# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2017

####################################################################### 
# 
# 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_nrp_db_06_0m
_database_code_depnum_ccdc_archive 'CCDC 1554874'
_audit_update_record             
;
2017-06-08 deposited with the CCDC.
2017-11-03 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C13 H11 N5 O5 V'
_chemical_formula_weight         368.21

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

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   'P2(1)/n  '

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   8.1102(13)
_cell_length_b                   14.443(2)
_cell_length_c                   13.425(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 105.226(2)
_cell_angle_gamma                90.00
_cell_volume                     1517.3(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    4453
_cell_measurement_theta_min      2.82
_cell_measurement_theta_max      26.29

_exptl_crystal_description       Cuboid
_exptl_crystal_colour            Green
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.14
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.612
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             748
_exptl_absorpt_coefficient_mu    0.690
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.8859
_exptl_absorpt_correction_T_max  0.9096
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            10187
_diffrn_reflns_av_R_equivalents  0.0222
_diffrn_reflns_av_sigmaI/netI    0.0213
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.11
_diffrn_reflns_theta_max         25.39
_reflns_number_total             2744
_reflns_number_gt                2331
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0286P)²+1.0443P] 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         2744
_refine_ls_number_parameters     223
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0388
_refine_ls_R_factor_gt           0.0308
_refine_ls_wR_factor_ref         0.0778
_refine_ls_wR_factor_gt          0.0730
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_restrained_S_all      1.054
_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 0.12211(4) 0.77212(2) 0.42862(3) 0.02910(12) Uani 1 1 d . . .
O1 O -0.06126(19) 0.81183(11) 0.36847(13) 0.0463(4) Uani 1 1 d . . .
O11 O 0.28944(18) 0.85227(9) 0.37777(11) 0.0344(3) Uani 1 1 d . . .
O12 O 0.5552(2) 0.88032(12) 0.37007(16) 0.0603(5) Uani 1 1 d . . .
C12 C 0.4503(3) 0.83515(14) 0.40050(17) 0.0354(5) Uani 1 1 d . . .
C13 C 0.5057(3) 0.75224(14) 0.46935(16) 0.0336(5) Uani 1 1 d . . .
C14 C 0.6634(3) 0.71034(17) 0.4973(2) 0.0489(6) Uani 1 1 d . . .
H14 H 0.7550 0.7336 0.4755 0.059 Uiso 1 1 calc R . .
C15 C 0.6808(3) 0.63234(19) 0.5591(2) 0.0614(8) Uani 1 1 d . . .
H15 H 0.7858 0.6023 0.5794 0.074 Uiso 1 1 calc R . .
C16 C 0.5431(3) 0.59861(18) 0.5912(2) 0.0576(7) Uani 1 1 d . . .
H16 H 0.5548 0.5471 0.6340 0.069 Uiso 1 1 calc R . .
C17 C 0.3878(3) 0.64352(15) 0.55781(17) 0.0383(5) Uani 1 1 d . . .
N18 N 0.3746(2) 0.71825(11) 0.49928(13) 0.0304(4) Uani 1 1 d . . .
C19 C 0.2145(3) 0.61717(16) 0.57297(18) 0.0419(5) Uani 1 1 d . . .
O19 O 0.2016(3) 0.55303(13) 0.62910(15) 0.0697(6) Uani 1 1 d . . .
O20 O 0.09025(19) 0.66744(10) 0.52116(11) 0.0364(3) Uani 1 1 d . . .
N31 N 0.1542(2) 0.85910(12) 0.55842(15) 0.0392(4) Uani 1 1 d . . .
C32 C 0.1832(3) 0.94883(16) 0.5623(2) 0.0482(6) Uani 1 1 d . . .
H32 H 0.2101 0.9825 0.5096 0.058 Uiso 1 1 calc R . .
N33 N 0.1696(3) 0.98532(15) 0.65011(19) 0.0551(6) Uani 1 1 d D . .
H33 H 0.187(4) 1.0410(13) 0.665(2) 0.066 Uiso 1 1 d D . .
C34 C 0.1335(4) 0.9163(2) 0.7073(3) 0.0749(10) Uani 1 1 d . . .
H34 H 0.1177 0.9213 0.7733 0.090 Uiso 1 1 calc R . .
C35 C 0.1245(4) 0.8386(2) 0.6516(2) 0.0704(9) Uani 1 1 d . . .
H35 H 0.1015 0.7798 0.6730 0.084 Uiso 1 1 calc R . .
N41 N 0.1340(2) 0.67015(11) 0.31813(13) 0.0341(4) Uani 1 1 d . . .
C42 C 0.0609(3) 0.58823(15) 0.30951(19) 0.0440(6) Uani 1 1 d . . .
H42 H -0.0026 0.5663 0.3530 0.053 Uiso 1 1 calc R . .
N43 N 0.0888(3) 0.54092(14) 0.23133(17) 0.0502(5) Uani 1 1 d D . .
H43 H 0.049(3) 0.4865(13) 0.212(2) 0.060 Uiso 1 1 d D . .
C44 C 0.1818(5) 0.5949(2) 0.1859(3) 0.0837(11) Uani 1 1 d . . .
H44 H 0.2200 0.5802 0.1283 0.100 Uiso 1 1 calc R . .
C45 C 0.2092(4) 0.6744(2) 0.2393(2) 0.0729(10) Uani 1 1 d . . .
H45 H 0.2705 0.7247 0.2246 0.087 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 1.6006(16) . ?
V1 O20 2.0160(14) . ?
V1 O11 2.0333(14) . ?
V1 N31 2.1080(18) . ?
V1 N41 2.1102(17) . ?
V1 N18 2.1630(17) . ?
O11 C12 1.284(3) . ?
O12 C12 1.224(3) . ?
C12 C13 1.507(3) . ?
C13 N18 1.326(3) . ?
C13 C14 1.375(3) . ?
C14 C15 1.384(3) . ?
C14 H14 0.9300 . ?
C15 C16 1.387(4) . ?
C15 H15 0.9300 . ?
C16 C17 1.382(3) . ?
C16 H16 0.9300 . ?
C17 N18 1.323(3) . ?
C17 C19 1.521(3) . ?
C19 O19 1.216(3) . ?
C19 O20 1.288(3) . ?
N31 C32 1.316(3) . ?
N31 C35 1.368(3) . ?
C32 N33 1.322(3) . ?
C32 H32 0.9300 . ?
N33 C34 1.337(4) . ?
N33 H33 0.831(17) . ?
C34 C35 1.340(4) . ?
C34 H34 0.9300 . ?
C35 H35 0.9300 . ?
N41 C42 1.315(3) . ?
N41 C45 1.355(3) . ?
C42 N43 1.321(3) . ?
C42 H42 0.9300 . ?
N43 C44 1.339(4) . ?
N43 H43 0.863(17) . ?
C44 C45 1.341(4) . ?
C44 H44 0.9300 . ?
C45 H45 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 O20 109.10(8) . . ?
O1 V1 O11 103.90(7) . . ?
O20 V1 O11 147.00(6) . . ?
O1 V1 N31 95.74(8) . . ?
O20 V1 N31 86.87(7) . . ?
O11 V1 N31 89.42(7) . . ?
O1 V1 N41 95.92(8) . . ?
O20 V1 N41 86.94(6) . . ?
O11 V1 N41 90.21(6) . . ?
N31 V1 N41 168.06(7) . . ?
O1 V1 N18 175.84(8) . . ?
O20 V1 N18 73.73(6) . . ?
O11 V1 N18 73.35(6) . . ?
N31 V1 N18 87.41(7) . . ?
N41 V1 N18 81.06(7) . . ?
C12 O11 V1 122.47(13) . . ?
O12 C12 O11 124.8(2) . . ?
O12 C12 C13 120.4(2) . . ?
O11 C12 C13 114.81(17) . . ?
N18 C13 C14 121.12(19) . . ?
N18 C13 C12 110.27(18) . . ?
C14 C13 C12 128.6(2) . . ?
C13 C14 C15 117.6(2) . . ?
C13 C14 H14 121.2 . . ?
C15 C14 H14 121.2 . . ?
C14 C15 C16 120.5(2) . . ?
C14 C15 H15 119.7 . . ?
C16 C15 H15 119.7 . . ?
C17 C16 C15 118.3(2) . . ?
C17 C16 H16 120.8 . . ?
C15 C16 H16 120.8 . . ?
N18 C17 C16 120.0(2) . . ?
N18 C17 C19 110.50(19) . . ?
C16 C17 C19 129.4(2) . . ?
C17 N18 C13 122.40(19) . . ?
C17 N18 V1 118.28(14) . . ?
C13 N18 V1 118.44(13) . . ?
O19 C19 O20 125.6(2) . . ?
O19 C19 C17 120.4(2) . . ?
O20 C19 C17 113.98(18) . . ?
C19 O20 V1 123.16(13) . . ?
C32 N31 C35 104.5(2) . . ?
C32 N31 V1 126.98(17) . . ?
C35 N31 V1 127.88(16) . . ?
N31 C32 N33 111.8(2) . . ?
N31 C32 H32 124.1 . . ?
N33 C32 H32 124.1 . . ?
C32 N33 C34 107.3(2) . . ?
C32 N33 H33 124(2) . . ?
C34 N33 H33 129(2) . . ?
N33 C34 C35 107.0(3) . . ?
N33 C34 H34 126.5 . . ?
C35 C34 H34 126.5 . . ?
C34 C35 N31 109.4(3) . . ?
C34 C35 H35 125.3 . . ?
N31 C35 H35 125.3 . . ?
C42 N41 C45 104.9(2) . . ?
C42 N41 V1 125.96(16) . . ?
C45 N41 V1 129.08(16) . . ?
N41 C42 N43 111.6(2) . . ?
N41 C42 H42 124.2 . . ?
N43 C42 H42 124.2 . . ?
C42 N43 C44 107.2(2) . . ?
C42 N43 H43 125.5(19) . . ?
C44 N43 H43 127.2(19) . . ?
N43 C44 C45 106.8(2) . . ?
N43 C44 H44 126.6 . . ?
C45 C44 H44 126.6 . . ?
C44 C45 N41 109.5(3) . . ?
C44 C45 H45 125.3 . . ?
N41 C45 H45 125.3 . . ?

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
N33 H33 O1 0.831(17) 2.35(2) 3.050(3) 142(3) 3_576
N43 H43 O12 0.863(17) 1.948(18) 2.786(3) 164(3) 2_545

_diffrn_measured_fraction_theta_max 0.984
_diffrn_reflns_theta_full        25.39
_diffrn_measured_fraction_theta_full 0.984
_refine_diff_density_max         0.236
_refine_diff_density_min         -0.234
_refine_diff_density_rms         0.043
####################################################################### 
# 
# 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_shelxl
_database_code_depnum_ccdc_archive 'CCDC 1554876'
_audit_update_record             
;
2017-06-08 deposited with the CCDC.
2017-11-03 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C19 H19 N5 O5 V'
_chemical_formula_weight         448.33

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

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                   22.8084(16)
_cell_length_b                   7.7189(5)
_cell_length_c                   23.1109(19)
_cell_angle_alpha                90.00
_cell_angle_beta                 96.434(7)
_cell_angle_gamma                90.00
_cell_volume                     4043.2(5)
_cell_formula_units_Z            8
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    13388
_cell_measurement_theta_min      3.36
_cell_measurement_theta_max      30.00

_exptl_crystal_description       needle
_exptl_crystal_colour            black
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.07

_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.473
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1848
_exptl_absorpt_coefficient_mu    0.532
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   'ABSPACK, Oxford Diffraction Ltd'
_exptl_absorpt_correction_T_min  0.934
_exptl_absorpt_correction_T_max  1.000
_exptl_special_details           
;
 
;

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

_diffrn_reflns_number            13388
_diffrn_reflns_av_R_equivalents  0.0545
_diffrn_reflns_av_sigmaI/netI    0.0782
_diffrn_reflns_limit_h_min       -32
_diffrn_reflns_limit_h_max       31
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_theta_min         3.36
_diffrn_reflns_theta_max         30.00
_reflns_number_total             5838
_reflns_number_gt                4186
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Crysalis, Oxford Diffraction'
_computing_cell_refinement       'Crysalis, Oxford Diffraction'
_computing_data_reduction        'Crysalis, Oxford Diffraction'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    PLATON(Spek,2004)
_computing_publication_material  'SHELXL-97, PLATON, WINGX (Ferrugia, 2012)'


_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)+(0.0401P)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     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         5838
_refine_ls_number_parameters     271
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0813
_refine_ls_R_factor_gt           0.0529
_refine_ls_wR_factor_ref         0.1159
_refine_ls_wR_factor_gt          0.1046
_refine_ls_goodness_of_fit_ref   1.010
_refine_ls_restrained_S_all      1.010
_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 0.342400(15) 0.42983(4) 0.100884(16) 0.01697(10) Uani 1 1 d . . .
O1 O 0.27597(7) 0.4156(2) 0.11741(7) 0.0276(4) Uani 1 1 d . . .
O11 O 0.35524(6) 0.20211(17) 0.06104(7) 0.0194(3) Uani 1 1 d . . .
C12 C 0.40503(10) 0.1613(3) 0.04143(10) 0.0199(5) Uani 1 1 d . . .
O13 O 0.41413(8) 0.03172(19) 0.01363(8) 0.0345(4) Uani 1 1 d . . .
C14 C 0.45334(9) 0.2947(2) 0.05566(9) 0.0168(4) Uani 1 1 d . . .
C15 C 0.51236(10) 0.2845(3) 0.04675(10) 0.0210(5) Uani 1 1 d . . .
H15 H 0.5272 0.1880 0.0292 0.025 Uiso 1 1 calc R . .
C16 C 0.54838(10) 0.4233(3) 0.06496(10) 0.0241(5) Uani 1 1 d . . .
H16 H 0.5881 0.4205 0.0593 0.029 Uiso 1 1 calc R . .
C17 C 0.52578(9) 0.5678(3) 0.09173(10) 0.0227(5) Uani 1 1 d . . .
H17 H 0.5499 0.6605 0.1044 0.027 Uiso 1 1 calc R . .
C18 C 0.46640(9) 0.5676(2) 0.09861(9) 0.0172(4) Uani 1 1 d . . .
N19 N 0.43240(7) 0.4332(2) 0.08066(7) 0.0145(3) Uani 1 1 d . . .
C20 C 0.43102(10) 0.7027(3) 0.12729(10) 0.0199(5) Uani 1 1 d . . .
O21 O 0.37603(7) 0.66115(18) 0.12909(7) 0.0205(3) Uani 1 1 d . . .
O22 O 0.45473(7) 0.83493(19) 0.14745(8) 0.0315(4) Uani 1 1 d . . .
N31 N 0.32088(7) 0.5418(2) 0.01802(8) 0.0177(4) Uani 1 1 d . . .
C32 C 0.32722(9) 0.7136(3) 0.00197(10) 0.0196(5) Uani 1 1 d . . .
H32 H 0.3466 0.7991 0.0252 0.023 Uiso 1 1 calc R . .
C33 C 0.30066(9) 0.7366(3) -0.05280(10) 0.0209(5) Uani 1 1 d . . .
H33 H 0.2985 0.8392 -0.0740 0.025 Uiso 1 1 calc R . .
N34 N 0.27755(7) 0.5788(2) -0.07099(8) 0.0186(4) Uani 1 1 d . . .
C35 C 0.29054(9) 0.4664(3) -0.02738(10) 0.0202(5) Uani 1 1 d . . .
H35 H 0.2797 0.3502 -0.0287 0.024 Uiso 1 1 calc R . .
C36 C 0.24141(10) 0.5439(3) -0.12657(10) 0.0253(5) Uani 1 1 d . . .
H36A H 0.2062 0.6152 -0.1292 0.030 Uiso 1 1 calc R . .
H36B H 0.2292 0.4235 -0.1277 0.030 Uiso 1 1 calc R . .
C37 C 0.27430(11) 0.5805(3) -0.17725(11) 0.0286(5) Uani 1 1 d . . .
H37 H 0.3061 0.5096 -0.1830 0.034 Uiso 1 1 calc R . .
C38 C 0.26117(13) 0.7063(4) -0.21404(12) 0.0435(7) Uani 1 1 d . . .
H38A H 0.2296 0.7793 -0.2094 0.052 Uiso 1 1 calc R . .
H38B H 0.2834 0.7230 -0.2450 0.052 Uiso 1 1 calc R . .
N41 N 0.38312(8) 0.3281(2) 0.18077(8) 0.0203(4) Uani 1 1 d . . .
C42 C 0.40134(11) 0.4178(3) 0.23124(11) 0.0311(6) Uani 1 1 d . . .
H42 H 0.4000 0.5375 0.2355 0.037 Uiso 1 1 calc R . .
C43 C 0.42128(12) 0.3059(3) 0.27316(11) 0.0358(6) Uani 1 1 d . . .
H43 H 0.4361 0.3333 0.3112 0.043 Uiso 1 1 calc R . .
N44 N 0.41568(9) 0.1436(3) 0.24949(9) 0.0277(5) Uani 1 1 d . . .
C45 C 0.39284(10) 0.1621(3) 0.19414(10) 0.0228(5) Uani 1 1 d . . .
H45 H 0.3847 0.0708 0.1682 0.027 Uiso 1 1 calc R . .
C46 C 0.42618(13) -0.0213(3) 0.28125(12) 0.0374(7) Uani 1 1 d . . .
H46A H 0.4617 -0.0117 0.3084 0.045 Uiso 1 1 calc R . .
H46B H 0.4322 -0.1132 0.2539 0.045 Uiso 1 1 calc R . .
C47 C 0.37554(13) -0.0655(3) 0.31344(14) 0.0438(7) Uani 1 1 d . . .
H47 H 0.3398 -0.0910 0.2917 0.053 Uiso 1 1 calc R . .
C48 C 0.37737(16) -0.0713(3) 0.36945(16) 0.0559(9) Uani 1 1 d . . .
H48A H 0.4124 -0.0466 0.3926 0.067 Uiso 1 1 calc R . .
H48B H 0.3437 -0.1001 0.3866 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 1.6072(15) . ?
V1 O11 2.0208(14) . ?
V1 O21 2.0222(15) . ?
V1 N31 2.1083(18) . ?
V1 N41 2.1222(19) . ?
V1 N19 2.1559(17) . ?
O11 C12 1.307(2) . ?
C12 O13 1.219(2) . ?
C12 C14 1.517(3) . ?
C14 N19 1.329(2) . ?
C14 C15 1.387(3) . ?
C15 C16 1.387(3) . ?
C15 H15 0.9300 . ?
C16 C17 1.401(3) . ?
C16 H16 0.9300 . ?
C17 C18 1.381(3) . ?
C17 H17 0.9300 . ?
C18 N19 1.333(2) . ?
C18 C20 1.516(3) . ?
C20 O22 1.222(2) . ?
C20 O21 1.300(3) . ?
N31 C35 1.325(3) . ?
N31 C32 1.389(2) . ?
C32 C33 1.352(3) . ?
C32 H32 0.9300 . ?
C33 N34 1.374(3) . ?
C33 H33 0.9300 . ?
N34 C35 1.338(3) . ?
N34 C36 1.471(3) . ?
C35 H35 0.9300 . ?
C36 C37 1.487(3) . ?
C36 H36A 0.9700 . ?
C36 H36B 0.9700 . ?
C37 C38 1.303(3) . ?
C37 H37 0.9300 . ?
C38 H38A 0.9300 . ?
C38 H38B 0.9300 . ?
N41 C45 1.330(3) . ?
N41 C42 1.380(3) . ?
C42 C43 1.339(4) . ?
C42 H42 0.9300 . ?
C43 N44 1.367(3) . ?
C43 H43 0.9300 . ?
N44 C45 1.334(3) . ?
N44 C46 1.475(3) . ?
C45 H45 0.9300 . ?
C46 C47 1.482(4) . ?
C46 H46A 0.9700 . ?
C46 H46B 0.9700 . ?
C47 C48 1.291(4) . ?
C47 H47 0.9300 . ?
C48 H48A 0.9300 . ?
C48 H48B 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 O11 103.74(7) . . ?
O1 V1 O21 108.50(7) . . ?
O11 V1 O21 147.76(6) . . ?
O1 V1 N31 96.55(8) . . ?
O11 V1 N31 88.48(6) . . ?
O21 V1 N31 88.41(6) . . ?
O1 V1 N41 95.76(8) . . ?
O11 V1 N41 90.16(6) . . ?
O21 V1 N41 86.17(7) . . ?
N31 V1 N41 167.59(7) . . ?
O1 V1 N19 176.55(7) . . ?
O11 V1 N19 73.83(6) . . ?
O21 V1 N19 73.94(6) . . ?
N31 V1 N19 85.90(7) . . ?
N41 V1 N19 81.87(7) . . ?
C12 O11 V1 122.90(13) . . ?
O13 C12 O11 125.9(2) . . ?
O13 C12 C14 120.6(2) . . ?
O11 C12 C14 113.56(17) . . ?
N19 C14 C15 120.81(19) . . ?
N19 C14 C12 110.63(17) . . ?
C15 C14 C12 128.55(19) . . ?
C14 C15 C16 117.59(19) . . ?
C14 C15 H15 121.2 . . ?
C16 C15 H15 121.2 . . ?
C15 C16 C17 120.9(2) . . ?
C15 C16 H16 119.5 . . ?
C17 C16 H16 119.5 . . ?
C18 C17 C16 117.65(19) . . ?
C18 C17 H17 121.2 . . ?
C16 C17 H17 121.2 . . ?
N19 C18 C17 120.56(19) . . ?
N19 C18 C20 110.61(18) . . ?
C17 C18 C20 128.79(19) . . ?
C14 N19 C18 122.44(18) . . ?
C14 N19 V1 118.80(13) . . ?
C18 N19 V1 118.46(13) . . ?
O22 C20 O21 125.5(2) . . ?
O22 C20 C18 120.4(2) . . ?
O21 C20 C18 114.00(17) . . ?
C20 O21 V1 122.70(13) . . ?
C35 N31 C32 105.60(18) . . ?
C35 N31 V1 125.94(14) . . ?
C32 N31 V1 127.82(15) . . ?
C33 C32 N31 109.01(19) . . ?
C33 C32 H32 125.5 . . ?
N31 C32 H32 125.5 . . ?
C32 C33 N34 106.66(18) . . ?
C32 C33 H33 126.7 . . ?
N34 C33 H33 126.7 . . ?
C35 N34 C33 107.43(18) . . ?
C35 N34 C36 126.43(18) . . ?
C33 N34 C36 125.99(18) . . ?
N31 C35 N34 111.30(18) . . ?
N31 C35 H35 124.3 . . ?
N34 C35 H35 124.3 . . ?
N34 C36 C37 111.71(19) . . ?
N34 C36 H36A 109.3 . . ?
C37 C36 H36A 109.3 . . ?
N34 C36 H36B 109.3 . . ?
C37 C36 H36B 109.3 . . ?
H36A C36 H36B 107.9 . . ?
C38 C37 C36 123.8(2) . . ?
C38 C37 H37 118.1 . . ?
C36 C37 H37 118.1 . . ?
C37 C38 H38A 120.0 . . ?
C37 C38 H38B 120.0 . . ?
H38A C38 H38B 120.0 . . ?
C45 N41 C42 105.09(19) . . ?
C45 N41 V1 127.14(15) . . ?
C42 N41 V1 127.62(15) . . ?
C43 C42 N41 109.5(2) . . ?
C43 C42 H42 125.3 . . ?
N41 C42 H42 125.3 . . ?
C42 C43 N44 107.0(2) . . ?
C42 C43 H43 126.5 . . ?
N44 C43 H43 126.5 . . ?
C45 N44 C43 107.1(2) . . ?
C45 N44 C46 126.4(2) . . ?
C43 N44 C46 126.1(2) . . ?
N41 C45 N44 111.3(2) . . ?
N41 C45 H45 124.4 . . ?
N44 C45 H45 124.4 . . ?
N44 C46 C47 110.9(2) . . ?
N44 C46 H46A 109.5 . . ?
C47 C46 H46A 109.5 . . ?
N44 C46 H46B 109.5 . . ?
C47 C46 H46B 109.5 . . ?
H46A C46 H46B 108.1 . . ?
C48 C47 C46 124.9(3) . . ?
C48 C47 H47 117.6 . . ?
C46 C47 H47 117.6 . . ?
C47 C48 H48A 120.0 . . ?
C47 C48 H48B 120.0 . . ?
H48A C48 H48B 120.0 . . ?

_diffrn_measured_fraction_theta_max 0.991
_diffrn_reflns_theta_full        30.00
_diffrn_measured_fraction_theta_full 0.991
_refine_diff_density_max         0.379
_refine_diff_density_min         -0.557
_refine_diff_density_rms         0.071
####################################################################### 
# 
# 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_shelxl_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 1554875'
_audit_update_record             
;
2017-06-08 deposited with the CCDC.
2017-11-03 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C15 H15 N5 O5 V'
_chemical_formula_weight         396.26

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

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   P-1

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

_cell_length_a                   8.8853(10)
_cell_length_b                   11.7493(9)
_cell_length_c                   16.9170(16)
_cell_angle_alpha                88.699(7)
_cell_angle_beta                 82.542(8)
_cell_angle_gamma                86.201(7)
_cell_volume                     1747.1(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    10355
_cell_measurement_theta_min      3.48
_cell_measurement_theta_max      27.50

_exptl_crystal_description       needle
_exptl_crystal_colour            black
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.06

_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.507
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             812
_exptl_absorpt_coefficient_mu    0.605

_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   'ABSPACK, Oxford Diffraction Ltd'

_exptl_absorpt_correction_T_min  0.917
_exptl_absorpt_correction_T_max  1.000


_exptl_special_details           
;
 ?
;

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

_diffrn_reflns_number            10355
_diffrn_reflns_av_R_equivalents  0.0522
_diffrn_reflns_av_sigmaI/netI    0.1310
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         3.48
_diffrn_reflns_theta_max         27.50
_reflns_number_total             7813
_reflns_number_gt                5292
_reflns_threshold_expression     >2sigma(I)



_computing_data_collection       'Crysalis, Oxford Diffraction'
_computing_cell_refinement       'Crysalis, Oxford Diffraction'
_computing_data_reduction        'Crysalis, Oxford Diffraction'
_computing_structure_solution    'SHELXS (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL (Sheldrick, 2008)'
_computing_molecular_graphics    PLATON(Spek,2004)
_computing_publication_material  'SHELXL, PLATON, WINGX (Ferrugia, 2012)'



_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)+(0.0493P)²+0.5746P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         7813
_refine_ls_number_parameters     473
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1285
_refine_ls_R_factor_gt           0.0841
_refine_ls_wR_factor_ref         0.1852
_refine_ls_wR_factor_gt          0.1602
_refine_ls_goodness_of_fit_ref   1.085
_refine_ls_restrained_S_all      1.085
_refine_ls_shift/su_max          0.002
_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 0.75719(10) 0.18520(7) 0.10535(5) 0.0198(2) Uani 1 1 d . . .
V2 V 0.74392(9) 0.29871(6) 0.62527(5) 0.0191(2) Uani 1 1 d . . .
O1A O 0.8310(4) 0.0570(3) 0.0960(2) 0.0282(8) Uani 1 1 d . . .
O11A O 0.8137(4) 0.2628(3) -0.00154(19) 0.0230(8) Uani 1 1 d . . .
O12A O 0.8053(5) 0.4195(3) -0.0804(2) 0.0349(9) Uani 1 1 d . . .
C12A C 0.7754(6) 0.3692(4) -0.0169(3) 0.0241(11) Uani 1 1 d . . .
C13A C 0.6847(6) 0.4298(4) 0.0546(3) 0.0221(11) Uani 1 1 d . . .
C14A C 0.6299(6) 0.5420(4) 0.0612(3) 0.0260(11) Uani 1 1 d . . .
H14A H 0.6476 0.5929 0.0186 0.031 Uiso 1 1 calc R . .
C15A C 0.5471(6) 0.5778(4) 0.1331(3) 0.0277(12) Uani 1 1 d . . .
H15A H 0.5067 0.6528 0.1383 0.033 Uiso 1 1 calc R . .
C16A C 0.5247(6) 0.5013(4) 0.1973(3) 0.0259(11) Uani 1 1 d . . .
H16A H 0.4702 0.5242 0.2457 0.031 Uiso 1 1 calc R . .
C17A C 0.5859(5) 0.3906(4) 0.1868(3) 0.0195(10) Uani 1 1 d . . .
N18A N 0.6633(5) 0.3592(3) 0.1166(2) 0.0195(9) Uani 1 1 d . . .
C19A C 0.5809(6) 0.2935(4) 0.2460(3) 0.0242(11) Uani 1 1 d . . .
O19A O 0.5190(5) 0.3071(3) 0.3142(2) 0.0343(9) Uani 1 1 d . . .
O20A O 0.6471(4) 0.1973(3) 0.21774(19) 0.0204(7) Uani 1 1 d . . .
N31A N 0.5438(5) 0.1523(3) 0.0711(2) 0.0206(9) Uani 1 1 d . . .
C32A C 0.4404(5) 0.0981(4) 0.1177(3) 0.0206(10) Uani 1 1 d . . .
H32A H 0.4459 0.0807 0.1712 0.025 Uiso 1 1 calc R . .
N33A N 0.3257(5) 0.0712(3) 0.0781(3) 0.0254(10) Uani 1 1 d . . .
C34A C 0.3594(6) 0.1085(4) 0.0012(3) 0.0302(13) Uani 1 1 d . . .
H34A H 0.3016 0.1016 -0.0403 0.036 Uiso 1 1 calc R . .
C35A C 0.4953(6) 0.1583(4) -0.0027(3) 0.0278(12) Uani 1 1 d . . .
H35A H 0.5466 0.1909 -0.0481 0.033 Uiso 1 1 calc R . .
C36A C 0.1975(6) 0.0060(5) 0.1103(4) 0.0434(16) Uani 1 1 d . . .
H36A H 0.1920 0.0014 0.1673 0.065 Uiso 1 1 calc R . .
H36B H 0.2108 -0.0694 0.0888 0.065 Uiso 1 1 calc R . .
H36C H 0.1052 0.0431 0.0959 0.065 Uiso 1 1 calc R . .
N41A N 0.9417(5) 0.2529(3) 0.1529(3) 0.0242(10) Uani 1 1 d . . .
C42A C 0.9685(6) 0.2375(4) 0.2278(3) 0.0252(11) Uani 1 1 d . . .
H42A H 0.9131 0.1917 0.2649 0.030 Uiso 1 1 calc R . .
N43A N 1.0852(5) 0.2957(3) 0.2434(3) 0.0275(10) Uani 1 1 d . . .
C44A C 1.1344(7) 0.3548(5) 0.1748(4) 0.0390(15) Uani 1 1 d . . .
H44A H 1.2133 0.4038 0.1677 0.047 Uiso 1 1 calc R . .
C45A C 1.0460(6) 0.3278(5) 0.1200(3) 0.0339(14) Uani 1 1 d . . .
H45A H 1.0541 0.3556 0.0678 0.041 Uiso 1 1 calc R . .
C46A C 1.1434(7) 0.2999(5) 0.3211(3) 0.0385(15) Uani 1 1 d . . .
H46A H 1.1333 0.3770 0.3396 0.058 Uiso 1 1 calc R . .
H46B H 1.2486 0.2731 0.3152 0.058 Uiso 1 1 calc R . .
H46C H 1.0860 0.2522 0.3591 0.058 Uiso 1 1 calc R . .
O1B O 0.7833(4) 0.4274(3) 0.6378(2) 0.0269(8) Uani 1 1 d . . .
O11B O 0.8593(4) 0.2496(3) 0.5187(2) 0.0243(8) Uani 1 1 d . . .
O12B O 0.9122(5) 0.1170(3) 0.4231(2) 0.0401(10) Uani 1 1 d . . .
C12B C 0.8497(6) 0.1508(4) 0.4883(3) 0.0256(11) Uani 1 1 d . . .
C13B C 0.7455(6) 0.0747(4) 0.5403(3) 0.0236(11) Uani 1 1 d . . .
C14B C 0.7040(6) -0.0329(4) 0.5253(3) 0.0278(12) Uani 1 1 d . . .
H14B H 0.7438 -0.0704 0.4786 0.033 Uiso 1 1 calc R . .
C15B C 0.6009(7) -0.0839(4) 0.5819(3) 0.0332(13) Uani 1 1 d . . .
H15B H 0.5708 -0.1562 0.5726 0.040 Uiso 1 1 calc R . .
C16B C 0.5418(6) -0.0287(4) 0.6521(3) 0.0280(12) Uani 1 1 d . . .
H16B H 0.4727 -0.0628 0.6899 0.034 Uiso 1 1 calc R . .
C17B C 0.5897(5) 0.0794(4) 0.6637(3) 0.0207(10) Uani 1 1 d . . .
N18B N 0.6891(4) 0.1264(3) 0.6087(2) 0.0200(9) Uani 1 1 d . . .
C19B C 0.5440(6) 0.1583(4) 0.7331(3) 0.0213(10) Uani 1 1 d . . .
O20B O 0.5983(4) 0.2582(3) 0.72220(19) 0.0231(8) Uani 1 1 d . . .
O21B O 0.4615(4) 0.1279(3) 0.7926(2) 0.0338(9) Uani 1 1 d . . .
N31B N 0.5473(5) 0.3396(3) 0.5683(2) 0.0204(9) Uani 1 1 d . . .
C35B C 0.5372(6) 0.3499(4) 0.4883(3) 0.0226(11) Uani 1 1 d . . .
H35B H 0.6165 0.3340 0.4477 0.027 Uiso 1 1 calc R . .
C34B C 0.3930(6) 0.3869(4) 0.4774(3) 0.0241(11) Uani 1 1 d . . .
H34B H 0.3558 0.4011 0.4290 0.029 Uiso 1 1 calc R . .
N33B N 0.3138(5) 0.3990(3) 0.5518(3) 0.0253(10) Uani 1 1 d . . .
C32B C 0.4097(5) 0.3705(4) 0.6047(3) 0.0234(11) Uani 1 1 d . . .
H32B H 0.3836 0.3722 0.6598 0.028 Uiso 1 1 calc R . .
C36B C 0.1508(6) 0.4396(5) 0.5702(4) 0.0437(16) Uani 1 1 d . . .
H36D H 0.1203 0.4339 0.6267 0.066 Uiso 1 1 calc R . .
H36E H 0.0895 0.3933 0.5429 0.066 Uiso 1 1 calc R . .
H36F H 0.1377 0.5176 0.5530 0.066 Uiso 1 1 calc R . .
N41B N 0.9181(5) 0.2256(3) 0.6882(2) 0.0230(9) Uani 1 1 d . . .
N43B N 1.0577(5) 0.2086(4) 0.7863(3) 0.0269(10) Uani 1 1 d . . .
C45B C 1.0160(6) 0.1276(4) 0.6764(3) 0.0306(12) Uani 1 1 d . . .
H45B H 1.0219 0.0780 0.6339 0.037 Uiso 1 1 calc R . .
C44B C 1.1015(6) 0.1169(4) 0.7379(3) 0.0313(13) Uani 1 1 d . . .
H44B H 1.1749 0.0589 0.7454 0.038 Uiso 1 1 calc R . .
C42B C 0.9476(6) 0.2695(4) 0.7554(3) 0.0267(12) Uani 1 1 d . . .
H42B H 0.8974 0.3351 0.7783 0.032 Uiso 1 1 calc R . .
C46B C 1.1153(6) 0.2324(5) 0.8607(3) 0.0341(13) Uani 1 1 d . . .
H46D H 1.0856 0.3097 0.8757 0.051 Uiso 1 1 calc R . .
H46E H 1.2242 0.2217 0.8535 0.051 Uiso 1 1 calc R . .
H46F H 1.0740 0.1814 0.9018 0.051 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 O1A 1.605(3) . ?
V1 O11A 2.026(3) . ?
V1 O20A 2.026(3) . ?
V1 N31A 2.114(4) . ?
V1 N41A 2.124(4) . ?
V1 N18A 2.159(4) . ?
V2 O1B 1.599(3) . ?
V2 O20B 2.021(3) . ?
V2 O11B 2.031(3) . ?
V2 N41B 2.115(4) . ?
V2 N31B 2.125(4) . ?
V2 N18B 2.146(4) . ?
O11A C12A 1.303(5) . ?
O12A C12A 1.221(6) . ?
C12A C13A 1.526(7) . ?
C13A N18A 1.326(6) . ?
C13A C14A 1.376(6) . ?
C14A C15A 1.396(7) . ?
C14A H14A 0.9300 . ?
C15A C16A 1.397(7) . ?
C15A H15A 0.9300 . ?
C16A C17A 1.382(6) . ?
C16A H16A 0.9300 . ?
C17A N18A 1.339(6) . ?
C17A C19A 1.501(6) . ?
C19A O19A 1.220(6) . ?
C19A O20A 1.310(6) . ?
N31A C32A 1.317(6) . ?
N31A C35A 1.371(6) . ?
C32A N33A 1.348(6) . ?
C32A H32A 0.9300 . ?
N33A C34A 1.365(7) . ?
N33A C36A 1.454(6) . ?
C34A C35A 1.370(7) . ?
C34A H34A 0.9300 . ?
C35A H35A 0.9300 . ?
C36A H36A 0.9600 . ?
C36A H36B 0.9600 . ?
C36A H36C 0.9600 . ?
N41A C42A 1.325(6) . ?
N41A C45A 1.377(6) . ?
C42A N43A 1.336(6) . ?
C42A H42A 0.9300 . ?
N43A C44A 1.374(6) . ?
N43A C46A 1.478(6) . ?
C44A C45A 1.347(8) . ?
C44A H44A 0.9300 . ?
C45A H45A 0.9300 . ?
C46A H46A 0.9600 . ?
C46A H46B 0.9600 . ?
C46A H46C 0.9600 . ?
O11B C12B 1.292(6) . ?
O12B C12B 1.232(6) . ?
C12B C13B 1.514(7) . ?
C13B N18B 1.342(6) . ?
C13B C14B 1.378(6) . ?
C14B C15B 1.391(7) . ?
C14B H14B 0.9300 . ?
C15B C16B 1.391(7) . ?
C15B H15B 0.9300 . ?
C16B C17B 1.392(6) . ?
C16B H16B 0.9300 . ?
C17B N18B 1.334(6) . ?
C17B C19B 1.509(7) . ?
C19B O21B 1.227(6) . ?
C19B O20B 1.299(5) . ?
N31B C32B 1.327(6) . ?
N31B C35B 1.371(6) . ?
C35B C34B 1.359(7) . ?
C35B H35B 0.9300 . ?
C34B N33B 1.366(6) . ?
C34B H34B 0.9300 . ?
N33B C32B 1.337(6) . ?
N33B C36B 1.490(7) . ?
C32B H32B 0.9300 . ?
C36B H36D 0.9600 . ?
C36B H36E 0.9600 . ?
C36B H36F 0.9600 . ?
N41B C42B 1.324(6) . ?
N41B C45B 1.398(6) . ?
N43B C42B 1.328(6) . ?
N43B C44B 1.374(7) . ?
N43B C46B 1.457(6) . ?
C45B C44B 1.363(7) . ?
C45B H45B 0.9300 . ?
C44B H44B 0.9300 . ?
C42B H42B 0.9300 . ?
C46B H46D 0.9600 . ?
C46B H46E 0.9600 . ?
C46B H46F 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
O1A V1 O11A 105.57(17) . . ?
O1A V1 O20A 106.74(16) . . ?
O11A V1 O20A 147.68(13) . . ?
O1A V1 N31A 96.51(16) . . ?
O11A V1 N31A 89.65(15) . . ?
O20A V1 N31A 86.08(15) . . ?
O1A V1 N41A 96.32(17) . . ?
O11A V1 N41A 91.74(15) . . ?
O20A V1 N41A 85.43(15) . . ?
N31A V1 N41A 166.22(16) . . ?
O1A V1 N18A 178.56(17) . . ?
O11A V1 N18A 73.45(14) . . ?
O20A V1 N18A 74.26(14) . . ?
N31A V1 N18A 84.58(15) . . ?
N41A V1 N18A 82.69(15) . . ?
O1B V2 O20B 105.64(16) . . ?
O1B V2 O11B 106.57(16) . . ?
O20B V2 O11B 147.78(13) . . ?
O1B V2 N41B 94.63(17) . . ?
O20B V2 N41B 86.19(15) . . ?
O11B V2 N41B 92.04(15) . . ?
O1B V2 N31B 96.37(16) . . ?
O20B V2 N31B 86.20(15) . . ?
O11B V2 N31B 89.45(15) . . ?
N41B V2 N31B 167.99(15) . . ?
O1B V2 N18B 179.53(18) . . ?
O20B V2 N18B 74.02(14) . . ?
O11B V2 N18B 73.76(14) . . ?
N41B V2 N18B 85.69(15) . . ?
N31B V2 N18B 83.29(15) . . ?
C12A O11A V1 123.7(3) . . ?
O12A C12A O11A 126.2(5) . . ?
O12A C12A C13A 120.9(4) . . ?
O11A C12A C13A 112.8(4) . . ?
N18A C13A C14A 120.1(5) . . ?
N18A C13A C12A 110.9(4) . . ?
C14A C13A C12A 129.1(4) . . ?
C13A C14A C15A 118.7(4) . . ?
C13A C14A H14A 120.7 . . ?
C15A C14A H14A 120.7 . . ?
C16A C15A C14A 120.1(5) . . ?
C16A C15A H15A 119.9 . . ?
C14A C15A H15A 119.9 . . ?
C17A C16A C15A 117.9(5) . . ?
C17A C16A H16A 121.0 . . ?
C15A C16A H16A 121.0 . . ?
N18A C17A C16A 120.2(4) . . ?
N18A C17A C19A 111.3(4) . . ?
C16A C17A C19A 128.5(5) . . ?
C13A N18A C17A 123.0(4) . . ?
C13A N18A V1 119.1(3) . . ?
C17A N18A V1 117.9(3) . . ?
O19A C19A O20A 125.0(5) . . ?
O19A C19A C17A 120.6(5) . . ?
O20A C19A C17A 114.3(4) . . ?
C19A O20A V1 122.1(3) . . ?
C32A N31A C35A 105.9(4) . . ?
C32A N31A V1 122.9(3) . . ?
C35A N31A V1 130.0(3) . . ?
N31A C32A N33A 111.6(4) . . ?
N31A C32A H32A 124.2 . . ?
N33A C32A H32A 124.2 . . ?
C32A N33A C34A 107.0(4) . . ?
C32A N33A C36A 125.9(5) . . ?
C34A N33A C36A 126.9(5) . . ?
N33A C34A C35A 106.3(5) . . ?
N33A C34A H34A 126.8 . . ?
C35A C34A H34A 126.8 . . ?
N31A C35A C34A 109.2(5) . . ?
N31A C35A H35A 125.4 . . ?
C34A C35A H35A 125.4 . . ?
N33A C36A H36A 109.5 . . ?
N33A C36A H36B 109.5 . . ?
H36A C36A H36B 109.5 . . ?
N33A C36A H36C 109.5 . . ?
H36A C36A H36C 109.5 . . ?
H36B C36A H36C 109.5 . . ?
C42A N41A C45A 105.2(4) . . ?
C42A N41A V1 124.0(3) . . ?
C45A N41A V1 130.5(4) . . ?
N41A C42A N43A 111.6(4) . . ?
N41A C42A H42A 124.2 . . ?
N43A C42A H42A 124.2 . . ?
C42A N43A C44A 107.0(4) . . ?
C42A N43A C46A 125.9(4) . . ?
C44A N43A C46A 127.0(4) . . ?
C45A C44A N43A 106.5(5) . . ?
C45A C44A H44A 126.8 . . ?
N43A C44A H44A 126.8 . . ?
C44A C45A N41A 109.7(5) . . ?
C44A C45A H45A 125.1 . . ?
N41A C45A H45A 125.1 . . ?
N43A C46A H46A 109.5 . . ?
N43A C46A H46B 109.5 . . ?
H46A C46A H46B 109.5 . . ?
N43A C46A H46C 109.5 . . ?
H46A C46A H46C 109.5 . . ?
H46B C46A H46C 109.5 . . ?
C12B O11B V2 123.2(3) . . ?
O12B C12B O11B 126.6(5) . . ?
O12B C12B C13B 119.8(5) . . ?
O11B C12B C13B 113.5(4) . . ?
N18B C13B C14B 120.0(5) . . ?
N18B C13B C12B 110.8(4) . . ?
C14B C13B C12B 129.1(5) . . ?
C13B C14B C15B 118.1(5) . . ?
C13B C14B H14B 120.9 . . ?
C15B C14B H14B 120.9 . . ?
C16B C15B C14B 121.2(5) . . ?
C16B C15B H15B 119.4 . . ?
C14B C15B H15B 119.4 . . ?
C15B C16B C17B 117.6(5) . . ?
C15B C16B H16B 121.2 . . ?
C17B C16B H16B 121.2 . . ?
N18B C17B C16B 120.1(5) . . ?
N18B C17B C19B 111.0(4) . . ?
C16B C17B C19B 129.0(5) . . ?
C17B N18B C13B 122.9(4) . . ?
C17B N18B V2 118.3(3) . . ?
C13B N18B V2 118.5(3) . . ?
O21B C19B O20B 125.2(5) . . ?
O21B C19B C17B 121.2(4) . . ?
O20B C19B C17B 113.6(4) . . ?
C19B O20B V2 122.8(3) . . ?
C32B N31B C35B 105.8(4) . . ?
C32B N31B V2 125.7(3) . . ?
C35B N31B V2 128.2(3) . . ?
C34B C35B N31B 109.3(5) . . ?
C34B C35B H35B 125.3 . . ?
N31B C35B H35B 125.3 . . ?
C35B C34B N33B 106.3(4) . . ?
C35B C34B H34B 126.9 . . ?
N33B C34B H34B 126.9 . . ?
C32B N33B C34B 107.7(4) . . ?
C32B N33B C36B 126.4(5) . . ?
C34B N33B C36B 125.9(5) . . ?
N31B C32B N33B 111.0(5) . . ?
N31B C32B H32B 124.5 . . ?
N33B C32B H32B 124.5 . . ?
N33B C36B H36D 109.5 . . ?
N33B C36B H36E 109.5 . . ?
H36D C36B H36E 109.5 . . ?
N33B C36B H36F 109.5 . . ?
H36D C36B H36F 109.5 . . ?
H36E C36B H36F 109.5 . . ?
C42B N41B C45B 105.4(4) . . ?
C42B N41B V2 121.6(3) . . ?
C45B N41B V2 132.9(4) . . ?
C42B N43B C44B 107.8(4) . . ?
C42B N43B C46B 125.7(5) . . ?
C44B N43B C46B 126.5(4) . . ?
C44B C45B N41B 108.5(5) . . ?
C44B C45B H45B 125.7 . . ?
N41B C45B H45B 125.7 . . ?
C45B C44B N43B 106.5(4) . . ?
C45B C44B H44B 126.8 . . ?
N43B C44B H44B 126.8 . . ?
N41B C42B N43B 111.8(5) . . ?
N41B C42B H42B 124.1 . . ?
N43B C42B H42B 124.1 . . ?
N43B C46B H46D 109.5 . . ?
N43B C46B H46E 109.5 . . ?
H46D C46B H46E 109.5 . . ?
N43B C46B H46F 109.5 . . ?
H46D C46B H46F 109.5 . . ?
H46E C46B H46F 109.5 . . ?

_diffrn_measured_fraction_theta_max 0.973
_diffrn_reflns_theta_full        27.50
_diffrn_measured_fraction_theta_full 0.973
_refine_diff_density_max         1.037
_refine_diff_density_min         -0.471
_refine_diff_density_rms         0.098
