . . ?
O4 V1 O3 C1 86.5(3) . . . . ?
N1 V1 O3 C1 39.2(2) . . . . ?
K1 V1 O3 C1 156.9(3) 3_656 . . . ?
O1 V1 O3 K1 137.71(10) . . . 3_656 ?
O2 V1 O3 K1 28.53(9) . . . 3_656 ?
O4 V1 O3 K1 -70.37(17) . . . 3_656 ?
N1 V1 O3 K1 -117.72(8) . . . 3_656 ?
C1 C2 C3 N4 -0.4(3) . . . . ?
C5 C2 C3 N4 -178.6(3) . . . . ?
C1 C2 C3 C4 -176.3(3) . . . . ?
C5 C2 C3 C4 5.5(6) . . . . ?
C2 C3 N4 N3 -0.1(3) . . . . ?
C4 C3 N4 N3 176.3(3) . . . . ?
C1 N3 N4 C3 0.6(3) . . . . ?
C12 N3 N4 C3 -177.1(3) . . . . ?
O1 V1 O4 C18 99.6(2) . . . . ?
O2 V1 O4 C18 -150.8(2) . . . . ?
O3 V1 O4 C18 -52.2(3) . . . . ?
N1 V1 O4 C18 -2.5(2) . . . . ?
K1 V1 O4 C18 -109.5(2) 3_656 . . . ?
O2WA K1 O5 C19 137.5(3) . . . . ?
O2 K1 O5 C19 55.7(2) 3_656 . . . ?
O1W K1 O5 C19 -136.6(2) 3_655 . . . ?
O2WB K1 O5 C19 160.0(5) 3_656 . . . ?
N2 K1 O5 C19 -18.1(2) . . . . ?
O3 K1 O5 C19 69.4(2) 3_656 . . . ?
C6 K1 O5 C19 -32.2(2) . . . . ?
C11 K1 O5 C19 -14.8(2) . . . . ?
C10 K1 O5 C19 -23.9(3) . . . . ?
C7 K1 O5 C19 -57.5(2) . . . . ?
C9 K1 O5 C19 -71.6(3) . . . . ?
O2WA K1 O5 C22 -12.7(4) . . . . ?
O2 K1 O5 C22 -94.5(3) 3_656 . . . ?
O1W K1 O5 C22 73.2(3) 3_655 . . . ?
O2WB K1 O5 C22 9.8(5) 3_656 . . . ?
N2 K1 O5 C22 -168.3(3) . . . . ?
O3 K1 O5 C22 -80.8(3) 3_656 . . . ?
C6 K1 O5 C22 177.6(3) . . . . ?
C11 K1 O5 C22 -165.0(3) . . . . ?
C10 K1 O5 C22 -174.2(3) . . . . ?
C7 K1 O5 C22 152.3(3) . . . . ?
C9 K1 O5 C22 138.2(3) . . . . ?
N2 N1 C5 C2 -175.8(3) . . . . ?
V1 N1 C5 C2 8.3(4) . . . . ?
N2 N1 C5 C6 3.5(4) . . . . ?
V1 N1 C5 C6 -172.3(2) . . . . ?
C1 C2 C5 N1 12.5(4) . . . . ?
C3 C2 C5 N1 -169.6(3) . . . . ?
C1 C2 C5 C6 -166.8(3) . . . . ?
C3 C2 C5 C6 11.1(5) . . . . ?
N1 C5 C6 C11 -102.7(4) . . . . ?
C2 C5 C6 C11 76.6(4) . . . . ?
N1 C5 C6 C7 78.7(4) . . . . ?
C2 C5 C6 C7 -102.0(4) . . . . ?
N1 C5 C6 K1 -12.7(4) . . . . ?
C2 C5 C6 K1 166.6(2) . . . . ?
O2WA K1 C6 C11 -25.0(4) . . . . ?
O5 K1 C6 C11 144.03(19) . . . . ?
O2 K1 C6 C11 30.71(19) 3_656 . . . ?
O1W K1 C6 C11 -136.0(2) 3_655 . . . ?
O2WB K1 C6 C11 -76.1(19) 3_656 . . . ?
N2 K1 C6 C11 128.6(2) . . . . ?
O3 K1 C6 C11 73.2(2) 3_656 . . . ?
C10 K1 C6 C11 -29.91(19) . . . . ?
C7 K1 C6 C11 -123.7(3) . . . . ?
C9 K1 C6 C11 -62.0(2) . . . . ?
O2WA K1 C6 C7 98.7(4) . . . . ?
O5 K1 C6 C7 -92.2(2) . . . . ?
O2 K1 C6 C7 154.4(2) 3_656 . . . ?
O1W K1 C6 C7 -12.2(2) 3_655 . . . ?
O2WB K1 C6 C7 47.6(19) 3_656 . . . ?
N2 K1 C6 C7 -107.7(2) . . . . ?
O3 K1 C6 C7 -163.03(19) 3_656 . . . ?
C11 K1 C6 C7 123.7(3) . . . . ?
C10 K1 C6 C7 93.8(2) . . . . ?
C9 K1 C6 C7 61.7(2) . . . . ?
O2WA K1 C6 C5 -142.6(3) . . . . ?
O5 K1 C6 C5 26.4(2) . . . . ?
O2 K1 C6 C5 -86.9(2) 3_656 . . . ?
O1W K1 C6 C5 106.4(2) 3_655 . . . ?
O2WB K1 C6 C5 166.3(19) 3_656 . . . ?
N2 K1 C6 C5 10.95(18) . . . . ?
O3 K1 C6 C5 -44.4(2) 3_656 . . . ?
C11 K1 C6 C5 -117.6(3) . . . . ?
C10 K1 C6 C5 -147.5(3) . . . . ?
C7 K1 C6 C5 118.6(3) . . . . ?
C9 K1 C6 C5 -179.6(3) . . . . ?
C11 C6 C7 C8 1.2(5) . . . . ?
C5 C6 C7 C8 179.8(3) . . . . ?
K1 C6 C7 C8 -69.0(3) . . . . ?
C11 C6 C7 K1 70.2(3) . . . . ?
C5 C6 C7 K1 -111.2(3) . . . . ?
O2WA K1 C7 C6 -100.2(4) . . . . ?
O5 K1 C7 C6 95.8(2) . . . . ?
O2 K1 C7 C6 -25.8(2) 3_656 . . . ?
O1W K1 C7 C6 168.3(2) 3_655 . . . ?
O2WB K1 C7 C6 -157.5(10) 3_656 . . . ?
N2 K1 C7 C6 57.76(19) . . . . ?
O3 K1 C7 C6 21.4(2) 3_656 . . . ?
C11 K1 C7 C6 -30.38(18) . . . . ?
C10 K1 C7 C6 -63.0(2) . . . . ?
C9 K1 C7 C6 -95.2(2) . . . . ?
O2WA K1 C7 C8 24.1(4) . . . . ?
O5 K1 C7 C8 -139.9(2) . . . . ?
O2 K1 C7 C8 98.5(2) 3_656 . . . ?
O1W K1 C7 C8 -67.4(2) 3_655 . . . ?
O2WB K1 C7 C8 -33.2(11) 3_656 . . . ?
N2 K1 C7 C8 -177.9(3) . . . . ?
O3 K1 C7 C8 145.7(2) 3_656 . . . ?
C6 K1 C7 C8 124.3(3) . . . . ?
C11 K1 C7 C8 93.9(2) . . . . ?
C10 K1 C7 C8 61.3(2) . . . . ?
C9 K1 C7 C8 29.1(2) . . . . ?
C6 C7 C8 C9 1.0(5) . . . . ?
K1 C7 C8 C9 -66.5(3) . . . . ?
C6 C7 C8 K1 67.5(3) . . . . ?
O2WA K1 C8 C9 -34.7(3) . . . . ?
O5 K1 C8 C9 174.2(2) . . . . ?
O2 K1 C8 C9 38.4(2) 3_656 . . . ?
O1W K1 C8 C9 -125.7(3) 3_655 . . . ?
O2WB K1 C8 C9 -77.9(8) 3_656 . . . ?
N2 K1 C8 C9 127.5(2) . . . . ?
O3 K1 C8 C9 71.9(3) 3_656 . . . ?
C6 K1 C8 C9 95.6(3) . . . . ?
C11 K1 C8 C9 62.8(2) . . . . ?
C10 K1 C8 C9 30.0(2) . . . . ?
C7 K1 C8 C9 125.7(4) . . . . ?
O2WA K1 C8 C7 -160.4(3) . . . . ?
O5 K1 C8 C7 48.5(3) . . . . ?
O2 K1 C8 C7 -87.2(2) 3_656 . . . ?
O1W K1 C8 C7 108.7(2) 3_655 . . . ?
O2WB K1 C8 C7 156.5(8) 3_656 . . . ?
N2 K1 C8 C7 1.8(2) . . . . ?
O3 K1 C8 C7 -53.8(3) 3_656 . . . ?
C6 K1 C8 C7 -30.1(2) . . . . ?
C11 K1 C8 C7 -62.9(2) . . . . ?
C10 K1 C8 C7 -95.6(3) . . . . ?
C9 K1 C8 C7 -125.7(4) . . . . ?
C7 C8 C9 C10 -1.9(6) . . . . ?
K1 C8 C9 C10 -68.3(3) . . . . ?
C7 C8 C9 K1 66.4(3) . . . . ?
O2WA K1 C9 C8 146.6(3) . . . . ?
O5 K1 C9 C8 -9.2(3) . . . . ?
O2 K1 C9 C8 -142.9(2) 3_656 . . . ?
O1W K1 C9 C8 52.0(2) 3_655 . . . ?
O2WB K1 C9 C8 113.2(7) 3_656 . . . ?
N2 K1 C9 C8 -53.5(2) . . . . ?
O3 K1 C9 C8 -134.1(2) 3_656 . . . ?
C6 K1 C9 C8 -61.9(2) . . . . ?
C11 K1 C9 C8 -94.4(3) . . . . ?
C10 K1 C9 C8 -124.5(3) . . . . ?
C7 K1 C9 C8 -29.5(2) . . . . ?
O2WA K1 C9 C10 -89.0(3) . . . . ?
O5 K1 C9 C10 115.3(2) . . . . ?
O2 K1 C9 C10 -18.4(2) 3_656 . . . ?
O1W K1 C9 C10 176.5(2) 3_655 . . . ?
O2WB K1 C9 C10 -122.4(7) 3_656 . . . ?
N2 K1 C9 C10 71.0(2) . . . . ?
O3 K1 C9 C10 -9.6(3) 3_656 . . . ?
C6 K1 C9 C10 62.6(2) . . . . ?
C11 K1 C9 C10 30.1(2) . . . . ?
C7 K1 C9 C10 95.0(2) . . . . ?
C8 C9 C10 C11 0.7(5) . . . . ?
K1 C9 C10 C11 -68.7(3) . . . . ?
C8 C9 C10 K1 69.4(3) . . . . ?
O2WA K1 C10 C9 89.2(3) . . . . ?
O5 K1 C10 C9 -106.4(3) . . . . ?
O2 K1 C10 C9 159.4(2) 3_656 . . . ?
O1W K1 C10 C9 -3.9(3) 3_655 . . . ?
O2WB K1 C10 C9 68.9(6) 3_656 . . . ?
N2 K1 C10 C9 -111.4(2) . . . . ?
O3 K1 C10 C9 172.7(2) 3_656 . . . ?
C6 K1 C10 C9 -94.7(2) . . . . ?
C11 K1 C10 C9 -124.6(3) . . . . ?
C7 K1 C10 C9 -62.1(2) . . . . ?
O2WA K1 C10 C11 -146.2(3) . . . . ?
O5 K1 C10 C11 18.2(3) . . . . ?
O2 K1 C10 C11 -76.1(2) 3_656 . . . ?
O1W K1 C10 C11 120.7(2) 3_655 . . . ?
O2WB K1 C10 C11 -166.5(5) 3_656 . . . ?
N2 K1 C10 C11 13.2(2) . . . . ?
O3 K1 C10 C11 -62.7(2) 3_656 . . . ?
C6 K1 C10 C11 29.92(19) . . . . ?
C7 K1 C10 C11 62.5(2) . . . . ?
C9 K1 C10 C11 124.6(3) . . . . ?
C7 C6 C11 C10 -2.5(5) . . . . ?
C5 C6 C11 C10 178.9(3) . . . . ?
K1 C6 C11 C10 68.2(3) . . . . ?
C7 C6 C11 K1 -70.7(3) . . . . ?
C5 C6 C11 K1 110.7(2) . . . . ?
C9 C10 C11 C6 1.6(5) . . . . ?
K1 C10 C11 C6 -67.7(3) . . . . ?
C9 C10 C11 K1 69.3(3) . . . . ?
O2WA K1 C11 C6 159.7(3) . . . . ?
O5 K1 C11 C6 -44.3(2) . . . . ?
O2 K1 C11 C6 -144.5(2) 3_656 . . . ?
O1W K1 C11 C6 53.0(2) 3_655 . . . ?
O2WB K1 C11 C6 145.1(6) 3_656 . . . ?
N2 K1 C11 C6 -41.20(18) . . . . ?
O3 K1 C11 C6 -112.27(19) 3_656 . . . ?
C10 K1 C11 C6 124.6(3) . . . . ?
C7 K1 C11 C6 30.31(17) . . . . ?
C9 K1 C11 C6 94.9(2) . . . . ?
O2WA K1 C11 C10 35.2(3) . . . . ?
O5 K1 C11 C10 -168.9(2) . . . . ?
O2 K1 C11 C10 90.9(2) 3_656 . . . ?
O1W K1 C11 C10 -71.6(2) 3_655 . . . ?
O2WB K1 C11 C10 20.5(7) 3_656 . . . ?
N2 K1 C11 C10 -165.8(2) . . . . ?
O3 K1 C11 C10 123.2(2) 3_656 . . . ?
C6 K1 C11 C10 -124.6(3) . . . . ?
C7 K1 C11 C10 -94.3(2) . . . . ?
C9 K1 C11 C10 -29.7(2) . . . . ?
C1 N3 C12 C13 -29.6(5) . . . . ?
N4 N3 C12 C13 147.6(3) . . . . ?
C1 N3 C12 C17 152.3(3) . . . . ?
N4 N3 C12 C17 -30.5(4) . . . . ?
C17 C12 C13 C14 -1.9(6) . . . . ?
N3 C12 C13 C14 -180.0(3) . . . . ?
C12 C13 C14 C15 1.9(6) . . . . ?
C13 C14 C15 C16 -0.7(7) . . . . ?
C14 C15 C16 C17 -0.5(7) . . . . ?
C13 C12 C17 C16 0.7(6) . . . . ?
N3 C12 C17 C16 178.8(3) . . . . ?
C15 C16 C17 C12 0.5(6) . . . . ?
N1 N2 C18 O4 -3.0(4) . . . . ?
K1 N2 C18 O4 170.9(2) . . . . ?
N1 N2 C18 C19 179.1(3) . . . . ?
K1 N2 C18 C19 -7.0(4) . . . . ?
V1 O4 C18 N2 4.2(4) . . . . ?
V1 O4 C18 C19 -177.8(2) . . . . ?
C22 O5 C19 C20 0.0(4) . . . . ?
K1 O5 C19 C20 -155.5(2) . . . . ?
C22 O5 C19 C18 178.9(3) . . . . ?
K1 O5 C19 C18 23.4(4) . . . . ?
N2 C18 C19 C20 168.9(4) . . . . ?
O4 C18 C19 C20 -9.2(6) . . . . ?
N2 C18 C19 O5 -9.7(4) . . . . ?
O4 C18 C19 O5 172.2(3) . . . . ?
O5 C19 C20 C21 0.1(4) . . . . ?
C18 C19 C20 C21 -178.5(3) . . . . ?
C19 C20 C21 C22 -0.2(4) . . . . ?
C20 C21 C22 O5 0.2(4) . . . . ?
C19 O5 C22 C21 -0.2(4) . . . . ?
K1 O5 C22 C21 153.8(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
O1W H1WA O4 0.85 2.16 3.004(4) 173.3 .

_diffrn_measured_fraction_theta_max 0.972
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.626
_refine_diff_density_min         -0.779
_refine_diff_density_rms         0.198
####################################################################### 
# 
# 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_compound7
_database_code_depnum_ccdc_archive 'CCDC 1502025'
_audit_update_record             
;
2016-09-01 deposited with the CCDC.
2016-09-15 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C24 H19 N4 O4 V, 1.5(H2 O)'
_chemical_formula_sum            'C24 H22 N4 O5.50 V'
_chemical_formula_weight         505.40

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

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   P-1
_symmetry_space_group_name_Hall  -P1

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

_cell_length_a                   8.5590(16)
_cell_length_b                   10.2574(18)
_cell_length_c                   14.448(2)
_cell_angle_alpha                83.719(11)
_cell_angle_beta                 78.317(11)
_cell_angle_gamma                71.534(11)
_cell_volume                     1176.8(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    34619
_cell_measurement_theta_min      4.970
_cell_measurement_theta_max      38.550

_exptl_crystal_description       prism
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.08
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.426
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             522
_exptl_absorpt_coefficient_mu    0.467
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9269
_exptl_absorpt_correction_T_max  0.9641
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            24559
_diffrn_reflns_av_R_equivalents  0.0706
_diffrn_reflns_av_unetI/netI     0.0886
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         1.44
_diffrn_reflns_theta_max         26.43
_reflns_number_total             4742
_reflns_number_gt                2533
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Apex2, Bruker Instrument Service v2010, 1-2'
_computing_cell_refinement       
'SAINT V7.68A (Bruker: Madison, 2009 ) in Apex2 suite'
_computing_data_reduction        
'SAINT and XPREP Version 2008/2 (Sheldrick, Bruker AXS Inc.)'
_computing_structure_solution    
'XS V2008/1 (G. M. Sheldrick, Acta Cryst. (2008). A64, 112-122)'
_computing_structure_refinement  
'XL V2008/4 (G. M. Sheldrick, Acta Cryst. (2008). A64, 112-122)'
_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)+(0.1420P)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    mixed
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.025(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         4742
_refine_ls_number_parameters     327
_refine_ls_number_restraints     6
_refine_ls_R_factor_all          0.1261
_refine_ls_R_factor_gt           0.0691
_refine_ls_wR_factor_ref         0.2376
_refine_ls_wR_factor_gt          0.1999
_refine_ls_goodness_of_fit_ref   0.993
_refine_ls_restrained_S_all      0.993
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
V1 V 0.08792(9) 0.73429(7) 0.31890(5) 0.0476(4) Uani 1 1 d . . .
O1 O 0.2192(4) 0.8180(4) 0.2838(3) 0.0707(11) Uani 1 1 d . . .
N1 N 0.2238(4) 0.5165(4) 0.3126(3) 0.0450(9) Uani 1 1 d . . .
C1 C 0.1177(5) 0.6218(4) 0.1419(3) 0.0432(11) Uani 1 1 d . . .
O1W O 0.2789(6) 0.1870(4) 0.4633(3) 0.1047(16) Uani 1 1 d . . .
H1WB H 0.2276 0.1867 0.5202 0.157 Uiso 1 1 d R . .
H1WA H 0.3792 0.1421 0.4684 0.157 Uiso 1 1 d R . .
O2 O -0.0903(4) 0.8405(4) 0.3613(2) 0.0676(10) Uani 1 1 d . . .
C2 C 0.2427(5) 0.4953(5) 0.1516(3) 0.0452(11) Uani 1 1 d . . .
N2 N 0.2554(4) 0.4574(4) 0.4023(2) 0.0449(9) Uani 1 1 d . . .
H2N H 0.3031 0.3688 0.4127 0.054 Uiso 1 1 calc R . .
O2W O 0.325(2) -0.0974(15) 0.4700(10) 0.090(5) Uani 0.25 1 d P . .
H2WB H 0.2497 -0.0757 0.4337 0.135 Uiso 0.25 1 d PR . .
H2WA H 0.2994 -0.1532 0.5162 0.135 Uiso 0.25 1 d PR . .
O3 O 0.0251(4) 0.7047(3) 0.2049(2) 0.0502(8) Uani 1 1 d . . .
N3 N 0.1033(4) 0.6418(4) 0.0497(3) 0.0480(10) Uani 1 1 d . . .
C3 C 0.3030(5) 0.4495(5) 0.0562(3) 0.0479(11) Uani 1 1 d . . .
O3W O 0.0425(13) 0.0760(10) 0.4014(7) 0.038(3) Uani 0.25 1 d PU . .
H3WB H 0.1020 0.0708 0.4447 0.057 Uiso 0.25 1 d PR . .
H3WA H -0.0602 0.0830 0.4282 0.057 Uiso 0.25 1 d PR . .
O4 O 0.1317(4) 0.6698(3) 0.4491(2) 0.0600(9) Uani 1 1 d . . .
N4 N 0.2192(5) 0.5364(4) -0.0037(3) 0.0514(10) Uani 1 1 d . . .
C4 C 0.4410(6) 0.3281(5) 0.0208(3) 0.0575(13) Uani 1 1 d . . .
H4C H 0.4013 0.2471 0.0304 0.086 Uiso 1 1 calc R . .
H4B H 0.5333 0.3129 0.0554 0.086 Uiso 1 1 calc R . .
H4A H 0.4804 0.3437 -0.0468 0.086 Uiso 1 1 calc R . .
C5 C 0.2861(5) 0.4378(4) 0.2395(3) 0.0414(10) Uani 1 1 d . . .
C6 C 0.3916(5) 0.2938(4) 0.2496(3) 0.0423(11) Uani 1 1 d . . .
C7 C 0.3410(6) 0.1884(5) 0.2298(3) 0.0501(12) Uani 1 1 d . . .
H7 H 0.2381 0.2075 0.2080 0.060 Uiso 1 1 calc R . .
C8 C 0.4400(6) 0.0516(5) 0.2416(3) 0.0570(13) Uani 1 1 d . . .
H8 H 0.4039 -0.0216 0.2279 0.068 Uiso 1 1 calc R . .
C9 C 0.5880(6) 0.0236(5) 0.2726(3) 0.0560(13) Uani 1 1 d . . .
H9 H 0.6547 -0.0690 0.2810 0.067 Uiso 1 1 calc R . .
C10 C 0.6400(6) 0.1287(5) 0.2913(4) 0.0594(14) Uani 1 1 d . . .
H10 H 0.7446 0.1086 0.3112 0.071 Uiso 1 1 calc R . .
C11 C 0.5436(5) 0.2641(5) 0.2819(3) 0.0506(12) Uani 1 1 d . . .
H11 H 0.5798 0.3363 0.2971 0.061 Uiso 1 1 calc R . .
C12 C 0.2073(5) 0.5460(5) 0.4690(3) 0.0476(11) Uani 1 1 d . . .
C13 C 0.2390(6) 0.5027(5) 0.5667(3) 0.0516(12) Uani 1 1 d . . .
C14 C 0.3717(6) 0.3931(5) 0.5854(4) 0.0617(14) Uani 1 1 d . . .
H14 H 0.4450 0.3394 0.5355 0.074 Uiso 1 1 calc R . .
C15 C 0.3980(8) 0.3611(6) 0.6777(5) 0.0743(18) Uani 1 1 d . . .
H15 H 0.4905 0.2858 0.6911 0.089 Uiso 1 1 calc R . .
C16 C 0.2916(8) 0.4374(7) 0.7496(4) 0.0764(17) Uani 1 1 d . . .
H16 H 0.3104 0.4153 0.8128 0.092 Uiso 1 1 calc R . .
C17 C 0.1594(7) 0.5443(7) 0.7308(4) 0.0675(15) Uani 1 1 d . . .
H17 H 0.0842 0.5951 0.7816 0.081 Uiso 1 1 calc R . .
C18 C 0.1319(6) 0.5806(6) 0.6403(3) 0.0574(13) Uani 1 1 d . . .
H18 H 0.0409 0.6579 0.6278 0.069 Uiso 1 1 calc R . .
C19 C 0.0015(6) 0.7595(5) 0.0054(3) 0.0466(11) Uani 1 1 d . . .
C20 C -0.1541(6) 0.8288(5) 0.0529(3) 0.0551(13) Uani 1 1 d . . .
H20 H -0.1970 0.7945 0.1132 0.066 Uiso 1 1 calc R . .
C21 C -0.2487(6) 0.9499(5) 0.0119(4) 0.0602(13) Uani 1 1 d . . .
H21 H -0.3552 0.9997 0.0450 0.072 Uiso 1 1 calc R . .
C22 C -0.1887(6) 0.9970(5) -0.0753(4) 0.0599(14) Uani 1 1 d . . .
H22 H -0.2536 1.0789 -0.1035 0.072 Uiso 1 1 calc R . .
C23 C -0.0331(6) 0.9253(5) -0.1228(3) 0.0621(14) Uani 1 1 d . . .
H23 H 0.0086 0.9580 -0.1839 0.074 Uiso 1 1 calc R . .
C24 C 0.0618(6) 0.8072(5) -0.0825(3) 0.0560(13) Uani 1 1 d . . .
H24 H 0.1691 0.7586 -0.1154 0.067 Uiso 1 1 calc R . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
V1 O1 1.594(3) . ?
V1 O2 1.613(3) . ?
V1 O3 1.914(3) . ?
V1 O4 1.993(3) . ?
V1 N1 2.169(4) . ?
N1 C5 1.318(5) . ?
N1 N2 1.410(5) . ?
C1 O3 1.277(5) . ?
C1 N3 1.350(5) . ?
C1 C2 1.411(6) . ?
O1W H1WB 0.8501 . ?
O1W H1WA 0.8501 . ?
C2 C5 1.410(6) . ?
C2 C3 1.444(6) . ?
N2 C12 1.310(5) . ?
N2 H2N 0.8800 . ?
O2W H2WB 0.8700 . ?
O2W H2WA 0.8700 . ?
N3 N4 1.394(5) . ?
N3 C19 1.420(5) . ?
C3 N4 1.317(5) . ?
C3 C4 1.473(6) . ?
O3W H3WB 0.8700 . ?
O3W H3WA 0.8700 . ?
O4 C12 1.260(5) . ?
C4 H4C 0.9800 . ?
C4 H4B 0.9800 . ?
C4 H4A 0.9800 . ?
C5 C6 1.477(6) . ?
C6 C7 1.361(6) . ?
C6 C11 1.402(6) . ?
C7 C8 1.403(6) . ?
C7 H7 0.9500 . ?
C8 C9 1.363(7) . ?
C8 H8 0.9500 . ?
C9 C10 1.360(7) . ?
C9 H9 0.9500 . ?
C10 C11 1.380(6) . ?
C10 H10 0.9500 . ?
C11 H11 0.9500 . ?
C12 C13 1.485(6) . ?
C13 C14 1.370(6) . ?
C13 C18 1.392(7) . ?
C14 C15 1.384(7) . ?
C14 H14 0.9500 . ?
C15 C16 1.365(8) . ?
C15 H15 0.9500 . ?
C16 C17 1.353(8) . ?
C16 H16 0.9500 . ?
C17 C18 1.367(7) . ?
C17 H17 0.9500 . ?
C18 H18 0.9500 . ?
C19 C24 1.370(6) . ?
C19 C20 1.374(6) . ?
C20 C21 1.395(6) . ?
C20 H20 0.9500 . ?
C21 C22 1.359(7) . ?
C21 H21 0.9500 . ?
C22 C23 1.380(6) . ?
C22 H22 0.9500 . ?
C23 C24 1.371(6) . ?
C23 H23 0.9500 . ?
C24 H24 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 V1 O2 108.6(2) . . ?
O1 V1 O3 104.09(16) . . ?
O2 V1 O3 96.18(16) . . ?
O1 V1 O4 101.45(17) . . ?
O2 V1 O4 90.84(15) . . ?
O3 V1 O4 149.69(14) . . ?
O1 V1 N1 107.97(16) . . ?
O2 V1 N1 142.36(17) . . ?
O3 V1 N1 83.10(13) . . ?
O4 V1 N1 73.64(13) . . ?
C5 N1 N2 117.9(3) . . ?
C5 N1 V1 130.4(3) . . ?
N2 N1 V1 111.6(3) . . ?
O3 C1 N3 122.9(4) . . ?
O3 C1 C2 129.8(4) . . ?
N3 C1 C2 107.2(4) . . ?
H1WB O1W H1WA 102.5 . . ?
C5 C2 C1 123.0(4) . . ?
C5 C2 C3 132.7(4) . . ?
C1 C2 C3 104.3(4) . . ?
C12 N2 N1 114.0(3) . . ?
C12 N2 H2N 123.0 . . ?
N1 N2 H2N 123.0 . . ?
H2WB O2W H2WA 109.5 . . ?
C1 O3 V1 125.5(3) . . ?
C1 N3 N4 111.3(3) . . ?
C1 N3 C19 127.5(4) . . ?
N4 N3 C19 120.9(4) . . ?
N4 C3 C2 110.8(4) . . ?
N4 C3 C4 119.8(4) . . ?
C2 C3 C4 129.4(4) . . ?
H3WB O3W H3WA 109.5 . . ?
C12 O4 V1 121.8(3) . . ?
C3 N4 N3 106.3(4) . . ?
C3 C4 H4C 109.5 . . ?
C3 C4 H4B 109.5 . . ?
H4C C4 H4B 109.5 . . ?
C3 C4 H4A 109.5 . . ?
H4C C4 H4A 109.5 . . ?
H4B C4 H4A 109.5 . . ?
N1 C5 C2 117.2(4) . . ?
N1 C5 C6 121.6(4) . . ?
C2 C5 C6 121.1(4) . . ?
C7 C6 C11 119.2(4) . . ?
C7 C6 C5 120.6(4) . . ?
C11 C6 C5 120.2(4) . . ?
C6 C7 C8 120.3(4) . . ?
C6 C7 H7 119.8 . . ?
C8 C7 H7 119.8 . . ?
C9 C8 C7 120.0(5) . . ?
C9 C8 H8 120.0 . . ?
C7 C8 H8 120.0 . . ?
C10 C9 C8 119.8(4) . . ?
C10 C9 H9 120.1 . . ?
C8 C9 H9 120.1 . . ?
C9 C10 C11 121.3(4) . . ?
C9 C10 H10 119.4 . . ?
C11 C10 H10 119.4 . . ?
C10 C11 C6 119.3(5) . . ?
C10 C11 H11 120.4 . . ?
C6 C11 H11 120.4 . . ?
O4 C12 N2 118.8(4) . . ?
O4 C12 C13 120.0(4) . . ?
N2 C12 C13 121.2(4) . . ?
C14 C13 C18 119.9(4) . . ?
C14 C13 C12 122.3(5) . . ?
C18 C13 C12 117.8(4) . . ?
C13 C14 C15 119.5(6) . . ?
C13 C14 H14 120.2 . . ?
C15 C14 H14 120.2 . . ?
C16 C15 C14 120.2(5) . . ?
C16 C15 H15 119.9 . . ?
C14 C15 H15 119.9 . . ?
C17 C16 C15 120.0(5) . . ?
C17 C16 H16 120.0 . . ?
C15 C16 H16 120.0 . . ?
C16 C17 C18 121.2(6) . . ?
C16 C17 H17 119.4 . . ?
C18 C17 H17 119.4 . . ?
C17 C18 C13 119.1(5) . . ?
C17 C18 H18 120.5 . . ?
C13 C18 H18 120.5 . . ?
C24 C19 C20 120.3(4) . . ?
C24 C19 N3 120.0(4) . . ?
C20 C19 N3 119.6(4) . . ?
C19 C20 C21 119.4(4) . . ?
C19 C20 H20 120.3 . . ?
C21 C20 H20 120.3 . . ?
C22 C21 C20 120.1(5) . . ?
C22 C21 H21 119.9 . . ?
C20 C21 H21 119.9 . . ?
C21 C22 C23 119.8(4) . . ?
C21 C22 H22 120.1 . . ?
C23 C22 H22 120.1 . . ?
C24 C23 C22 120.5(4) . . ?
C24 C23 H23 119.7 . . ?
C22 C23 H23 119.7 . . ?
C19 C24 C23 119.8(4) . . ?
C19 C24 H24 120.1 . . ?
C23 C24 H24 120.1 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 V1 N1 C5 -76.0(4) . . . . ?
O2 V1 N1 C5 117.8(4) . . . . ?
O3 V1 N1 C5 26.6(4) . . . . ?
O4 V1 N1 C5 -173.0(4) . . . . ?
O1 V1 N1 N2 99.8(3) . . . . ?
O2 V1 N1 N2 -66.4(4) . . . . ?
O3 V1 N1 N2 -157.6(3) . . . . ?
O4 V1 N1 N2 2.8(2) . . . . ?
O3 C1 C2 C5 0.2(7) . . . . ?
N3 C1 C2 C5 -177.0(4) . . . . ?
O3 C1 C2 C3 180.0(4) . . . . ?
N3 C1 C2 C3 2.8(5) . . . . ?
C5 N1 N2 C12 172.0(4) . . . . ?
V1 N1 N2 C12 -4.3(4) . . . . ?
N3 C1 O3 V1 -151.5(3) . . . . ?
C2 C1 O3 V1 31.7(6) . . . . ?
O1 V1 O3 C1 72.1(4) . . . . ?
O2 V1 O3 C1 -176.9(3) . . . . ?
O4 V1 O3 C1 -74.5(4) . . . . ?
N1 V1 O3 C1 -34.8(3) . . . . ?
O3 C1 N3 N4 180.0(4) . . . . ?
C2 C1 N3 N4 -2.6(5) . . . . ?
O3 C1 N3 C19 7.2(7) . . . . ?
C2 C1 N3 C19 -175.3(4) . . . . ?
C5 C2 C3 N4 177.6(4) . . . . ?
C1 C2 C3 N4 -2.1(5) . . . . ?
C5 C2 C3 C4 -4.5(8) . . . . ?
C1 C2 C3 C4 175.8(5) . . . . ?
O1 V1 O4 C12 -106.6(4) . . . . ?
O2 V1 O4 C12 144.2(4) . . . . ?
O3 V1 O4 C12 40.4(5) . . . . ?
N1 V1 O4 C12 -1.0(3) . . . . ?
C2 C3 N4 N3 0.6(5) . . . . ?
C4 C3 N4 N3 -177.5(4) . . . . ?
C1 N3 N4 C3 1.3(5) . . . . ?
C19 N3 N4 C3 174.5(4) . . . . ?
N2 N1 C5 C2 175.2(4) . . . . ?
V1 N1 C5 C2 -9.2(6) . . . . ?
N2 N1 C5 C6 -2.6(6) . . . . ?
V1 N1 C5 C6 173.0(3) . . . . ?
C1 C2 C5 N1 -10.4(6) . . . . ?
C3 C2 C5 N1 170.0(5) . . . . ?
C1 C2 C5 C6 167.4(4) . . . . ?
C3 C2 C5 C6 -12.2(7) . . . . ?
N1 C5 C6 C7 117.4(5) . . . . ?
C2 C5 C6 C7 -60.3(6) . . . . ?
N1 C5 C6 C11 -61.0(6) . . . . ?
C2 C5 C6 C11 121.3(5) . . . . ?
C11 C6 C7 C8 -0.1(7) . . . . ?
C5 C6 C7 C8 -178.5(4) . . . . ?
C6 C7 C8 C9 -0.2(7) . . . . ?
C7 C8 C9 C10 -0.5(7) . . . . ?
C8 C9 C10 C11 1.7(8) . . . . ?
C9 C10 C11 C6 -2.0(7) . . . . ?
C7 C6 C11 C10 1.2(7) . . . . ?
C5 C6 C11 C10 179.6(4) . . . . ?
V1 O4 C12 N2 -1.3(6) . . . . ?
V1 O4 C12 C13 179.3(3) . . . . ?
N1 N2 C12 O4 3.8(6) . . . . ?
N1 N2 C12 C13 -176.7(4) . . . . ?
O4 C12 C13 C14 -152.5(5) . . . . ?
N2 C12 C13 C14 28.1(7) . . . . ?
O4 C12 C13 C18 25.3(6) . . . . ?
N2 C12 C13 C18 -154.1(5) . . . . ?
C18 C13 C14 C15 -0.2(7) . . . . ?
C12 C13 C14 C15 177.6(5) . . . . ?
C13 C14 C15 C16 0.7(8) . . . . ?
C14 C15 C16 C17 0.3(8) . . . . ?
C15 C16 C17 C18 -1.8(8) . . . . ?
C16 C17 C18 C13 2.3(8) . . . . ?
C14 C13 C18 C17 -1.3(7) . . . . ?
C12 C13 C18 C17 -179.1(5) . . . . ?
C1 N3 C19 C24 140.0(5) . . . . ?
N4 N3 C19 C24 -32.1(6) . . . . ?
C1 N3 C19 C20 -36.9(7) . . . . ?
N4 N3 C19 C20 151.0(4) . . . . ?
C24 C19 C20 C21 -1.5(7) . . . . ?
N3 C19 C20 C21 175.4(4) . . . . ?
C19 C20 C21 C22 1.6(8) . . . . ?
C20 C21 C22 C23 -0.7(8) . . . . ?
C21 C22 C23 C24 -0.2(8) . . . . ?
C20 C19 C24 C23 0.5(8) . . . . ?
N3 C19 C24 C23 -176.3(5) . . . . ?
C22 C23 C24 C19 0.3(8) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O1W H1WB O2 0.85 1.92 2.754(5) 167.3 2_566
N2 H2N O1W 0.88 1.99 2.774(5) 148.4 .
O2W H2WB O3W 0.87 2.05 2.80(2) 143.6 .
O2W H2WB O1 0.87 2.62 3.286(16) 134.0 1_545
O3W H3WB O2W 0.87 2.19 2.80(2) 126.7 .
O3W H3WA O2W 0.87 2.41 3.266(19) 169.1 2_556

_diffrn_measured_fraction_theta_max 0.981
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         1.119
_refine_diff_density_min         -0.430
_refine_diff_density_rms         0.115
####################################################################### 
# 
# 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_compound8
_database_code_depnum_ccdc_archive 'CCDC 1502026'
_audit_update_record             
;
2016-09-01 deposited with the CCDC.
2016-09-15 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C22 H17 N4 O5 V'
_chemical_formula_sum            'C22 H17 N4 O5 V'
_chemical_formula_weight         468.34

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   C2/c
_symmetry_space_group_name_Hall  -C2yc

loop_
_symmetry_equiv_pos_as_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                   25.862(3)
_cell_length_b                   7.1899(7)
_cell_length_c                   21.357(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 98.156(5)
_cell_angle_gamma                90.00
_cell_volume                     3931.0(7)
_cell_formula_units_Z            8
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    46640
_cell_measurement_theta_min      4.636
_cell_measurement_theta_max      52.172

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.13
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.583
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1920
_exptl_absorpt_coefficient_mu    0.550
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9171
_exptl_absorpt_correction_T_max  0.9319
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            44518
_diffrn_reflns_av_R_equivalents  0.0474
_diffrn_reflns_av_unetI/netI     0.0233
_diffrn_reflns_limit_h_min       -32
_diffrn_reflns_limit_h_max       32
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_theta_min         1.59
_diffrn_reflns_theta_max         26.38
_reflns_number_total             3989
_reflns_number_gt                3381
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Apex2, Bruker Instrument Service v2010, 1-2'
_computing_cell_refinement       
'SAINT V7.68A (Bruker: Madison, 2009 ) in Apex2 suite'
_computing_data_reduction        
'SAINT and XPREP Version 2008/2 (Sheldrick, Bruker AXS Inc.)'
_computing_structure_solution    
'XS V2008/1 (G. M. Sheldrick, Acta Cryst. (2008). A64, 112-122)'
_computing_structure_refinement  
'XL V2008/4 (G. M. Sheldrick, Acta Cryst. (2008). A64, 112-122)'
_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)+(0.0587P)²+3.9983P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3989
_refine_ls_number_parameters     346
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0406
_refine_ls_R_factor_gt           0.0315
_refine_ls_wR_factor_ref         0.1040
_refine_ls_wR_factor_gt          0.0894
_refine_ls_goodness_of_fit_ref   1.107
_refine_ls_restrained_S_all      1.107
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
V1 V 0.059482(12) 0.17839(4) 0.109657(14) 0.01296(12) Uani 1 1 d . . .
O1 O 0.03348(5) -0.01867(19) 0.12587(6) 0.0169(3) Uani 1 1 d . . .
N1 N 0.06334(6) 0.1884(2) 0.00766(7) 0.0138(3) Uani 1 1 d . . .
C1 C 0.16085(7) 0.0756(3) 0.06976(9) 0.0145(4) Uani 1 1 d . . .
N2 N 0.01383(6) 0.2283(2) -0.02490(8) 0.0147(3) Uani 1 1 d . . .
H2N H 0.0047(10) 0.190(3) -0.0619(13) 0.029(7) Uiso 1 1 d . . .
O2 O 0.06623(5) 0.30747(18) 0.17214(6) 0.0186(3) Uani 1 1 d . . .
C2 C 0.14983(7) 0.0958(3) 0.00327(9) 0.0138(4) Uani 1 1 d . . .
O3 O 0.13260(5) 0.1135(2) 0.11322(6) 0.0174(3) Uani 1 1 d . . .
N3 N 0.21091(6) 0.0149(2) 0.08261(7) 0.0150(3) Uani 1 1 d . . .
C3 C 0.19792(7) 0.0510(3) -0.01918(9) 0.0158(4) Uani 1 1 d . . .
O4 O -0.00737(5) 0.30395(18) 0.07014(6) 0.0160(3) Uani 1 1 d . . .
N4 N 0.23393(6) 0.0028(2) 0.02761(8) 0.0168(3) Uani 1 1 d . . .
C4 C 0.21189(8) 0.0554(3) -0.08497(9) 0.0198(4) Uani 1 1 d . . .
H4C H 0.2487 0.0782 -0.0831 0.030 Uiso 1 1 calc R . .
H4B H 0.1927 0.1528 -0.1086 0.030 Uiso 1 1 calc R . .
H4A H 0.2033 -0.0619 -0.1053 0.030 Uiso 1 1 calc R . .
O5 O -0.11019(5) 0.35846(19) 0.01770(6) 0.0168(3) Uani 1 1 d . . .
C5 C 0.09992(7) 0.1491(2) -0.02808(9) 0.0129(4) Uani 1 1 d . . .
C6 C 0.08848(7) 0.1552(3) -0.09844(9) 0.0147(4) Uani 1 1 d . . .
C7 C 0.09134(8) -0.0077(3) -0.13351(9) 0.0188(4) Uani 1 1 d . . .
H7 H 0.0999(10) -0.124(4) -0.1104(12) 0.029(6) Uiso 1 1 d . . .
C8 C 0.07942(8) -0.0018(3) -0.19903(10) 0.0241(5) Uani 1 1 d . . .
H8 H 0.0821(10) -0.111(4) -0.2209(13) 0.034(7) Uiso 1 1 d . . .
C9 C 0.06535(8) 0.1638(3) -0.22950(10) 0.0255(5) Uani 1 1 d . . .
H9 H 0.0571(10) 0.165(3) -0.2752(12) 0.027(6) Uiso 1 1 d . . .
C10 C 0.06212(8) 0.3258(3) -0.19495(10) 0.0222(4) Uani 1 1 d . . .
H10 H 0.0520(10) 0.440(4) -0.2143(12) 0.029(6) Uiso 1 1 d . . .
C11 C 0.07350(8) 0.3221(3) -0.12926(9) 0.0166(4) Uani 1 1 d . . .
H11 H 0.0728(8) 0.431(3) -0.1054(10) 0.014(5) Uiso 1 1 d . . .
C12 C 0.24004(7) -0.0409(3) 0.14127(9) 0.0160(4) Uani 1 1 d . . .
C13 C 0.29440(8) -0.0395(3) 0.14778(10) 0.0190(4) Uani 1 1 d . . .
H13 H 0.3109(9) 0.005(4) 0.1146(12) 0.028(6) Uiso 1 1 d . . .
C14 C 0.32294(8) -0.0971(3) 0.20410(11) 0.0236(5) Uani 1 1 d . . .
H14 H 0.3597(11) -0.100(4) 0.2074(12) 0.033(7) Uiso 1 1 d . . .
C15 C 0.29837(9) -0.1579(3) 0.25388(11) 0.0248(5) Uani 1 1 d . . .
H15 H 0.3167(10) -0.200(3) 0.2919(12) 0.025(6) Uiso 1 1 d . . .
C16 C 0.24424(9) -0.1596(3) 0.24690(10) 0.0229(5) Uani 1 1 d . . .
H16 H 0.2268(10) -0.200(3) 0.2795(12) 0.030(7) Uiso 1 1 d . . .
C17 C 0.21470(8) -0.1014(3) 0.19082(9) 0.0190(4) Uani 1 1 d . . .
H17 H 0.1784(10) -0.104(3) 0.1867(11) 0.022(6) Uiso 1 1 d . . .
C18 C -0.02060(7) 0.2869(2) 0.01087(9) 0.0136(4) Uani 1 1 d . . .
C19 C -0.07228(7) 0.3338(3) -0.02043(9) 0.0140(4) Uani 1 1 d . . .
C20 C -0.09228(8) 0.3628(3) -0.08212(10) 0.0163(4) Uani 1 1 d . . .
H20 H -0.0758(10) 0.361(4) -0.1169(12) 0.028(7) Uiso 1 1 d . . .
C21 C -0.14572(8) 0.4084(3) -0.08246(10) 0.0187(4) Uani 1 1 d . . .
H21 H -0.1719(10) 0.438(4) -0.1182(12) 0.033(7) Uiso 1 1 d . . .
C22 C -0.15470(8) 0.4020(3) -0.02179(10) 0.0192(4) Uani 1 1 d . . .
H22 H -0.1850(9) 0.414(3) -0.0010(11) 0.022(6) Uiso 1 1 d . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
V1 O2 1.6143(14) . ?
V1 O1 1.6265(14) . ?
V1 O3 1.9387(13) . ?
V1 O4 2.0255(14) . ?
V1 N1 2.1958(16) . ?
N1 C5 1.327(2) . ?
N1 N2 1.398(2) . ?
C1 O3 1.289(2) . ?
C1 N3 1.357(2) . ?
C1 C2 1.415(3) . ?
N2 C18 1.322(2) . ?
N2 H2N 0.84(3) . ?
C2 C5 1.420(3) . ?
C2 C3 1.432(3) . ?
N3 N4 1.393(2) . ?
N3 C12 1.425(2) . ?
C3 N4 1.312(3) . ?
C3 C4 1.500(3) . ?
O4 C18 1.269(2) . ?
C4 H4C 0.9600 . ?
C4 H4B 0.9600 . ?
C4 H4A 0.9600 . ?
O5 C22 1.363(2) . ?
O5 C19 1.372(2) . ?
C5 C6 1.490(3) . ?
C6 C11 1.397(3) . ?
C6 C7 1.398(3) . ?
C7 C8 1.390(3) . ?
C7 H7 0.98(3) . ?
C8 C9 1.380(3) . ?
C8 H8 0.92(3) . ?
C9 C10 1.388(3) . ?
C9 H9 0.97(3) . ?
C10 C11 1.392(3) . ?
C10 H10 0.94(3) . ?
C11 H11 0.94(2) . ?
C12 C17 1.391(3) . ?
C12 C13 1.393(3) . ?
C13 C14 1.383(3) . ?
C13 H13 0.93(3) . ?
C14 C15 1.384(3) . ?
C14 H14 0.94(3) . ?
C15 C16 1.387(3) . ?
C15 H15 0.93(2) . ?
C16 C17 1.391(3) . ?
C16 H16 0.93(3) . ?
C17 H17 0.93(2) . ?
C18 C19 1.447(3) . ?
C19 C20 1.361(3) . ?
C20 C21 1.419(3) . ?
C20 H20 0.91(3) . ?
C21 C22 1.349(3) . ?
C21 H21 0.97(3) . ?
C22 H22 0.96(2) . ?

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 V1 O1 108.92(7) . . ?
O2 V1 O3 96.62(7) . . ?
O1 V1 O3 102.27(6) . . ?
O2 V1 O4 94.24(6) . . ?
O1 V1 O4 97.05(6) . . ?
O3 V1 O4 153.35(6) . . ?
O2 V1 N1 141.83(7) . . ?
O1 V1 N1 108.56(6) . . ?
O3 V1 N1 82.27(6) . . ?
O4 V1 N1 74.23(5) . . ?
C5 N1 N2 115.77(16) . . ?
C5 N1 V1 134.42(13) . . ?
N2 N1 V1 109.45(11) . . ?
O3 C1 N3 122.97(17) . . ?
O3 C1 C2 130.26(17) . . ?
N3 C1 C2 106.66(16) . . ?
C18 N2 N1 114.99(16) . . ?
C18 N2 H2N 121.8(18) . . ?
N1 N2 H2N 121.1(18) . . ?
C1 C2 C5 122.76(17) . . ?
C1 C2 C3 104.59(16) . . ?
C5 C2 C3 132.65(17) . . ?
C1 O3 V1 132.21(12) . . ?
C1 N3 N4 111.05(15) . . ?
C1 N3 C12 129.70(16) . . ?
N4 N3 C12 119.20(15) . . ?
N4 C3 C2 111.14(17) . . ?
N4 C3 C4 118.67(17) . . ?
C2 C3 C4 130.18(17) . . ?
C18 O4 V1 117.76(11) . . ?
C3 N4 N3 106.48(15) . . ?
C3 C4 H4C 109.5 . . ?
C3 C4 H4B 109.5 . . ?
H4C C4 H4B 109.5 . . ?
C3 C4 H4A 109.5 . . ?
H4C C4 H4A 109.5 . . ?
H4B C4 H4A 109.5 . . ?
C22 O5 C19 105.91(15) . . ?
N1 C5 C2 117.42(17) . . ?
N1 C5 C6 121.19(17) . . ?
C2 C5 C6 121.37(16) . . ?
C11 C6 C7 119.97(18) . . ?
C11 C6 C5 120.16(17) . . ?
C7 C6 C5 119.85(17) . . ?
C8 C7 C6 119.51(19) . . ?
C8 C7 H7 122.5(15) . . ?
C6 C7 H7 118.0(15) . . ?
C9 C8 C7 120.5(2) . . ?
C9 C8 H8 121.9(17) . . ?
C7 C8 H8 117.6(17) . . ?
C8 C9 C10 120.3(2) . . ?
C8 C9 H9 119.1(14) . . ?
C10 C9 H9 120.6(14) . . ?
C9 C10 C11 120.0(2) . . ?
C9 C10 H10 122.3(15) . . ?
C11 C10 H10 117.7(15) . . ?
C10 C11 C6 119.74(19) . . ?
C10 C11 H11 120.9(13) . . ?
C6 C11 H11 119.3(13) . . ?
C17 C12 C13 120.27(18) . . ?
C17 C12 N3 120.63(17) . . ?
C13 C12 N3 119.07(18) . . ?
C14 C13 C12 119.4(2) . . ?
C14 C13 H13 121.1(15) . . ?
C12 C13 H13 119.4(15) . . ?
C13 C14 C15 121.1(2) . . ?
C13 C14 H14 118.6(16) . . ?
C15 C14 H14 120.3(16) . . ?
C14 C15 C16 119.1(2) . . ?
C14 C15 H15 122.7(15) . . ?
C16 C15 H15 118.1(15) . . ?
C15 C16 C17 120.8(2) . . ?
C15 C16 H16 121.0(16) . . ?
C17 C16 H16 118.2(16) . . ?
C16 C17 C12 119.26(19) . . ?
C16 C17 H17 119.8(14) . . ?
C12 C17 H17 120.9(14) . . ?
O4 C18 N2 119.93(17) . . ?
O4 C18 C19 122.59(17) . . ?
N2 C18 C19 117.46(17) . . ?
C20 C19 O5 110.44(16) . . ?
C20 C19 C18 133.01(18) . . ?
O5 C19 C18 116.54(16) . . ?
C19 C20 C21 106.05(18) . . ?
C19 C20 H20 129.1(16) . . ?
C21 C20 H20 124.8(16) . . ?
C22 C21 C20 106.69(18) . . ?
C22 C21 H21 124.6(15) . . ?
C20 C21 H21 128.7(15) . . ?
C21 C22 O5 110.90(17) . . ?
C21 C22 H22 134.9(14) . . ?
O5 C22 H22 114.1(14) . . ?

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
O2 V1 N1 C5 95.88(19) . . . . ?
O1 V1 N1 C5 -95.43(18) . . . . ?
O3 V1 N1 C5 4.98(18) . . . . ?
O4 V1 N1 C5 172.30(19) . . . . ?
O2 V1 N1 N2 -91.53(15) . . . . ?
O1 V1 N1 N2 77.17(12) . . . . ?
O3 V1 N1 N2 177.57(12) . . . . ?
O4 V1 N1 N2 -15.11(11) . . . . ?
C5 N1 N2 C18 -172.92(16) . . . . ?
V1 N1 N2 C18 12.95(19) . . . . ?
O3 C1 C2 C5 -6.6(3) . . . . ?
N3 C1 C2 C5 177.03(17) . . . . ?
O3 C1 C2 C3 173.61(19) . . . . ?
N3 C1 C2 C3 -2.7(2) . . . . ?
N3 C1 O3 V1 -173.25(13) . . . . ?
C2 C1 O3 V1 10.9(3) . . . . ?
O2 V1 O3 C1 -149.43(17) . . . . ?
O1 V1 O3 C1 99.51(17) . . . . ?
O4 V1 O3 C1 -36.0(2) . . . . ?
N1 V1 O3 C1 -7.89(17) . . . . ?
O3 C1 N3 N4 -173.91(17) . . . . ?
C2 C1 N3 N4 2.8(2) . . . . ?
O3 C1 N3 C12 8.7(3) . . . . ?
C2 C1 N3 C12 -174.65(18) . . . . ?
C1 C2 C3 N4 1.9(2) . . . . ?
C5 C2 C3 N4 -177.86(19) . . . . ?
C1 C2 C3 C4 -176.8(2) . . . . ?
C5 C2 C3 C4 3.5(4) . . . . ?
O2 V1 O4 C18 159.67(13) . . . . ?
O1 V1 O4 C18 -90.64(13) . . . . ?
O3 V1 O4 C18 45.7(2) . . . . ?
N1 V1 O4 C18 16.71(13) . . . . ?
C2 C3 N4 N3 -0.2(2) . . . . ?
C4 C3 N4 N3 178.60(16) . . . . ?
C1 N3 N4 C3 -1.6(2) . . . . ?
C12 N3 N4 C3 176.11(16) . . . . ?
N2 N1 C5 C2 -175.90(15) . . . . ?
V1 N1 C5 C2 -3.7(3) . . . . ?
N2 N1 C5 C6 2.3(2) . . . . ?
V1 N1 C5 C6 174.50(13) . . . . ?
C1 C2 C5 N1 2.9(3) . . . . ?
C3 C2 C5 N1 -177.46(19) . . . . ?
C1 C2 C5 C6 -175.29(17) . . . . ?
C3 C2 C5 C6 4.4(3) . . . . ?
N1 C5 C6 C11 62.2(2) . . . . ?
C2 C5 C6 C11 -119.7(2) . . . . ?
N1 C5 C6 C7 -116.0(2) . . . . ?
C2 C5 C6 C7 62.1(2) . . . . ?
C11 C6 C7 C8 0.3(3) . . . . ?
C5 C6 C7 C8 178.50(18) . . . . ?
C6 C7 C8 C9 0.6(3) . . . . ?
C7 C8 C9 C10 -1.1(3) . . . . ?
C8 C9 C10 C11 0.5(3) . . . . ?
C9 C10 C11 C6 0.4(3) . . . . ?
C7 C6 C11 C10 -0.8(3) . . . . ?
C5 C6 C11 C10 -179.02(18) . . . . ?
C1 N3 C12 C17 22.9(3) . . . . ?
N4 N3 C12 C17 -154.36(18) . . . . ?
C1 N3 C12 C13 -159.06(19) . . . . ?
N4 N3 C12 C13 23.7(3) . . . . ?
C17 C12 C13 C14 -0.6(3) . . . . ?
N3 C12 C13 C14 -178.65(18) . . . . ?
C12 C13 C14 C15 0.6(3) . . . . ?
C13 C14 C15 C16 -0.3(3) . . . . ?
C14 C15 C16 C17 0.0(3) . . . . ?
C15 C16 C17 C12 0.0(3) . . . . ?
C13 C12 C17 C16 0.3(3) . . . . ?
N3 C12 C17 C16 178.30(18) . . . . ?
V1 O4 C18 N2 -15.6(2) . . . . ?
V1 O4 C18 C19 166.04(13) . . . . ?
N1 N2 C18 O4 0.4(2) . . . . ?
N1 N2 C18 C19 178.82(15) . . . . ?
C22 O5 C19 C20 0.6(2) . . . . ?
C22 O5 C19 C18 179.68(16) . . . . ?
O4 C18 C19 C20 164.7(2) . . . . ?
N2 C18 C19 C20 -13.7(3) . . . . ?
O4 C18 C19 O5 -14.1(3) . . . . ?
N2 C18 C19 O5 167.49(16) . . . . ?
O5 C19 C20 C21 0.1(2) . . . . ?
C18 C19 C20 C21 -178.8(2) . . . . ?
C19 C20 C21 C22 -0.7(2) . . . . ?
C20 C21 C22 O5 1.1(2) . . . . ?
C19 O5 C22 C21 -1.1(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
N2 H2N O1 0.84(3) 1.99(3) 2.770(2) 153(2) 5

_diffrn_measured_fraction_theta_max 0.993
_diffrn_reflns_theta_full        26.38
_diffrn_measured_fraction_theta_full 0.993
_refine_diff_density_max         0.370
_refine_diff_density_min         -0.406
_refine_diff_density_rms         0.082
####################################################################### 
# 
# 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_compound9
_database_code_depnum_ccdc_archive 'CCDC 1502027'
_audit_update_record             
;
2016-09-01 deposited with the CCDC.
2016-09-15 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C23 H18 N5 O4 V'
_chemical_formula_sum            'C23 H18 N5 O4 V'
_chemical_formula_weight         479.36

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

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   P-1
_symmetry_space_group_name_Hall  -P1

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

_cell_length_a                   9.0595(8)
_cell_length_b                   9.6948(9)
_cell_length_c                   12.4414(13)
_cell_angle_alpha                95.526(6)
_cell_angle_beta                 98.606(6)
_cell_angle_gamma                94.410(6)
_cell_volume                     1070.77(18)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    19128
_cell_measurement_theta_min      5.208
_cell_measurement_theta_max      44.833

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.06
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.487
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             492
_exptl_absorpt_coefficient_mu    0.505
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8987
_exptl_absorpt_correction_T_max  0.9698
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            29571
_diffrn_reflns_av_R_equivalents  0.0711
_diffrn_reflns_av_unetI/netI     0.0517
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         1.67
_diffrn_reflns_theta_max         26.41
_reflns_number_total             4374
_reflns_number_gt                3140
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Apex2, Bruker Instrument Service v2010, 1-2'
_computing_cell_refinement       
'SAINT V7.68A (Bruker: Madison, 2009 ) in Apex2 suite'
_computing_data_reduction        
'SAINT and XPREP Version 2008/2 (Sheldrick, Bruker AXS Inc.)'
_computing_structure_solution    
'XS V2008/1 (G. M. Sheldrick, Acta Cryst. (2008). A64, 112-122)'
_computing_structure_refinement  
'XL V2008/4 (G. M. Sheldrick, Acta Cryst. (2008). A64, 112-122)'
_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)+(0.0762P)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    mixed
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.036(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         4374
_refine_ls_number_parameters     360
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0746
_refine_ls_R_factor_gt           0.0457
_refine_ls_wR_factor_ref         0.1318
_refine_ls_wR_factor_gt          0.1125
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_restrained_S_all      1.055
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
V1 V 0.31436(5) 0.13452(5) 0.40834(4) 0.02498(18) Uani 1 1 d . . .
C1 C 0.1938(3) -0.1097(3) 0.2527(2) 0.0243(6) Uani 1 1 d . . .
O1 O 0.2638(2) 0.08650(19) 0.51941(16) 0.0305(5) Uani 1 1 d . . .
N1 N 0.1052(2) 0.1582(2) 0.30392(18) 0.0247(5) Uani 1 1 d . . .
O2 O 0.4967(2) 0.15983(19) 0.42297(17) 0.0320(5) Uani 1 1 d . . .
C2 C 0.0514(3) -0.0702(3) 0.2151(2) 0.0252(6) Uani 1 1 d . . .
N2 N 0.0556(2) 0.2919(2) 0.31786(19) 0.0257(5) Uani 1 1 d . . .
N3 N 0.1974(2) -0.2441(2) 0.21008(19) 0.0255(5) Uani 1 1 d . . .
O3 O 0.3065(2) -0.03811(19) 0.31387(15) 0.0268(4) Uani 1 1 d . . .
C3 C -0.0246(3) -0.1916(3) 0.1475(2) 0.0269(6) Uani 1 1 d . . .
N4 N 0.0620(3) -0.2941(2) 0.1452(2) 0.0296(6) Uani 1 1 d . . .
O4 O 0.2902(2) 0.33341(19) 0.42296(16) 0.0274(4) Uani 1 1 d . . .
C4 C -0.1786(3) -0.2155(3) 0.0816(3) 0.0384(8) Uani 1 1 d . . .
H4A H -0.1909 -0.3058 0.0406 0.058 Uiso 1 1 calc R . .
H4B H -0.1917 -0.1456 0.0323 0.058 Uiso 1 1 calc R . .
H4C H -0.2519 -0.2104 0.1298 0.058 Uiso 1 1 calc R . .
N5 N 0.2280(3) 0.7413(2) 0.49780(19) 0.0262(5) Uani 1 1 d . . .
H5N H 0.321(4) 0.800(3) 0.538(3) 0.043(9) Uiso 1 1 d . . .
C5 C 0.0091(3) 0.0663(3) 0.2389(2) 0.0241(6) Uani 1 1 d . . .
C6 C -0.1410(3) 0.1025(3) 0.1888(2) 0.0248(6) Uani 1 1 d . . .
C7 C -0.2683(3) 0.0528(3) 0.2277(2) 0.0293(7) Uani 1 1 d . . .
H7 H -0.260(3) 0.001(3) 0.289(2) 0.022(7) Uiso 1 1 d . . .
C8 C -0.4088(3) 0.0766(3) 0.1755(3) 0.0335(7) Uani 1 1 d . . .
H8 H -0.487(4) 0.043(3) 0.201(3) 0.039(9) Uiso 1 1 d . . .
C9 C -0.4225(4) 0.1489(3) 0.0849(3) 0.0378(8) Uani 1 1 d . . .
H9 H -0.509(4) 0.162(3) 0.049(3) 0.040(9) Uiso 1 1 d . . .
C10 C -0.2957(4) 0.2010(3) 0.0475(3) 0.0381(8) Uani 1 1 d . . .
H10 H -0.311(4) 0.253(4) -0.016(3) 0.046(9) Uiso 1 1 d . . .
C11 C -0.1553(3) 0.1783(3) 0.0995(2) 0.0318(7) Uani 1 1 d . . .
H11 H -0.076(4) 0.217(3) 0.075(3) 0.037(9) Uiso 1 1 d . . .
C12 C 0.1608(3) 0.3727(3) 0.3808(2) 0.0248(6) Uani 1 1 d . . .
C13 C 0.1354(3) 0.5196(3) 0.4078(2) 0.0239(6) Uani 1 1 d . . .
C14 C 0.0004(3) 0.5736(3) 0.3719(2) 0.0266(6) Uani 1 1 d . . .
H14 H -0.077(3) 0.514(3) 0.326(2) 0.030(8) Uiso 1 1 d . . .
C15 C -0.0191(3) 0.7102(3) 0.4039(2) 0.0277(6) Uani 1 1 d . . .
H15 H -0.107(3) 0.751(3) 0.380(2) 0.024(7) Uiso 1 1 d . . .
C16 C 0.0974(3) 0.7936(3) 0.4675(2) 0.0274(6) Uani 1 1 d . . .
H16 H 0.097(3) 0.888(3) 0.493(2) 0.021(7) Uiso 1 1 d . . .
C17 C 0.2492(3) 0.6081(3) 0.4710(2) 0.0254(6) Uani 1 1 d . . .
H17 H 0.341(3) 0.577(3) 0.491(2) 0.034(8) Uiso 1 1 d . . .
C18 C 0.3140(3) -0.3354(3) 0.2232(2) 0.0255(6) Uani 1 1 d . . .
C19 C 0.4504(3) -0.2939(3) 0.2890(2) 0.0288(6) Uani 1 1 d . . .
H19 H 0.470(3) -0.209(3) 0.327(2) 0.023(7) Uiso 1 1 d . . .
C20 C 0.5573(3) -0.3895(3) 0.3018(3) 0.0344(7) Uani 1 1 d . . .
H20 H 0.642(4) -0.368(3) 0.344(3) 0.035(9) Uiso 1 1 d . . .
C21 C 0.5296(4) -0.5233(3) 0.2504(3) 0.0390(8) Uani 1 1 d . . .
H21 H 0.598(4) -0.587(3) 0.259(3) 0.037(9) Uiso 1 1 d . . .
C22 C 0.3916(4) -0.5628(3) 0.1855(3) 0.0403(8) Uani 1 1 d . . .
H22 H 0.377(4) -0.659(4) 0.147(3) 0.056(10) Uiso 1 1 d . . .
C23 C 0.2851(4) -0.4699(3) 0.1713(3) 0.0348(7) Uani 1 1 d . . .
H23 H 0.200(4) -0.493(4) 0.136(3) 0.046(10) Uiso 1 1 d . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
V1 O1 1.618(2) . ?
V1 O2 1.6317(19) . ?
V1 O3 1.9404(18) . ?
V1 O4 1.9514(19) . ?
V1 N1 2.172(2) . ?
C1 O3 1.289(3) . ?
C1 N3 1.364(3) . ?
C1 C2 1.400(4) . ?
N1 C5 1.318(3) . ?
N1 N2 1.408(3) . ?
C2 C5 1.421(4) . ?
C2 C3 1.442(4) . ?
N2 C12 1.296(3) . ?
N3 N4 1.389(3) . ?
N3 C18 1.430(3) . ?
C3 N4 1.314(3) . ?
C3 C4 1.498(4) . ?
O4 C12 1.310(3) . ?
C4 H4A 0.9600 . ?
C4 H4B 0.9600 . ?
C4 H4C 0.9600 . ?
N5 C17 1.338(4) . ?
N5 C16 1.340(3) . ?
N5 H5N 1.02(3) . ?
C5 C6 1.491(4) . ?
C6 C11 1.386(4) . ?
C6 C7 1.386(4) . ?
C7 C8 1.387(4) . ?
C7 H7 0.95(3) . ?
C8 C9 1.379(5) . ?
C8 H8 0.88(3) . ?
C9 C10 1.381(5) . ?
C9 H9 0.87(3) . ?
C10 C11 1.382(4) . ?
C10 H10 0.97(3) . ?
C11 H11 0.89(3) . ?
C12 C13 1.475(4) . ?
C13 C17 1.382(4) . ?
C13 C14 1.396(4) . ?
C14 C15 1.378(4) . ?
C14 H14 0.95(3) . ?
C15 C16 1.375(4) . ?
C15 H15 0.94(3) . ?
C16 H16 0.94(3) . ?
C17 H17 0.92(3) . ?
C18 C19 1.384(4) . ?
C18 C23 1.386(4) . ?
C19 C20 1.394(4) . ?
C19 H19 0.90(3) . ?
C20 C21 1.377(4) . ?
C20 H20 0.86(3) . ?
C21 C22 1.388(4) . ?
C21 H21 0.91(3) . ?
C22 C23 1.373(4) . ?
C22 H22 1.00(4) . ?
C23 H23 0.83(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 V1 O2 110.05(10) . . ?
O1 V1 O3 104.20(9) . . ?
O2 V1 O3 93.23(9) . . ?
O1 V1 O4 102.38(9) . . ?
O2 V1 O4 93.13(9) . . ?
O3 V1 O4 148.60(8) . . ?
O1 V1 N1 104.50(9) . . ?
O2 V1 N1 145.05(10) . . ?
O3 V1 N1 83.12(8) . . ?
O4 V1 N1 74.24(8) . . ?
O3 C1 N3 123.3(2) . . ?
O3 C1 C2 129.5(2) . . ?
N3 C1 C2 107.2(2) . . ?
C5 N1 N2 114.3(2) . . ?
C5 N1 V1 131.32(18) . . ?
N2 N1 V1 113.93(15) . . ?
C1 C2 C5 123.0(2) . . ?
C1 C2 C3 104.4(2) . . ?
C5 C2 C3 132.5(2) . . ?
C12 N2 N1 108.3(2) . . ?
C1 N3 N4 111.0(2) . . ?
C1 N3 C18 130.6(2) . . ?
N4 N3 C18 118.4(2) . . ?
C1 O3 V1 129.91(17) . . ?
N4 C3 C2 111.2(2) . . ?
N4 C3 C4 118.0(2) . . ?
C2 C3 C4 130.8(2) . . ?
C3 N4 N3 106.3(2) . . ?
C12 O4 V1 117.54(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 . . ?
C17 N5 C16 122.4(2) . . ?
C17 N5 H5N 114.1(18) . . ?
C16 N5 H5N 123.4(18) . . ?
N1 C5 C2 118.7(2) . . ?
N1 C5 C6 121.7(2) . . ?
C2 C5 C6 119.5(2) . . ?
C11 C6 C7 119.6(3) . . ?
C11 C6 C5 120.6(3) . . ?
C7 C6 C5 119.7(3) . . ?
C6 C7 C8 119.8(3) . . ?
C6 C7 H7 120.6(16) . . ?
C8 C7 H7 119.5(16) . . ?
C9 C8 C7 120.3(3) . . ?
C9 C8 H8 122(2) . . ?
C7 C8 H8 118(2) . . ?
C8 C9 C10 119.9(3) . . ?
C8 C9 H9 122(2) . . ?
C10 C9 H9 118(2) . . ?
C9 C10 C11 120.0(3) . . ?
C9 C10 H10 117(2) . . ?
C11 C10 H10 123(2) . . ?
C10 C11 C6 120.3(3) . . ?
C10 C11 H11 117(2) . . ?
C6 C11 H11 122(2) . . ?
N2 C12 O4 124.6(2) . . ?
N2 C12 C13 118.6(2) . . ?
O4 C12 C13 116.8(2) . . ?
C17 C13 C14 118.3(3) . . ?
C17 C13 C12 119.1(2) . . ?
C14 C13 C12 122.6(2) . . ?
C15 C14 C13 120.0(3) . . ?
C15 C14 H14 121.6(18) . . ?
C13 C14 H14 118.4(18) . . ?
C16 C15 C14 119.3(3) . . ?
C16 C15 H15 117.6(17) . . ?
C14 C15 H15 122.9(17) . . ?
N5 C16 C15 119.8(3) . . ?
N5 C16 H16 113.7(16) . . ?
C15 C16 H16 126.5(16) . . ?
N5 C17 C13 120.1(3) . . ?
N5 C17 H17 120(2) . . ?
C13 C17 H17 119.8(19) . . ?
C19 C18 C23 120.2(3) . . ?
C19 C18 N3 121.6(2) . . ?
C23 C18 N3 118.2(2) . . ?
C18 C19 C20 118.8(3) . . ?
C18 C19 H19 122.2(17) . . ?
C20 C19 H19 118.9(17) . . ?
C21 C20 C19 121.3(3) . . ?
C21 C20 H20 118(2) . . ?
C19 C20 H20 121(2) . . ?
C20 C21 C22 118.8(3) . . ?
C20 C21 H21 122(2) . . ?
C22 C21 H21 119(2) . . ?
C23 C22 C21 120.8(3) . . ?
C23 C22 H22 122(2) . . ?
C21 C22 H22 117(2) . . ?
C22 C23 C18 120.1(3) . . ?
C22 C23 H23 122(2) . . ?
C18 C23 H23 118(2) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 V1 N1 C5 -82.9(3) . . . . ?
O2 V1 N1 C5 105.8(3) . . . . ?
O3 V1 N1 C5 20.0(2) . . . . ?
O4 V1 N1 C5 178.0(3) . . . . ?
O1 V1 N1 N2 88.79(18) . . . . ?
O2 V1 N1 N2 -82.5(2) . . . . ?
O3 V1 N1 N2 -168.27(18) . . . . ?
O4 V1 N1 N2 -10.24(16) . . . . ?
O3 C1 C2 C5 1.8(5) . . . . ?
N3 C1 C2 C5 -176.9(2) . . . . ?
O3 C1 C2 C3 178.1(3) . . . . ?
N3 C1 C2 C3 -0.5(3) . . . . ?
C5 N1 N2 C12 -178.4(2) . . . . ?
V1 N1 N2 C12 8.5(3) . . . . ?
O3 C1 N3 N4 -178.5(2) . . . . ?
C2 C1 N3 N4 0.3(3) . . . . ?
O3 C1 N3 C18 2.2(5) . . . . ?
C2 C1 N3 C18 -179.0(3) . . . . ?
N3 C1 O3 V1 -164.42(19) . . . . ?
C2 C1 O3 V1 17.1(4) . . . . ?
O1 V1 O3 C1 81.7(2) . . . . ?
O2 V1 O3 C1 -166.6(2) . . . . ?
O4 V1 O3 C1 -65.3(3) . . . . ?
N1 V1 O3 C1 -21.5(2) . . . . ?
C1 C2 C3 N4 0.6(3) . . . . ?
C5 C2 C3 N4 176.5(3) . . . . ?
C1 C2 C3 C4 -178.4(3) . . . . ?
C5 C2 C3 C4 -2.5(5) . . . . ?
C2 C3 N4 N3 -0.5(3) . . . . ?
C4 C3 N4 N3 178.7(3) . . . . ?
C1 N3 N4 C3 0.1(3) . . . . ?
C18 N3 N4 C3 179.5(2) . . . . ?
O1 V1 O4 C12 -91.7(2) . . . . ?
O2 V1 O4 C12 157.0(2) . . . . ?
O3 V1 O4 C12 55.6(3) . . . . ?
N1 V1 O4 C12 10.15(18) . . . . ?
N2 N1 C5 C2 177.0(2) . . . . ?
V1 N1 C5 C2 -11.3(4) . . . . ?
N2 N1 C5 C6 -2.2(4) . . . . ?
V1 N1 C5 C6 169.46(19) . . . . ?
C1 C2 C5 N1 -3.7(4) . . . . ?
C3 C2 C5 N1 -178.9(3) . . . . ?
C1 C2 C5 C6 175.5(3) . . . . ?
C3 C2 C5 C6 0.3(5) . . . . ?
N1 C5 C6 C11 77.5(4) . . . . ?
C2 C5 C6 C11 -101.7(3) . . . . ?
N1 C5 C6 C7 -106.4(3) . . . . ?
C2 C5 C6 C7 74.4(3) . . . . ?
C11 C6 C7 C8 1.5(4) . . . . ?
C5 C6 C7 C8 -174.6(3) . . . . ?
C6 C7 C8 C9 0.2(4) . . . . ?
C7 C8 C9 C10 -1.6(5) . . . . ?
C8 C9 C10 C11 1.3(5) . . . . ?
C9 C10 C11 C6 0.5(5) . . . . ?
C7 C6 C11 C10 -1.9(4) . . . . ?
C5 C6 C11 C10 174.3(3) . . . . ?
N1 N2 C12 O4 0.0(4) . . . . ?
N1 N2 C12 C13 -180.0(2) . . . . ?
V1 O4 C12 N2 -9.7(4) . . . . ?
V1 O4 C12 C13 170.28(18) . . . . ?
N2 C12 C13 C17 -177.3(2) . . . . ?
O4 C12 C13 C17 2.8(4) . . . . ?
N2 C12 C13 C14 2.6(4) . . . . ?
O4 C12 C13 C14 -177.4(2) . . . . ?
C17 C13 C14 C15 -3.1(4) . . . . ?
C12 C13 C14 C15 177.1(3) . . . . ?
C13 C14 C15 C16 2.7(4) . . . . ?
C17 N5 C16 C15 -2.0(4) . . . . ?
C14 C15 C16 N5 -0.2(4) . . . . ?
C16 N5 C17 C13 1.5(4) . . . . ?
C14 C13 C17 N5 1.0(4) . . . . ?
C12 C13 C17 N5 -179.1(2) . . . . ?
C1 N3 C18 C19 1.0(5) . . . . ?
N4 N3 C18 C19 -178.3(3) . . . . ?
C1 N3 C18 C23 178.6(3) . . . . ?
N4 N3 C18 C23 -0.7(4) . . . . ?
C23 C18 C19 C20 0.0(5) . . . . ?
N3 C18 C19 C20 177.5(3) . . . . ?
C18 C19 C20 C21 0.1(5) . . . . ?
C19 C20 C21 C22 -0.5(5) . . . . ?
C20 C21 C22 C23 0.9(5) . . . . ?
C21 C22 C23 C18 -0.9(5) . . . . ?
C19 C18 C23 C22 0.4(5) . . . . ?
N3 C18 C23 C22 -177.2(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
N5 H5N O2 1.02(3) 1.65(3) 2.612(3) 155(3) 2_666

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        26.41
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         0.501
_refine_diff_density_min         -0.507
_refine_diff_density_rms         0.163
####################################################################### 
# 
# 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_compound10
_database_code_depnum_ccdc_archive 'CCDC 1502028'
_audit_update_record             
;
2016-09-01 deposited with the CCDC.
2016-09-15 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C25 H24 N5 O5 S V'
_chemical_formula_sum            'C25 H24 N5 O5 S V'
_chemical_formula_weight         557.49

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'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   P-1
_symmetry_space_group_name_Hall  -P1


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

_cell_length_a                   8.2826(7)
_cell_length_b                   11.0071(9)
_cell_length_c                   14.2227(12)
_cell_angle_alpha                87.501(5)
_cell_angle_beta                 81.094(5)
_cell_angle_gamma                82.501(4)
_cell_volume                     1269.69(18)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    47457
_cell_measurement_theta_min      4.672
_cell_measurement_theta_max      49.826

_exptl_crystal_description       needle
_exptl_crystal_colour            orange
_exptl_crystal_size_max          0.49
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.12
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.458
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             576
_exptl_absorpt_coefficient_mu    0.519
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7850
_exptl_absorpt_correction_T_max  0.9418
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            47446
_diffrn_reflns_av_R_equivalents  0.0378
_diffrn_reflns_av_unetI/netI     0.0201
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         1.45
_diffrn_reflns_theta_max         26.42
_reflns_number_total             5202
_reflns_number_gt                4556
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Apex2, Bruker Instrument Service v2010, 1-2'
_computing_cell_refinement       
'SAINT V7.68A (Bruker: Madison, 2009 ) in Apex2 suite'
_computing_data_reduction        
'SAINT and XPREP Version 2008/2 (Sheldrick, Bruker AXS Inc.)'
_computing_structure_solution    
'XS V2008/1 (G. M. Sheldrick, Acta Cryst. (2008). A64, 112-122)'
_computing_structure_refinement  
'XL V2008/4 (G. M. Sheldrick, Acta Cryst. (2008). A64, 112-122)'
_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)+(0.0657P)²+0.3715P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         5202
_refine_ls_number_parameters     397
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0408
_refine_ls_R_factor_gt           0.0331
_refine_ls_wR_factor_ref         0.1128
_refine_ls_wR_factor_gt          0.0985
_refine_ls_goodness_of_fit_ref   1.109
_refine_ls_restrained_S_all      1.109
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
V1 V 0.26167(4) 0.54935(3) 0.31333(2) 0.02714(11) Uani 1 1 d . . .
O1 O 0.12353(19) 0.56787(14) 0.40681(11) 0.0434(4) Uani 1 1 d . . .
N1 N 0.2935(2) 0.73596(14) 0.26349(11) 0.0290(3) Uani 1 1 d . . .
C1 C 0.0466(2) 0.64729(17) 0.17987(14) 0.0311(4) Uani 1 1 d . . .
S1 S 0.27423(7) 0.74346(5) 0.57233(4) 0.04348(16) Uani 1 1 d . . .
C1S C 0.1894(4) 0.6352(3) 0.6537(2) 0.0692(8) Uani 1 1 d . . .
H1S1 H 0.1240 0.6776 0.7088 0.104 Uiso 1 1 calc R . .
H1S2 H 0.2784 0.5780 0.6747 0.104 Uiso 1 1 calc R . .
H1S3 H 0.1187 0.5899 0.6228 0.104 Uiso 1 1 calc R . .
O2 O 0.32916(18) 0.40430(12) 0.30579(11) 0.0369(3) Uani 1 1 d . . .
N2 N 0.4235(2) 0.78331(14) 0.29390(12) 0.0311(4) Uani 1 1 d . . .
C2 C 0.0651(2) 0.77177(17) 0.18187(14) 0.0304(4) Uani 1 1 d . . .
C2S C 0.3899(4) 0.8098(3) 0.6462(3) 0.0761(10) Uani 1 1 d . . .
H2S1 H 0.4408 0.8774 0.6116 0.114 Uiso 1 1 calc R . .
H2S2 H 0.4761 0.7477 0.6647 0.114 Uiso 1 1 calc R . .
H2S3 H 0.3172 0.8410 0.7034 0.114 Uiso 1 1 calc R . .
O3 O 0.13780(18) 0.55194(12) 0.20748(11) 0.0366(3) Uani 1 1 d . . .
N3 N -0.0925(2) 0.64106(15) 0.14139(12) 0.0335(4) Uani 1 1 d . . .
C3 C -0.0746(2) 0.83446(18) 0.14457(14) 0.0327(4) Uani 1 1 d . . .
O4 O 0.46343(17) 0.58724(12) 0.35660(10) 0.0336(3) Uani 1 1 d . . .
N4 N -0.1687(2) 0.75712(16) 0.12129(12) 0.0360(4) Uani 1 1 d . . .
C4 C -0.1275(3) 0.96918(19) 0.13438(17) 0.0430(5) Uani 1 1 d . . .
H4A H -0.0612 1.0023 0.0784 0.064 Uiso 1 1 calc R . .
H4B H -0.1119 1.0104 0.1914 0.064 Uiso 1 1 calc R . .
H4C H -0.2441 0.9829 0.1267 0.064 Uiso 1 1 calc R . .
N5 N 0.8843(2) 0.79640(16) 0.47302(13) 0.0352(4) Uani 1 1 d . . .
H5N H 0.961(3) 0.812(2) 0.4983(17) 0.040(7) Uiso 1 1 d . . .
C5 C 0.1992(2) 0.81422(17) 0.21640(13) 0.0289(4) Uani 1 1 d . . .
C6 C 0.2324(2) 0.94333(17) 0.19795(14) 0.0313(4) Uani 1 1 d . . .
C7 C 0.2798(3) 0.9837(2) 0.10558(17) 0.0455(5) Uani 1 1 d . . .
H7 H 0.299(3) 0.924(2) 0.0563(18) 0.047(7) Uiso 1 1 d . . .
O7 O 0.1323(2) 0.84226(15) 0.55924(13) 0.0501(4) Uani 1 1 d . . .
C8 C 0.3075(4) 1.1047(2) 0.0873(2) 0.0567(7) Uani 1 1 d . . .
H8 H 0.333(4) 1.126(3) 0.026(2) 0.070(9) Uiso 1 1 d . . .
C9 C 0.2863(3) 1.1848(2) 0.1611(2) 0.0528(6) Uani 1 1 d . . .
H9 H 0.299(3) 1.268(3) 0.153(2) 0.058(8) Uiso 1 1 d . . .
C10 C 0.2385(3) 1.1453(2) 0.2524(2) 0.0510(6) Uani 1 1 d . . .
H10 H 0.229(3) 1.199(3) 0.301(2) 0.059(8) Uiso 1 1 d . . .
C11 C 0.2122(3) 1.0250(2) 0.27209(17) 0.0409(5) Uani 1 1 d . . .
H11 H 0.187(3) 0.997(2) 0.3344(19) 0.048(7) Uiso 1 1 d . . .
C12 C 0.4994(2) 0.69866(17) 0.34326(13) 0.0288(4) Uani 1 1 d . . .
C13 C 0.6355(2) 0.73305(17) 0.38812(13) 0.0287(4) Uani 1 1 d . . .
C14 C 0.6988(3) 0.84320(19) 0.36413(16) 0.0383(5) Uani 1 1 d . . .
H14 H 0.656(3) 0.892(2) 0.3180(19) 0.051(7) Uiso 1 1 d . . .
C15 C 0.8228(3) 0.8733(2) 0.40775(18) 0.0417(5) Uani 1 1 d . . .
H15 H 0.871(3) 0.942(2) 0.3940(18) 0.045(7) Uiso 1 1 d . . .
C16 C 0.8270(2) 0.69033(19) 0.49731(15) 0.0332(4) Uani 1 1 d . . .
H16 H 0.876(3) 0.643(2) 0.5424(17) 0.039(6) Uiso 1 1 d . . .
C17 C 0.7014(2) 0.65673(19) 0.45605(15) 0.0321(4) Uani 1 1 d . . .
H17 H 0.662(3) 0.589(2) 0.4745(17) 0.040(6) Uiso 1 1 d . . .
C18 C -0.1640(3) 0.53633(19) 0.12088(14) 0.0337(4) Uani 1 1 d . . .
C19 C -0.0666(3) 0.4263(2) 0.10000(16) 0.0399(5) Uani 1 1 d . . .
H19 H 0.042(3) 0.419(2) 0.1013(18) 0.046(7) Uiso 1 1 d . . .
C20 C -0.1387(4) 0.3262(2) 0.07881(18) 0.0506(6) Uani 1 1 d . . .
H20 H -0.070(3) 0.250(3) 0.066(2) 0.060(8) Uiso 1 1 d . . .
C21 C -0.3063(4) 0.3366(3) 0.0790(2) 0.0592(7) Uani 1 1 d . . .
H21 H -0.358(4) 0.270(3) 0.065(2) 0.064(8) Uiso 1 1 d . . .
C22 C -0.4021(3) 0.4466(3) 0.09897(19) 0.0554(7) Uani 1 1 d . . .
H22 H -0.517(4) 0.463(3) 0.094(2) 0.070(9) Uiso 1 1 d . . .
C23 C -0.3325(3) 0.5480(2) 0.12000(16) 0.0433(5) Uani 1 1 d . . .
H23 H -0.394(3) 0.625(2) 0.1323(17) 0.040(6) Uiso 1 1 d . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
V1 O1 1.6156(15) . ?
V1 O2 1.6238(13) . ?
V1 O3 1.9460(14) . ?
V1 O4 1.9666(14) . ?
V1 N1 2.1789(15) . ?
N1 C5 1.318(2) . ?
N1 N2 1.388(2) . ?
C1 O3 1.294(2) . ?
C1 N3 1.361(2) . ?
C1 C2 1.400(3) . ?
S1 O7 1.5219(16) . ?
S1 C1S 1.760(3) . ?
S1 C2S 1.766(3) . ?
C1S H1S1 0.9800 . ?
C1S H1S2 0.9800 . ?
C1S H1S3 0.9800 . ?
N2 C12 1.297(2) . ?
C2 C5 1.420(3) . ?
C2 C3 1.431(3) . ?
C2S H2S1 0.9800 . ?
C2S H2S2 0.9800 . ?
C2S H2S3 0.9800 . ?
N3 N4 1.388(2) . ?
N3 C18 1.423(3) . ?
C3 N4 1.311(3) . ?
C3 C4 1.498(3) . ?
O4 C12 1.299(2) . ?
C4 H4A 0.9800 . ?
C4 H4B 0.9800 . ?
C4 H4C 0.9800 . ?
N5 C16 1.329(3) . ?
N5 C15 1.343(3) . ?
N5 H5N 0.82(3) . ?
C5 C6 1.487(3) . ?
C6 C7 1.383(3) . ?
C6 C11 1.392(3) . ?
C7 C8 1.388(3) . ?
C7 H7 0.96(3) . ?
C8 C9 1.376(4) . ?
C8 H8 0.90(3) . ?
C9 C10 1.367(4) . ?
C9 H9 0.94(3) . ?
C10 C11 1.379(3) . ?
C10 H10 0.92(3) . ?
C11 H11 0.93(3) . ?
C12 C13 1.476(3) . ?
C13 C17 1.382(3) . ?
C13 C14 1.391(3) . ?
C14 C15 1.361(3) . ?
C14 H14 0.91(3) . ?
C15 H15 0.90(3) . ?
C16 C17 1.368(3) . ?
C16 H16 0.92(2) . ?
C17 H17 0.87(2) . ?
C18 C19 1.381(3) . ?
C18 C23 1.387(3) . ?
C19 C20 1.385(3) . ?
C19 H19 0.90(3) . ?
C20 C21 1.378(4) . ?
C20 H20 0.95(3) . ?
C21 C22 1.373(4) . ?
C21 H21 0.95(3) . ?
C22 C23 1.384(3) . ?
C22 H22 0.96(3) . ?
C23 H23 0.94(2) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 V1 O2 108.07(8) . . ?
O1 V1 O3 104.92(8) . . ?
O2 V1 O3 94.54(7) . . ?
O1 V1 O4 103.88(8) . . ?
O2 V1 O4 92.42(6) . . ?
O3 V1 O4 146.53(6) . . ?
O1 V1 N1 103.69(7) . . ?
O2 V1 N1 147.59(7) . . ?
O3 V1 N1 83.28(6) . . ?
O4 V1 N1 73.63(6) . . ?
C5 N1 N2 115.12(15) . . ?
C5 N1 V1 129.58(13) . . ?
N2 N1 V1 114.96(11) . . ?
O3 C1 N3 123.51(17) . . ?
O3 C1 C2 129.89(17) . . ?
N3 C1 C2 106.60(16) . . ?
O7 S1 C1S 105.77(12) . . ?
O7 S1 C2S 104.65(12) . . ?
C1S S1 C2S 99.32(18) . . ?
S1 C1S H1S1 109.5 . . ?
S1 C1S H1S2 109.5 . . ?
H1S1 C1S H1S2 109.5 . . ?
S1 C1S H1S3 109.5 . . ?
H1S1 C1S H1S3 109.5 . . ?
H1S2 C1S H1S3 109.5 . . ?
C12 N2 N1 108.24(15) . . ?
C1 C2 C5 122.85(17) . . ?
C1 C2 C3 104.78(17) . . ?
C5 C2 C3 132.37(18) . . ?
S1 C2S H2S1 109.5 . . ?
S1 C2S H2S2 109.5 . . ?
H2S1 C2S H2S2 109.5 . . ?
S1 C2S H2S3 109.5 . . ?
H2S1 C2S H2S3 109.5 . . ?
H2S2 C2S H2S3 109.5 . . ?
C1 O3 V1 124.36(12) . . ?
C1 N3 N4 111.25(16) . . ?
C1 N3 C18 129.44(17) . . ?
N4 N3 C18 119.31(16) . . ?
N4 C3 C2 111.30(17) . . ?
N4 C3 C4 118.97(18) . . ?
C2 C3 C4 129.65(19) . . ?
C12 O4 V1 117.63(12) . . ?
C3 N4 N3 106.03(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 . . ?
C16 N5 C15 121.86(18) . . ?
C16 N5 H5N 116.9(17) . . ?
C15 N5 H5N 121.2(17) . . ?
N1 C5 C2 118.28(16) . . ?
N1 C5 C6 121.47(17) . . ?
C2 C5 C6 120.25(16) . . ?
C7 C6 C11 119.50(19) . . ?
C7 C6 C5 119.55(18) . . ?
C11 C6 C5 120.92(19) . . ?
C6 C7 C8 120.1(2) . . ?
C6 C7 H7 117.5(15) . . ?
C8 C7 H7 122.3(15) . . ?
C9 C8 C7 119.9(3) . . ?
C9 C8 H8 124(2) . . ?
C7 C8 H8 116(2) . . ?
C10 C9 C8 120.1(2) . . ?
C10 C9 H9 116.2(17) . . ?
C8 C9 H9 123.7(17) . . ?
C9 C10 C11 120.8(2) . . ?
C9 C10 H10 119.1(18) . . ?
C11 C10 H10 120.1(18) . . ?
C10 C11 C6 119.6(2) . . ?
C10 C11 H11 120.9(16) . . ?
C6 C11 H11 119.4(16) . . ?
N2 C12 O4 124.97(17) . . ?
N2 C12 C13 116.97(16) . . ?
O4 C12 C13 118.06(16) . . ?
C17 C13 C14 118.58(18) . . ?
C17 C13 C12 120.42(17) . . ?
C14 C13 C12 120.99(17) . . ?
C15 C14 C13 119.7(2) . . ?
C15 C14 H14 122.9(16) . . ?
C13 C14 H14 117.4(16) . . ?
N5 C15 C14 120.0(2) . . ?
N5 C15 H15 116.1(16) . . ?
C14 C15 H15 123.9(16) . . ?
N5 C16 C17 120.24(19) . . ?
N5 C16 H16 116.7(15) . . ?
C17 C16 H16 123.0(15) . . ?
C16 C17 C13 119.66(19) . . ?
C16 C17 H17 119.3(16) . . ?
C13 C17 H17 121.0(16) . . ?
C19 C18 C23 120.8(2) . . ?
C19 C18 N3 120.54(19) . . ?
C23 C18 N3 118.6(2) . . ?
C18 C19 C20 119.4(2) . . ?
C18 C19 H19 120.5(16) . . ?
C20 C19 H19 120.0(16) . . ?
C21 C20 C19 120.0(3) . . ?
C21 C20 H20 121.3(17) . . ?
C19 C20 H20 118.6(17) . . ?
C22 C21 C20 120.2(2) . . ?
C22 C21 H21 118.2(18) . . ?
C20 C21 H21 121.6(18) . . ?
C21 C22 C23 120.8(2) . . ?
C21 C22 H22 124.5(19) . . ?
C23 C22 H22 114.5(19) . . ?
C22 C23 C18 118.8(2) . . ?
C22 C23 H23 123.0(15) . . ?
C18 C23 H23 118.2(15) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 V1 N1 C5 -77.23(18) . . . . ?
O2 V1 N1 C5 114.44(19) . . . . ?
O3 V1 N1 C5 26.55(17) . . . . ?
O4 V1 N1 C5 -177.93(18) . . . . ?
O1 V1 N1 N2 95.70(14) . . . . ?
O2 V1 N1 N2 -72.63(18) . . . . ?
O3 V1 N1 N2 -160.51(13) . . . . ?
O4 V1 N1 N2 -5.00(12) . . . . ?
C5 N1 N2 C12 176.52(17) . . . . ?
V1 N1 N2 C12 2.53(19) . . . . ?
O3 C1 C2 C5 0.9(3) . . . . ?
N3 C1 C2 C5 -179.06(18) . . . . ?
O3 C1 C2 C3 -178.5(2) . . . . ?
N3 C1 C2 C3 1.5(2) . . . . ?
N3 C1 O3 V1 -147.89(16) . . . . ?
C2 C1 O3 V1 32.2(3) . . . . ?
O1 V1 O3 C1 66.90(17) . . . . ?
O2 V1 O3 C1 176.97(16) . . . . ?
O4 V1 O3 C1 -81.67(19) . . . . ?
N1 V1 O3 C1 -35.53(16) . . . . ?
O3 C1 N3 N4 177.96(18) . . . . ?
C2 C1 N3 N4 -2.1(2) . . . . ?
O3 C1 N3 C18 -2.0(3) . . . . ?
C2 C1 N3 C18 177.94(19) . . . . ?
C1 C2 C3 N4 -0.5(2) . . . . ?
C5 C2 C3 N4 -179.8(2) . . . . ?
C1 C2 C3 C4 176.1(2) . . . . ?
C5 C2 C3 C4 -3.2(4) . . . . ?
O1 V1 O4 C12 -93.83(15) . . . . ?
O2 V1 O4 C12 156.89(15) . . . . ?
O3 V1 O4 C12 54.91(19) . . . . ?
N1 V1 O4 C12 6.63(14) . . . . ?
C2 C3 N4 N3 -0.8(2) . . . . ?
C4 C3 N4 N3 -177.79(18) . . . . ?
C1 N3 N4 C3 1.8(2) . . . . ?
C18 N3 N4 C3 -178.23(18) . . . . ?
N2 N1 C5 C2 179.11(17) . . . . ?
V1 N1 C5 C2 -8.0(3) . . . . ?
N2 N1 C5 C6 0.1(3) . . . . ?
V1 N1 C5 C6 173.04(14) . . . . ?
C1 C2 C5 N1 -12.2(3) . . . . ?
C3 C2 C5 N1 167.0(2) . . . . ?
C1 C2 C5 C6 166.83(19) . . . . ?
C3 C2 C5 C6 -14.0(3) . . . . ?
N1 C5 C6 C7 113.6(2) . . . . ?
C2 C5 C6 C7 -65.4(3) . . . . ?
N1 C5 C6 C11 -68.1(3) . . . . ?
C2 C5 C6 C11 112.9(2) . . . . ?
C11 C6 C7 C8 0.2(4) . . . . ?
C5 C6 C7 C8 178.6(2) . . . . ?
C6 C7 C8 C9 -0.6(4) . . . . ?
C7 C8 C9 C10 0.2(4) . . . . ?
C8 C9 C10 C11 0.5(4) . . . . ?
C9 C10 C11 C6 -0.9(4) . . . . ?
C7 C6 C11 C10 0.5(3) . . . . ?
C5 C6 C11 C10 -177.8(2) . . . . ?
N1 N2 C12 O4 3.5(3) . . . . ?
N1 N2 C12 C13 -175.89(16) . . . . ?
V1 O4 C12 N2 -8.5(3) . . . . ?
V1 O4 C12 C13 170.87(13) . . . . ?
N2 C12 C13 C17 167.56(19) . . . . ?
O4 C12 C13 C17 -11.8(3) . . . . ?
N2 C12 C13 C14 -11.6(3) . . . . ?
O4 C12 C13 C14 169.04(19) . . . . ?
C17 C13 C14 C15 -0.1(3) . . . . ?
C12 C13 C14 C15 179.0(2) . . . . ?
C16 N5 C15 C14 -0.3(4) . . . . ?
C13 C14 C15 N5 0.5(4) . . . . ?
C15 N5 C16 C17 -0.3(3) . . . . ?
N5 C16 C17 C13 0.7(3) . . . . ?
C14 C13 C17 C16 -0.5(3) . . . . ?
C12 C13 C17 C16 -179.64(18) . . . . ?
C1 N3 C18 C19 -28.3(3) . . . . ?
N4 N3 C18 C19 151.79(19) . . . . ?
C1 N3 C18 C23 153.3(2) . . . . ?
N4 N3 C18 C23 -26.6(3) . . . . ?
C23 C18 C19 C20 -0.6(3) . . . . ?
N3 C18 C19 C20 -179.0(2) . . . . ?
C18 C19 C20 C21 -0.2(4) . . . . ?
C19 C20 C21 C22 0.8(4) . . . . ?
C20 C21 C22 C23 -0.6(4) . . . . ?
C21 C22 C23 C18 -0.2(4) . . . . ?
C19 C18 C23 C22 0.8(3) . . . . ?
N3 C18 C23 C22 179.2(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
N5 H5N O7 0.82(3) 1.84(3) 2.661(2) 178(3) 1_655
N5 H5N S1 0.82(3) 2.94(3) 3.6899(18) 153(2) 1_655

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        26.42
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.676
_refine_diff_density_min         -0.382
_refine_diff_density_rms         0.108
####################################################################### 
# 
# 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_compound12
_database_code_depnum_ccdc_archive 'CCDC 1502029'
_audit_update_record             
;
2016-09-01 deposited with the CCDC.
2016-09-15 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C22 H17 N4 O5 V'
_chemical_formula_sum            'C23 H19 N4 O5 V'
_chemical_formula_weight         482.36

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   C2/c
_symmetry_space_group_name_Hall  -C2yc

loop_
_symmetry_equiv_pos_as_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                   14.133(4)
_cell_length_b                   11.772(4)
_cell_length_c                   26.621(8)
_cell_angle_alpha                90.00
_cell_angle_beta                 103.350(17)
_cell_angle_gamma                90.00
_cell_volume                     4309(2)
_cell_formula_units_Z            8
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    28937
_cell_measurement_theta_min      4.555
_cell_measurement_theta_max      46.750

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.487
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1984
_exptl_absorpt_coefficient_mu    0.504
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8634
_exptl_absorpt_correction_T_max  0.9513
_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  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            28005
_diffrn_reflns_av_R_equivalents  0.0431
_diffrn_reflns_av_unetI/netI     0.0486
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -35
_diffrn_reflns_limit_l_max       35
_diffrn_reflns_theta_min         1.57
_diffrn_reflns_theta_max         28.43
_reflns_number_total             5328
_reflns_number_gt                3431
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Apex2, Bruker Instrument Service v2010, 1-2'
_computing_cell_refinement       
'SAINT V7.68A (Bruker: Madison, 2009 ) in Apex2 suite'
_computing_data_reduction        
'SAINT and XPREP Version 2008/2 (Sheldrick, Bruker AXS Inc.)'
_computing_structure_solution    
'XS V2008/1 (G. M. Sheldrick, Acta Cryst. (2008). A64, 112-122)'
_computing_structure_refinement  
'XL V2008/4 (G. M. Sheldrick, Acta Cryst. (2008). A64, 112-122)'
_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)+(0.0687P)²+3.4050P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         5328
_refine_ls_number_parameters     348
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0921
_refine_ls_R_factor_gt           0.0495
_refine_ls_wR_factor_ref         0.1476
_refine_ls_wR_factor_gt          0.1237
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_restrained_S_all      1.060
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
V1 V 0.24892(3) 0.08110(4) 0.595888(19) 0.03835(16) Uani 1 1 d . . .
O1 O 0.20339(16) 0.08174(18) 0.64452(9) 0.0586(6) Uani 1 1 d . . .
N1 N 0.27501(14) 0.25602(18) 0.58989(8) 0.0351(5) Uani 1 1 d . . .
C1 C 0.44158(18) 0.1461(2) 0.64712(10) 0.0368(6) Uani 1 1 d . . .
C1S C 0.2805(3) -0.0869(3) 0.52911(14) 0.0699(10) Uani 1 1 d . . .
H1S1 H 0.2746 -0.0226 0.5065 0.105 Uiso 1 1 calc R . .
H1S2 H 0.2451 -0.1499 0.5109 0.105 Uiso 1 1 calc R . .
H1S3 H 0.3478 -0.1072 0.5407 0.105 Uiso 1 1 calc R . .
N2 N 0.19906(15) 0.31618(18) 0.55680(9) 0.0390(5) Uani 1 1 d . . .
C2 C 0.42952(18) 0.2637(2) 0.64688(10) 0.0365(6) Uani 1 1 d . . .
O2 O 0.24191(15) -0.05918(16) 0.57233(9) 0.0513(5) Uani 1 1 d . . .
O3 O 0.38357(13) 0.06862(15) 0.62135(8) 0.0431(5) Uani 1 1 d . . .
C3 C 0.51639(19) 0.3046(2) 0.68116(11) 0.0414(7) Uani 1 1 d . . .
N3 N 0.52661(15) 0.1206(2) 0.67950(9) 0.0401(5) Uani 1 1 d . . .
O4 O 0.15102(13) 0.13093(15) 0.53955(8) 0.0454(5) Uani 1 1 d . . .
N4 N 0.57365(16) 0.2197(2) 0.70069(9) 0.0457(6) Uani 1 1 d . . .
C4 C 0.5485(2) 0.4232(3) 0.69547(15) 0.0617(9) Uani 1 1 d . . .
H4A H 0.6007 0.4222 0.7258 0.093 Uiso 1 1 calc R . .
H4B H 0.4950 0.4660 0.7023 0.093 Uiso 1 1 calc R . .
H4C H 0.5705 0.4578 0.6676 0.093 Uiso 1 1 calc R . .
O5 O 0.03008(15) 0.38432(18) 0.48319(8) 0.0557(6) Uani 1 1 d . . .
C5 C 0.34701(18) 0.3190(2) 0.61610(10) 0.0337(6) Uani 1 1 d . . .
C6 C 0.34268(18) 0.4461(2) 0.61644(10) 0.0339(6) Uani 1 1 d . . .
C7 C 0.3953(3) 0.5123(3) 0.59009(13) 0.0531(8) Uani 1 1 d . . .
H7 H 0.429(2) 0.478(3) 0.5696(12) 0.060(10) Uiso 1 1 d . . .
C8 C 0.3976(3) 0.6287(3) 0.59620(14) 0.0608(9) Uani 1 1 d . . .
H8 H 0.429(3) 0.675(3) 0.5798(14) 0.085(13) Uiso 1 1 d . . .
C9 C 0.3492(2) 0.6798(3) 0.62848(14) 0.0534(8) Uani 1 1 d . . .
H9 H 0.352(2) 0.755(3) 0.6336(11) 0.051(9) Uiso 1 1 d . . .
C10 C 0.2942(2) 0.6155(3) 0.65376(13) 0.0503(8) Uani 1 1 d . . .
H10 H 0.261(3) 0.646(3) 0.6769(14) 0.075(11) Uiso 1 1 d . . .
C11 C 0.2911(2) 0.4985(3) 0.64795(12) 0.0434(7) Uani 1 1 d . . .
H11 H 0.256(3) 0.455(3) 0.6645(13) 0.069(11) Uiso 1 1 d . . .
C12 C 0.56959(19) 0.0126(2) 0.69529(11) 0.0402(6) Uani 1 1 d . . .
C13 C 0.6334(2) 0.0039(3) 0.74261(12) 0.0503(8) Uani 1 1 d . . .
H13 H 0.651(2) 0.072(3) 0.7641(13) 0.065(10) Uiso 1 1 d . . .
C14 C 0.6765(3) -0.0994(3) 0.75826(14) 0.0607(9) Uani 1 1 d . . .
H14 H 0.721(3) -0.102(3) 0.7914(13) 0.065(10) Uiso 1 1 d . . .
C15 C 0.6554(3) -0.1934(3) 0.72671(15) 0.0637(10) Uani 1 1 d . . .
H15 H 0.680(3) -0.258(3) 0.7372(13) 0.069(11) Uiso 1 1 d . . .
C16 C 0.5910(2) -0.1851(3) 0.67946(15) 0.0592(9) Uani 1 1 d . . .
H16 H 0.573(3) -0.250(3) 0.6571(14) 0.081(12) Uiso 1 1 d . . .
C17 C 0.5473(2) -0.0818(3) 0.66351(14) 0.0508(8) Uani 1 1 d . . .
H17 H 0.511(2) -0.076(2) 0.6338(12) 0.046(9) Uiso 1 1 d . . .
C18 C 0.13763(18) 0.2419(2) 0.53267(10) 0.0369(6) Uani 1 1 d . . .
C19 C 0.04887(19) 0.2733(2) 0.49642(10) 0.0385(6) Uani 1 1 d . . .
C20 C -0.0245(2) 0.2070(2) 0.47117(11) 0.0432(7) Uani 1 1 d . . .
H20 H -0.0289 0.1285 0.4735 0.052 Uiso 1 1 calc R . .
C21 C -0.0929(2) 0.2800(3) 0.44059(12) 0.0522(8) Uani 1 1 d . . .
H21 H -0.152(3) 0.268(3) 0.4192(13) 0.076(11) Uiso 1 1 d . . .
C22 C -0.0581(2) 0.3842(3) 0.44865(13) 0.0573(9) Uani 1 1 d . . .
H22 H -0.080(2) 0.455(3) 0.4370(13) 0.067(10) Uiso 1 1 d . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
V1 O1 1.573(2) . ?
V1 O2 1.761(2) . ?
V1 O3 1.8727(19) . ?
V1 O4 1.8840(19) . ?
V1 N1 2.104(2) . ?
N1 C5 1.321(3) . ?
N1 N2 1.412(3) . ?
C1 O3 1.310(3) . ?
C1 N3 1.341(3) . ?
C1 C2 1.394(4) . ?
C1S O2 1.420(4) . ?
C1S H1S1 0.9600 . ?
C1S H1S2 0.9600 . ?
C1S H1S3 0.9600 . ?
N2 C18 1.294(3) . ?
C2 C5 1.419(3) . ?
C2 C3 1.433(4) . ?
C3 N4 1.315(4) . ?
C3 C4 1.490(4) . ?
N3 N4 1.395(3) . ?
N3 C12 1.430(4) . ?
O4 C18 1.327(3) . ?
C4 H4A 0.9600 . ?
C4 H4B 0.9600 . ?
C4 H4C 0.9600 . ?
O5 C19 1.363(3) . ?
O5 C22 1.367(4) . ?
C5 C6 1.497(4) . ?
C6 C7 1.375(4) . ?
C6 C11 1.378(4) . ?
C7 C8 1.379(5) . ?
C7 H7 0.90(3) . ?
C8 C9 1.356(5) . ?
C8 H8 0.88(4) . ?
C9 C10 1.369(5) . ?
C9 H9 0.89(3) . ?
C10 C11 1.385(4) . ?
C10 H10 0.93(4) . ?
C11 H11 0.89(4) . ?
C12 C13 1.373(4) . ?
C12 C17 1.389(4) . ?
C13 C14 1.380(5) . ?
C13 H13 0.98(3) . ?
C14 C15 1.380(5) . ?
C14 H14 0.95(3) . ?
C15 C16 1.375(5) . ?
C15 H15 0.86(4) . ?
C16 C17 1.385(4) . ?
C16 H16 0.97(4) . ?
C17 H17 0.84(3) . ?
C18 C19 1.443(3) . ?
C19 C20 1.347(4) . ?
C20 C21 1.405(4) . ?
C20 H20 0.9300 . ?
C21 C22 1.321(5) . ?
C21 H21 0.90(4) . ?
C22 H22 0.92(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
O1 V1 O2 107.31(12) . . ?
O1 V1 O3 106.09(11) . . ?
O2 V1 O3 91.39(9) . . ?
O1 V1 O4 106.79(11) . . ?
O2 V1 O4 92.17(9) . . ?
O3 V1 O4 144.17(9) . . ?
O1 V1 N1 99.78(10) . . ?
O2 V1 N1 152.49(10) . . ?
O3 V1 N1 85.58(8) . . ?
O4 V1 N1 75.19(8) . . ?
C5 N1 N2 115.5(2) . . ?
C5 N1 V1 129.54(17) . . ?
N2 N1 V1 114.63(15) . . ?
O3 C1 N3 122.7(2) . . ?
O3 C1 C2 128.9(2) . . ?
N3 C1 C2 108.4(2) . . ?
O2 C1S H1S1 109.5 . . ?
O2 C1S H1S2 109.5 . . ?
H1S1 C1S H1S2 109.5 . . ?
O2 C1S H1S3 109.5 . . ?
H1S1 C1S H1S3 109.5 . . ?
H1S2 C1S H1S3 109.5 . . ?
C18 N2 N1 107.3(2) . . ?
C1 C2 C5 122.8(2) . . ?
C1 C2 C3 104.2(2) . . ?
C5 C2 C3 133.0(3) . . ?
C1S O2 V1 120.25(19) . . ?
C1 O3 V1 126.56(17) . . ?
N4 C3 C2 110.8(2) . . ?
N4 C3 C4 119.2(2) . . ?
C2 C3 C4 130.0(3) . . ?
C1 N3 N4 110.2(2) . . ?
C1 N3 C12 130.2(2) . . ?
N4 N3 C12 119.6(2) . . ?
C18 O4 V1 118.14(16) . . ?
C3 N4 N3 106.4(2) . . ?
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 . . ?
C19 O5 C22 105.4(2) . . ?
N1 C5 C2 118.5(2) . . ?
N1 C5 C6 122.5(2) . . ?
C2 C5 C6 119.0(2) . . ?
C7 C6 C11 118.8(3) . . ?
C7 C6 C5 122.3(2) . . ?
C11 C6 C5 118.6(2) . . ?
C6 C7 C8 120.2(3) . . ?
C6 C7 H7 119(2) . . ?
C8 C7 H7 121(2) . . ?
C9 C8 C7 120.9(3) . . ?
C9 C8 H8 116(3) . . ?
C7 C8 H8 124(3) . . ?
C8 C9 C10 119.5(3) . . ?
C8 C9 H9 122(2) . . ?
C10 C9 H9 119(2) . . ?
C9 C10 C11 120.2(3) . . ?
C9 C10 H10 123(2) . . ?
C11 C10 H10 117(2) . . ?
C6 C11 C10 120.3(3) . . ?
C6 C11 H11 118(2) . . ?
C10 C11 H11 121(2) . . ?
C13 C12 C17 120.5(3) . . ?
C13 C12 N3 118.8(3) . . ?
C17 C12 N3 120.8(3) . . ?
C12 C13 C14 119.6(3) . . ?
C12 C13 H13 120(2) . . ?
C14 C13 H13 120(2) . . ?
C15 C14 C13 120.3(3) . . ?
C15 C14 H14 123(2) . . ?
C13 C14 H14 117(2) . . ?
C16 C15 C14 120.2(3) . . ?
C16 C15 H15 120(2) . . ?
C14 C15 H15 120(2) . . ?
C15 C16 C17 119.8(4) . . ?
C15 C16 H16 122(2) . . ?
C17 C16 H16 118(2) . . ?
C16 C17 C12 119.6(3) . . ?
C16 C17 H17 119(2) . . ?
C12 C17 H17 121(2) . . ?
N2 C18 O4 122.6(2) . . ?
N2 C18 C19 122.6(2) . . ?
O4 C18 C19 114.8(2) . . ?
C20 C19 O5 110.2(2) . . ?
C20 C19 C18 129.4(3) . . ?
O5 C19 C18 120.4(2) . . ?
C19 C20 C21 106.4(3) . . ?
C19 C20 H20 126.8 . . ?
C21 C20 H20 126.8 . . ?
C22 C21 C20 107.0(3) . . ?
C22 C21 H21 120(2) . . ?
C20 C21 H21 133(2) . . ?
C21 C22 O5 111.0(3) . . ?
C21 C22 H22 135(2) . . ?
O5 C22 H22 114(2) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 V1 N1 C5 79.9(2) . . . . ?
O2 V1 N1 C5 -110.2(3) . . . . ?
O3 V1 N1 C5 -25.7(2) . . . . ?
O4 V1 N1 C5 -175.2(2) . . . . ?
O1 V1 N1 N2 -92.80(19) . . . . ?
O2 V1 N1 N2 77.1(3) . . . . ?
O3 V1 N1 N2 161.61(18) . . . . ?
O4 V1 N1 N2 12.13(17) . . . . ?
C5 N1 N2 C18 177.1(2) . . . . ?
V1 N1 N2 C18 -9.1(3) . . . . ?
O3 C1 C2 C5 -0.5(4) . . . . ?
N3 C1 C2 C5 179.4(2) . . . . ?
O3 C1 C2 C3 -178.6(3) . . . . ?
N3 C1 C2 C3 1.3(3) . . . . ?
O1 V1 O2 C1S -178.1(2) . . . . ?
O3 V1 O2 C1S -70.7(2) . . . . ?
O4 V1 O2 C1S 73.6(2) . . . . ?
N1 V1 O2 C1S 12.4(3) . . . . ?
N3 C1 O3 V1 155.1(2) . . . . ?
C2 C1 O3 V1 -24.9(4) . . . . ?
O1 V1 O3 C1 -69.2(2) . . . . ?
O2 V1 O3 C1 -177.7(2) . . . . ?
O4 V1 O3 C1 86.7(3) . . . . ?
N1 V1 O3 C1 29.7(2) . . . . ?
C1 C2 C3 N4 -1.2(3) . . . . ?
C5 C2 C3 N4 -179.0(3) . . . . ?
C1 C2 C3 C4 177.4(3) . . . . ?
C5 C2 C3 C4 -0.4(5) . . . . ?
O3 C1 N3 N4 178.9(2) . . . . ?
C2 C1 N3 N4 -1.1(3) . . . . ?
O3 C1 N3 C12 -3.8(4) . . . . ?
C2 C1 N3 C12 176.2(3) . . . . ?
O1 V1 O4 C18 83.2(2) . . . . ?
O2 V1 O4 C18 -168.0(2) . . . . ?
O3 V1 O4 C18 -72.6(2) . . . . ?
N1 V1 O4 C18 -12.74(19) . . . . ?
C2 C3 N4 N3 0.5(3) . . . . ?
C4 C3 N4 N3 -178.2(3) . . . . ?
C1 N3 N4 C3 0.3(3) . . . . ?
C12 N3 N4 C3 -177.3(2) . . . . ?
N2 N1 C5 C2 -174.9(2) . . . . ?
V1 N1 C5 C2 12.5(4) . . . . ?
N2 N1 C5 C6 8.0(4) . . . . ?
V1 N1 C5 C6 -164.59(18) . . . . ?
C1 C2 C5 N1 5.8(4) . . . . ?
C3 C2 C5 N1 -176.8(3) . . . . ?
C1 C2 C5 C6 -177.1(2) . . . . ?
C3 C2 C5 C6 0.4(4) . . . . ?
N1 C5 C6 C7 -106.5(3) . . . . ?
C2 C5 C6 C7 76.4(3) . . . . ?
N1 C5 C6 C11 79.4(3) . . . . ?
C2 C5 C6 C11 -97.6(3) . . . . ?
C11 C6 C7 C8 1.4(5) . . . . ?
C5 C6 C7 C8 -172.6(3) . . . . ?
C6 C7 C8 C9 0.6(5) . . . . ?
C7 C8 C9 C10 -2.6(5) . . . . ?
C8 C9 C10 C11 2.5(5) . . . . ?
C7 C6 C11 C10 -1.5(4) . . . . ?
C5 C6 C11 C10 172.8(3) . . . . ?
C9 C10 C11 C6 -0.4(4) . . . . ?
C1 N3 C12 C13 -153.1(3) . . . . ?
N4 N3 C12 C13 24.0(4) . . . . ?
C1 N3 C12 C17 26.9(4) . . . . ?
N4 N3 C12 C17 -156.0(3) . . . . ?
C17 C12 C13 C14 0.8(5) . . . . ?
N3 C12 C13 C14 -179.3(3) . . . . ?
C12 C13 C14 C15 -0.2(5) . . . . ?
C13 C14 C15 C16 -0.2(6) . . . . ?
C14 C15 C16 C17 0.1(6) . . . . ?
C15 C16 C17 C12 0.5(5) . . . . ?
C13 C12 C17 C16 -0.9(5) . . . . ?
N3 C12 C17 C16 179.1(3) . . . . ?
N1 N2 C18 O4 -1.3(3) . . . . ?
N1 N2 C18 C19 178.3(2) . . . . ?
V1 O4 C18 N2 12.7(3) . . . . ?
V1 O4 C18 C19 -166.86(18) . . . . ?
C22 O5 C19 C20 0.0(3) . . . . ?
C22 O5 C19 C18 179.8(3) . . . . ?
N2 C18 C19 C20 -175.1(3) . . . . ?
O4 C18 C19 C20 4.5(4) . . . . ?
N2 C18 C19 O5 5.1(4) . . . . ?
O4 C18 C19 O5 -175.3(2) . . . . ?
O5 C19 C20 C21 -0.1(3) . . . . ?
C18 C19 C20 C21 -179.9(3) . . . . ?
C19 C20 C21 C22 0.2(4) . . . . ?
C20 C21 C22 O5 -0.2(4) . . . . ?
C19 O5 C22 C21 0.1(4) . . . . ?

_diffrn_measured_fraction_theta_max 0.980
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.272
_refine_diff_density_min         -0.380
_refine_diff_density_rms         0.070
