# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 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_2
_database_code_depnum_ccdc_archive 'CCDC 914805'
_audit_update_record             
;
2016-01-29 deposited with the CCDC.
2016-08-31 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C21 H21 Cl N5 O9 V'
_chemical_formula_weight         573.82

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
V V 0.3005 0.5294 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   P-1

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

_cell_length_a                   7.1370(4)
_cell_length_b                   12.7274(7)
_cell_length_c                   14.9056(9)
_cell_angle_alpha                68.085(4)
_cell_angle_beta                 79.864(4)
_cell_angle_gamma                88.108(4)
_cell_volume                     1235.72(12)
_cell_formula_units_Z            2
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    17396
_cell_measurement_theta_min      1.50
_cell_measurement_theta_max      25.00

_exptl_crystal_description       needle
_exptl_crystal_colour            red
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.06
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.542
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             588
_exptl_absorpt_coefficient_mu    0.570
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.947
_exptl_absorpt_correction_T_max  0.966
_exptl_absorpt_process_details   Sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      298(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_reflns_number            17550
_diffrn_reflns_av_R_equivalents  0.0471
_diffrn_reflns_av_sigmaI/netI    0.0498
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         1.50
_diffrn_reflns_theta_max         25.00
_reflns_number_total             4333
_reflns_number_gt                3242
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'SMART APEX II (Bruker,2010)'
_computing_cell_refinement       'SMART APEX II'
_computing_data_reduction        'SAINT (Bruker,2000)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  Mercury

_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)+(0.0793P)²+1.0820P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4333
_refine_ls_number_parameters     367
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0753
_refine_ls_R_factor_gt           0.0536
_refine_ls_wR_factor_ref         0.1556
_refine_ls_wR_factor_gt          0.1419
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_restrained_S_all      1.033
_refine_ls_shift/su_max          0.039
_refine_ls_shift/su_mean         0.003

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 0.06155(8) 1.00584(5) 0.19517(4) 0.0313(2) Uani 1 1 d . A 4
O2 O -0.1527(4) 1.0862(2) 0.2155(2) 0.0467(7) Uani 1 1 d . A 4
O4 O 0.1864(4) 1.0754(2) 0.29196(19) 0.0420(7) Uani 1 1 d . A 4
H4B H 0.3173 1.0726 0.2904 0.050 Uiso 1 1 calc R A 4
O1 O 0.0012(4) 0.9436(2) 0.12837(19) 0.0418(7) Uani 1 1 d . A 4
N2 N -0.0742(4) 0.8842(2) 0.3321(2) 0.0316(7) Uani 1 1 d . A 4
N1 N 0.2700(4) 0.8826(2) 0.2461(2) 0.0306(7) Uani 1 1 d . A 4
N3 N 0.3264(4) 1.0722(2) 0.1015(2) 0.0333(7) Uani 1 1 d . A 4
O3 O -0.0159(4) 1.1526(2) 0.1338(2) 0.0510(8) Uani 1 1 d . A 4
N5 N 0.6381(4) 1.0601(3) 0.0593(2) 0.0370(8) Uani 1 1 d . A 4
H5A H 0.7494 1.0321 0.0585 0.044 Uiso 1 1 calc R A 4
N4 N -0.0755(4) 0.7166(3) 0.4531(2) 0.0392(8) Uani 1 1 d . A 4
H4A H -0.0365 0.6525 0.4888 0.047 Uiso 1 1 calc R A 4
Cl1 Cl 0.06562(16) 0.49990(9) 0.67390(8) 0.0525(3) Uani 1 1 d . B 4
C12 C 0.3948(5) 1.1731(3) 0.0255(3) 0.0350(9) Uani 1 1 d . A 4
C1 C 0.2185(5) 0.7868(3) 0.3245(3) 0.0331(8) Uani 1 1 d . A 4
C5 C 0.4499(5) 0.8971(3) 0.1972(3) 0.0328(8) Uani 1 1 d . A 4
C6 C 0.4761(5) 1.0087(3) 0.1188(3) 0.0315(8) Uani 1 1 d . A 4
C15 C -0.2491(5) 0.8663(3) 0.3951(3) 0.0329(8) Uani 1 1 d . A 4
C13 C 0.0231(5) 0.7918(3) 0.3707(3) 0.0327(8) Uani 1 1 d . A 4
C14 C -0.2511(5) 0.7605(3) 0.4707(3) 0.0365(9) Uani 1 1 d . A 4
C20 C 0.0734(8) 1.1236(5) 0.3556(4) 0.0751(16) Uani 1 1 d . A 4
H19A H 0.0383 1.1983 0.3173 0.113 Uiso 1 1 calc R A 4
H19B H 0.1458 1.1279 0.4027 0.113 Uiso 1 1 calc R A 4
H19C H -0.0394 1.0768 0.3893 0.113 Uiso 1 1 calc R A 4
O5 O 0.1359(15) 0.5177(4) 0.5774(4) 0.184(4) Uani 1 1 d . B 4
O6 O 0.0424(5) 0.3833(3) 0.7341(3) 0.0735(10) Uani 1 1 d . B 4
C16 C -0.4095(6) 0.9324(3) 0.3928(3) 0.0399(9) Uani 1 1 d . A 4
H17 H -0.4121 1.0034 0.3434 0.048 Uiso 1 1 calc R A 4
C11 C 0.3027(6) 1.2704(3) -0.0228(3) 0.0464(10) Uani 1 1 d . A 4
H11 H 0.1718 1.2759 -0.0069 0.056 Uiso 1 1 calc R A 4
C2 C 0.3417(6) 0.7006(3) 0.3544(3) 0.0416(10) Uani 1 1 d . A 4
H2 H 0.3025 0.6344 0.4083 0.050 Uiso 1 1 calc R A 4
C8 C 0.7036(6) 1.2556(4) -0.0729(3) 0.0482(11) Uani 1 1 d . A 4
H8 H 0.8345 1.2505 -0.0894 0.058 Uiso 1 1 calc R A 4
C18 C -0.5633(6) 0.7815(4) 0.5410(3) 0.0498(11) Uani 1 1 d . A 4
H15 H -0.6715 0.7548 0.5890 0.060 Uiso 1 1 calc R A 4
C9 C 0.6103(7) 1.3515(4) -0.1188(3) 0.0542(12) Uani 1 1 d . A 4
H9 H 0.6801 1.4136 -0.1669 0.065 Uiso 1 1 calc R A 4
C4 C 0.5826(5) 0.8146(3) 0.2230(3) 0.0380(9) Uani 1 1 d . A 4
H4 H 0.7066 0.8258 0.1883 0.046 Uiso 1 1 calc R A 4
C19 C -0.4076(6) 0.7151(4) 0.5451(3) 0.0462(10) Uani 1 1 d . A 4
H14 H -0.4064 0.6441 0.5946 0.055 Uiso 1 1 calc R A 4
C7 C 0.5916(5) 1.1666(3) -0.0004(3) 0.0375(9) Uani 1 1 d . A 4
C17 C -0.5639(6) 0.8879(4) 0.4668(3) 0.0473(11) Uani 1 1 d . A 4
H16 H -0.6723 0.9303 0.4671 0.057 Uiso 1 1 calc R A 4
C3 C 0.5258(6) 0.7148(3) 0.3020(3) 0.0440(10) Uani 1 1 d . A 4
H3 H 0.6114 0.6572 0.3200 0.053 Uiso 1 1 calc R A 4
C10 C 0.4128(7) 1.3581(4) -0.0951(3) 0.0549(12) Uani 1 1 d . A 4
H10 H 0.3544 1.4237 -0.1293 0.066 Uiso 1 1 calc R A 4
O8A O -0.081(2) 0.5675(8) 0.6891(9) 0.112(7) Uani 0.60(3) 1 d P C 1
O7A O 0.135(5) 0.5589(12) 0.7193(11) 0.171(12) Uani 0.60(3) 1 d P D 1
O9 O 0.5011(6) 0.2100(3) 0.2170(3) 0.0854(12) Uani 1 1 d . . .
H9A H 0.6017 0.1883 0.1949 0.128 Uiso 1 1 calc R . .
C21 C 0.5010(13) 0.3241(5) 0.1779(5) 0.119(3) Uani 1 1 d . . .
H21A H 0.3722 0.3483 0.1779 0.179 Uiso 1 1 calc R . .
H21B H 0.5699 0.3507 0.1117 0.179 Uiso 1 1 calc R . .
H21C H 0.5608 0.3546 0.2162 0.179 Uiso 1 1 calc R . .
O8B O -0.103(3) 0.522(2) 0.638(2) 0.149(18) Uani 0.40(3) 1 d P C 2
O7B O 0.2446(18) 0.5311(12) 0.679(2) 0.123(12) Uani 0.40(3) 1 d P D 2


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
V1 O1 1.602(3) . ?
V1 O2 1.855(3) . ?
V1 O3 1.862(3) . ?
V1 N3 2.129(3) . ?
V1 N2 2.132(3) . ?
V1 N1 2.146(3) . ?
V1 O4 2.262(3) . ?
O2 O3 1.420(4) . ?
O4 C20 1.434(5) . ?
O4 H4B 0.9300 . ?
N2 C13 1.333(5) . ?
N2 C15 1.392(4) . ?
N1 C5 1.341(4) . ?
N1 C1 1.342(4) . ?
N3 C6 1.321(5) . ?
N3 C12 1.389(4) . ?
N5 C6 1.344(4) . ?
N5 C7 1.383(5) . ?
N5 H5A 0.8600 . ?
N4 C13 1.335(5) . ?
N4 C14 1.378(5) . ?
N4 H4A 0.8600 . ?
Cl1 O5 1.373(5) . ?
Cl1 O6 1.416(3) . ?
Cl1 O7A 1.338(9) . ?
Cl1 O8A 1.374(11) . ?
Cl1 O7B 1.373(9) . ?
Cl1 O8B 1.380(11) . ?
C12 C11 1.390(6) . ?
C12 C7 1.398(5) . ?
C1 C2 1.372(5) . ?
C1 C13 1.454(5) . ?
C5 C4 1.382(5) . ?
C5 C6 1.456(5) . ?
C15 C14 1.395(5) . ?
C15 C16 1.396(5) . ?
C14 C19 1.393(5) . ?
C20 H19A 0.9600 . ?
C20 H19B 0.9600 . ?
C20 H19C 0.9600 . ?
C16 C17 1.378(5) . ?
C16 H17 0.9300 . ?
C11 C10 1.373(6) . ?
C11 H11 0.9300 . ?
C2 C3 1.385(6) . ?
C2 H2 0.9300 . ?
C8 C9 1.373(6) . ?
C8 C7 1.390(5) . ?
C8 H8 0.9300 . ?
C18 C19 1.370(6) . ?
C18 C17 1.393(6) . ?
C18 H15 0.9300 . ?
C9 C10 1.399(6) . ?
C9 H9 0.9300 . ?
C4 C3 1.383(6) . ?
C4 H4 0.9300 . ?
C19 H14 0.9300 . ?
C17 H16 0.9300 . ?
C3 H3 0.9300 . ?
C10 H10 0.9300 . ?
O9 C21 1.348(6) . ?
O9 H9A 0.8200 . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 V1 O2 102.67(14) . . ?
O1 V1 O3 101.61(14) . . ?
O2 V1 O3 44.94(11) . . ?
O1 V1 N3 94.73(12) . . ?
O2 V1 N3 127.22(12) . . ?
O3 V1 N3 83.02(12) . . ?
O1 V1 N2 95.96(12) . . ?
O2 V1 N2 81.79(11) . . ?
O3 V1 N2 126.23(12) . . ?
N3 V1 N2 145.61(12) . . ?
O1 V1 N1 92.19(12) . . ?
O2 V1 N1 152.55(12) . . ?
O3 V1 N1 153.49(12) . . ?
N3 V1 N1 73.29(11) . . ?
N2 V1 N1 73.72(11) . . ?
O1 V1 O4 170.91(12) . . ?
O2 V1 O4 86.25(12) . . ?
O3 V1 O4 85.91(12) . . ?
N3 V1 O4 81.01(11) . . ?
N2 V1 O4 83.44(11) . . ?
N1 V1 O4 78.92(10) . . ?
O3 O2 V1 67.78(15) . . ?
C20 O4 V1 123.1(3) . . ?
C20 O4 H4B 118.4 . . ?
V1 O4 H4B 118.4 . . ?
C13 N2 C15 105.3(3) . . ?
C13 N2 V1 116.0(2) . . ?
C15 N2 V1 138.5(2) . . ?
C5 N1 C1 119.3(3) . . ?
C5 N1 V1 120.7(2) . . ?
C1 N1 V1 120.0(2) . . ?
C6 N3 C12 105.8(3) . . ?
C6 N3 V1 117.1(2) . . ?
C12 N3 V1 136.9(2) . . ?
O2 O3 V1 67.28(15) . . ?
C6 N5 C7 106.9(3) . . ?
C6 N5 H5A 126.5 . . ?
C7 N5 H5A 126.5 . . ?
C13 N4 C14 107.5(3) . . ?
C13 N4 H4A 126.2 . . ?
C14 N4 H4A 126.2 . . ?
O5 Cl1 O6 112.5(3) . . ?
O5 Cl1 O7A 121.2(10) . . ?
O5 Cl1 O7B 86.5(12) . . ?
O5 Cl1 O8A 115.4(6) . . ?
O5 Cl1 O8B 81.3(12) . . ?
O6 Cl1 O7A 111.1(7) . . ?
O6 CL1 O7B 105.1(9) . . ?
O6 Cl1 O8A 116.3(5) . . ?
O6 Cl1 O8B 102.6(11) . . ?
O7A Cl1 O8A 76.0(14) . . ?
O7A Cl1 O8B 124.3(17) . . ?
O7B Cl1 O8A 117.1(10) . . ?
O7B Cl1 O8B 152.3(15) . . ?
N3 C12 C11 131.4(4) . . ?
N3 C12 C7 108.4(3) . . ?
C11 C12 C7 120.2(4) . . ?
N1 C1 C2 122.3(3) . . ?
N1 C1 C13 110.4(3) . . ?
C2 C1 C13 127.3(3) . . ?
N1 C5 C4 121.9(3) . . ?
N1 C5 C6 109.8(3) . . ?
C4 C5 C6 128.3(3) . . ?
N3 C6 N5 112.7(3) . . ?
N3 C6 C5 118.8(3) . . ?
N5 C6 C5 128.5(3) . . ?
N2 C15 C14 108.6(3) . . ?
N2 C15 C16 131.8(3) . . ?
C14 C15 C16 119.6(3) . . ?
N2 C13 N4 112.6(3) . . ?
N2 C13 C1 118.9(3) . . ?
N4 C13 C1 128.4(3) . . ?
N4 C14 C19 130.6(4) . . ?
N4 C14 C15 106.0(3) . . ?
C19 C14 C15 123.4(4) . . ?
C17 C16 C15 117.1(4) . . ?
C17 C16 H17 121.5 . . ?
C15 C16 H17 121.5 . . ?
C10 C11 C12 117.3(4) . . ?
C10 C11 H11 121.3 . . ?
C12 C11 H11 121.3 . . ?
C1 C2 C3 118.2(4) . . ?
C1 C2 H2 120.9 . . ?
C3 C2 H2 120.9 . . ?
C9 C8 C7 116.3(4) . . ?
C9 C8 H8 121.9 . . ?
C7 C8 H8 121.9 . . ?
C19 C18 C17 121.7(4) . . ?
C19 C18 H15 119.2 . . ?
C17 C18 H15 119.2 . . ?
C8 C9 C10 121.7(4) . . ?
C8 C9 H9 119.2 . . ?
C10 C9 H9 119.2 . . ?
C5 C4 C3 118.2(4) . . ?
C5 C4 H4 120.9 . . ?
C3 C4 H4 120.9 . . ?
C18 C19 C14 115.9(4) . . ?
C18 C19 H14 122.1 . . ?
C14 C19 H14 122.1 . . ?
N5 C7 C8 131.3(4) . . ?
N5 C7 C12 106.1(3) . . ?
C8 C7 C12 122.6(4) . . ?
C16 C17 C18 122.4(4) . . ?
C16 C17 H16 118.8 . . ?
C18 C17 H16 118.8 . . ?
C4 C3 C2 120.1(4) . . ?
C4 C3 H3 119.9 . . ?
C2 C3 H3 119.9 . . ?
C11 C10 C9 121.9(4) . . ?
C11 C10 H10 119.1 . . ?
C9 C10 H10 119.1 . . ?
C21 O9 H9A 109.5 . . ?
O9 C21 H21A 109.5 . . ?
O9 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
O9 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?

_diffrn_measured_fraction_theta_max 0.994
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.994
_refine_diff_density_max         0.660
_refine_diff_density_min         -0.464
_refine_diff_density_rms         0.070
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_1
_database_code_depnum_ccdc_archive 'CCDC 1407332'
_audit_update_record             
;
2016-01-29 deposited with the CCDC.
2016-08-31 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C22 H20 N6 O3 V'
_chemical_formula_weight         467.38

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

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   P-1

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

_cell_length_a                   9.3945(2)
_cell_length_b                   9.7730(3)
_cell_length_c                   11.4652(3)
_cell_angle_alpha                95.855(2)
_cell_angle_beta                 92.247(2)
_cell_angle_gamma                98.309(2)
_cell_volume                     1034.61(5)
_cell_formula_units_Z            2
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    17396
_cell_measurement_theta_min      1.79
_cell_measurement_theta_max      27.53

_exptl_crystal_description       Needle
_exptl_crystal_colour            Yellow
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.07
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.500
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             482
_exptl_absorpt_coefficient_mu    0.518
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.946
_exptl_absorpt_correction_T_max  0.964
_exptl_absorpt_process_details   Sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      298(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_reflns_number            17396
_diffrn_reflns_av_R_equivalents  0.0333
_diffrn_reflns_av_sigmaI/netI    0.0473
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         1.79
_diffrn_reflns_theta_max         27.53
_reflns_number_total             4730
_reflns_number_gt                3505
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'SMART APEX II (Bruker,2010)'
_computing_cell_refinement       'SMART APEX II'
_computing_data_reduction        'SAINT (Bruker,2000)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  Mercury

_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)+(0.0528P)²+0.2811P] 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         4730
_refine_ls_number_parameters     295
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0677
_refine_ls_R_factor_gt           0.0455
_refine_ls_wR_factor_ref         0.1154
_refine_ls_wR_factor_gt          0.1054
_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 0.29029(4) 0.23397(4) 0.02291(3) 0.03035(13) Uani 1 1 d . . .
N1 N 0.52297(18) 0.26587(19) 0.01073(15) 0.0289(4) Uani 1 1 d . . .
N2 N 0.33878(18) 0.08465(19) -0.10527(15) 0.0304(4) Uani 1 1 d . . .
N4 N 0.48635(19) -0.0233(2) -0.21466(16) 0.0343(4) Uani 1 1 d . . .
H4N H 0.5650 -0.0442 -0.2426 0.041 Uiso 1 1 calc R . .
O2 O 0.15928(17) 0.28541(18) -0.04692(16) 0.0468(4) Uani 1 1 d . . .
C6 C 0.4752(2) 0.0778(2) -0.12918(19) 0.0294(5) Uani 1 1 d . . .
N5 N 0.5506(2) 0.5645(2) 0.22350(17) 0.0374(5) Uani 1 1 d . . .
H5 H 0.6363 0.6049 0.2453 0.045 Uiso 1 1 calc R . .
O1 O 0.22584(18) 0.13302(18) 0.11665(15) 0.0477(5) Uani 1 1 d . . .
C1 C 0.6033(2) 0.3697(2) 0.08048(19) 0.0302(5) Uani 1 1 d . . .
C2 C 0.7524(2) 0.3879(3) 0.0803(2) 0.0356(5) Uani 1 1 d . . .
H2 H 0.8078 0.4606 0.1279 0.043 Uiso 1 1 calc R . .
C3 C 0.8170(2) 0.2961(3) 0.0080(2) 0.0369(6) Uani 1 1 d . . .
H3 H 0.9169 0.3061 0.0077 0.044 Uiso 1 1 calc R . .
C4 C 0.7338(2) 0.1889(3) -0.0643(2) 0.0340(5) Uani 1 1 d . . .
H4 H 0.7765 0.1263 -0.1129 0.041 Uiso 1 1 calc R . .
C5 C 0.5856(2) 0.1781(2) -0.06172(18) 0.0277(5) Uani 1 1 d . . .
C7 C 0.2560(2) -0.0196(2) -0.18006(19) 0.0309(5) Uani 1 1 d . . .
C12 C 0.1068(2) -0.0605(3) -0.1919(2) 0.0399(6) Uani 1 1 d . . .
H12 H 0.0446 -0.0158 -0.1456 0.048 Uiso 1 1 calc R . .
C11 C 0.0568(3) -0.1691(3) -0.2744(2) 0.0483(7) Uani 1 1 d . . .
H11 H -0.0420 -0.1989 -0.2845 0.058 Uiso 1 1 calc R . .
C10 C 0.1497(3) -0.2375(3) -0.3449(2) 0.0508(7) Uani 1 1 d . . .
H10 H 0.1111 -0.3111 -0.4002 0.061 Uiso 1 1 calc R . .
C9 C 0.2965(3) -0.1979(3) -0.3337(2) 0.0458(6) Uani 1 1 d . . .
H9 H 0.3582 -0.2428 -0.3804 0.055 Uiso 1 1 calc R . .
C8 C 0.3481(2) -0.0883(3) -0.2500(2) 0.0340(5) Uani 1 1 d . . .
C13 C 0.5121(2) 0.4529(2) 0.14914(19) 0.0311(5) Uani 1 1 d . . .
C14 C 0.4213(3) 0.6021(2) 0.25871(19) 0.0346(5) Uani 1 1 d . . .
C15 C 0.3921(3) 0.7148(3) 0.3339(2) 0.0442(6) Uani 1 1 d . . .
H15 H 0.4661 0.7781 0.3735 0.053 Uiso 1 1 calc R . .
C16 C 0.2492(3) 0.7290(3) 0.3475(2) 0.0498(7) Uani 1 1 d . . .
H16 H 0.2272 0.8042 0.3962 0.060 Uiso 1 1 calc R . .
C17 C 0.1370(3) 0.6332(3) 0.2900(2) 0.0487(7) Uani 1 1 d . . .
H17 H 0.0422 0.6466 0.3014 0.058 Uiso 1 1 calc R . .
C18 C 0.1632(3) 0.5195(3) 0.2168(2) 0.0413(6) Uani 1 1 d . . .
H18 H 0.0884 0.4551 0.1798 0.050 Uiso 1 1 calc R . .
C19 C 0.3071(2) 0.5056(2) 0.20076(19) 0.0327(5) Uani 1 1 d . . .
N3 N 0.36766(19) 0.4097(2) 0.13022(16) 0.0322(4) Uani 1 1 d . . .
O5 O 0.3325(2) 0.0932(3) 0.38230(18) 0.0687(6) Uani 1 1 d . . .
C21 C 0.3153(3) 0.2138(4) 0.4056(2) 0.0520(7) Uani 1 1 d . . .
N6 N 0.2495(2) 0.2629(2) 0.49798(18) 0.0463(5) Uani 1 1 d . . .
C20 C 0.2330(4) 0.4081(3) 0.5194(3) 0.0656(9) Uani 1 1 d . . .
H20A H 0.2844 0.4595 0.4632 0.098 Uiso 1 1 calc R . .
H20B H 0.2708 0.4442 0.5973 0.098 Uiso 1 1 calc R . .
H20C H 0.1327 0.4170 0.5121 0.098 Uiso 1 1 calc R . .
C24 C 0.1888(4) 0.1717(3) 0.5804(3) 0.0729(10) Uani 1 1 d . . .
H24A H 0.0856 0.1586 0.5707 0.109 Uiso 1 1 calc R . .
H24B H 0.2182 0.2124 0.6590 0.109 Uiso 1 1 calc R . .
H24C H 0.2222 0.0835 0.5665 0.109 Uiso 1 1 calc R . .
H51 H 0.355(3) 0.287(3) 0.359(3) 0.069(9) 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 1.6092(16) . ?
V1 O2 1.6100(17) . ?
V1 N3 2.0321(19) . ?
V1 N2 2.0746(19) . ?
V1 N1 2.1750(17) . ?
N1 C1 1.343(3) . ?
N1 C5 1.346(3) . ?
N2 C6 1.330(3) . ?
N2 C7 1.385(3) . ?
N4 C6 1.337(3) . ?
N4 C8 1.386(3) . ?
N4 H4N 0.8600 . ?
C6 C5 1.457(3) . ?
N5 C13 1.311(3) . ?
N5 C14 1.382(3) . ?
N5 H5 0.8600 . ?
C1 C2 1.386(3) . ?
C1 C13 1.462(3) . ?
C2 C3 1.380(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.390(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.382(3) . ?
C4 H4 0.9300 . ?
C7 C8 1.398(3) . ?
C7 C12 1.398(3) . ?
C12 C11 1.363(4) . ?
C12 H12 0.9300 . ?
C11 C10 1.406(4) . ?
C11 H11 0.9300 . ?
C10 C9 1.374(4) . ?
C10 H10 0.9300 . ?
C9 C8 1.381(3) . ?
C9 H9 0.9300 . ?
C13 N3 1.364(3) . ?
C14 C15 1.394(3) . ?
C14 C19 1.416(3) . ?
C15 C16 1.383(4) . ?
C15 H15 0.9300 . ?
C16 C17 1.399(4) . ?
C16 H16 0.9300 . ?
C17 C18 1.381(3) . ?
C17 H17 0.9300 . ?
C18 C19 1.395(3) . ?
C18 H18 0.9300 . ?
C19 N3 1.376(3) . ?
O5 C21 1.217(4) . ?
C21 N6 1.330(3) . ?
C21 H51 0.97(3) . ?
N6 C24 1.442(3) . ?
N6 C20 1.447(3) . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C24 H24A 0.9600 . ?
C24 H24B 0.9600 . ?
C24 H24C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 V1 O2 109.05(9) . . ?
O1 V1 N3 101.00(8) . . ?
O2 V1 N3 100.64(8) . . ?
O1 V1 N2 98.97(8) . . ?
O2 V1 N2 98.79(8) . . ?
N3 V1 N2 145.69(7) . . ?
O1 V1 N1 116.94(8) . . ?
O2 V1 N1 133.95(8) . . ?
N3 V1 N1 73.42(7) . . ?
N2 V1 N1 72.71(7) . . ?
C1 N1 C5 120.64(18) . . ?
C1 N1 V1 119.18(14) . . ?
C5 N1 V1 120.10(14) . . ?
C6 N2 C7 106.12(19) . . ?
C6 N2 V1 120.15(16) . . ?
C7 N2 V1 133.72(14) . . ?
C6 N4 C8 107.58(18) . . ?
C6 N4 H4N 126.2 . . ?
C8 N4 H4N 126.2 . . ?
N2 C6 N4 112.1(2) . . ?
N2 C6 C5 117.2(2) . . ?
N4 C6 C5 130.72(19) . . ?
C13 N5 C14 103.94(19) . . ?
C13 N5 H5 128.0 . . ?
C14 N5 H5 128.0 . . ?
N1 C1 C2 120.8(2) . . ?
N1 C1 C13 110.91(18) . . ?
C2 C1 C13 128.3(2) . . ?
C3 C2 C1 118.7(2) . . ?
C3 C2 H2 120.7 . . ?
C1 C2 H2 120.7 . . ?
C2 C3 C4 120.5(2) . . ?
C2 C3 H3 119.8 . . ?
C4 C3 H3 119.8 . . ?
C5 C4 C3 118.0(2) . . ?
C5 C4 H4 121.0 . . ?
C3 C4 H4 121.0 . . ?
N1 C5 C4 121.4(2) . . ?
N1 C5 C6 109.68(17) . . ?
C4 C5 C6 128.9(2) . . ?
N2 C7 C8 108.48(19) . . ?
N2 C7 C12 130.7(2) . . ?
C8 C7 C12 120.8(2) . . ?
C11 C12 C7 116.9(2) . . ?
C11 C12 H12 121.6 . . ?
C7 C12 H12 121.6 . . ?
C12 C11 C10 122.1(2) . . ?
C12 C11 H11 119.0 . . ?
C10 C11 H11 119.0 . . ?
C9 C10 C11 121.4(3) . . ?
C9 C10 H10 119.3 . . ?
C11 C10 H10 119.3 . . ?
C10 C9 C8 117.0(2) . . ?
C10 C9 H9 121.5 . . ?
C8 C9 H9 121.5 . . ?
C9 C8 N4 132.4(2) . . ?
C9 C8 C7 121.9(2) . . ?
N4 C8 C7 105.7(2) . . ?
N5 C13 N3 116.2(2) . . ?
N5 C13 C1 128.8(2) . . ?
N3 C13 C1 115.0(2) . . ?
N5 C14 C15 130.9(2) . . ?
N5 C14 C19 108.7(2) . . ?
C15 C14 C19 120.3(2) . . ?
C16 C15 C14 117.6(3) . . ?
C16 C15 H15 121.2 . . ?
C14 C15 H15 121.2 . . ?
C15 C16 C17 121.8(2) . . ?
C15 C16 H16 119.1 . . ?
C17 C16 H16 119.1 . . ?
C18 C17 C16 121.7(2) . . ?
C18 C17 H17 119.2 . . ?
C16 C17 H17 119.2 . . ?
C17 C18 C19 117.0(2) . . ?
C17 C18 H18 121.5 . . ?
C19 C18 H18 121.5 . . ?
N3 C19 C18 130.9(2) . . ?
N3 C19 C14 107.40(19) . . ?
C18 C19 C14 121.7(2) . . ?
C13 N3 C19 103.68(19) . . ?
C13 N3 V1 121.18(15) . . ?
C19 N3 V1 135.08(15) . . ?
O5 C21 N6 125.4(3) . . ?
O5 C21 H51 122.0(18) . . ?
N6 C21 H51 112.4(18) . . ?
C21 N6 C24 120.8(3) . . ?
C21 N6 C20 122.1(3) . . ?
C24 N6 C20 117.1(2) . . ?
N6 C20 H20A 109.5 . . ?
N6 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
N6 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
N6 C24 H24A 109.5 . . ?
N6 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
N6 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?

_diffrn_measured_fraction_theta_max 0.992
_diffrn_reflns_theta_full        27.53
_diffrn_measured_fraction_theta_full 0.992
_refine_diff_density_max         0.273
_refine_diff_density_min         -0.582
_refine_diff_density_rms         0.056
