# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2018

####################################################################### 
# 
# 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_a01
_database_code_depnum_ccdc_archive 'CCDC 1823371'
_audit_update_record             
;
2018-03-22 deposited with the CCDC.
2018-03-29 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H40 N4 O20 V4'
_chemical_formula_weight         860.32

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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           20
_space_group_name_H-M_alt        'C 2 2 21'
_space_group_name_Hall           'C 2c 2'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   9.904(3)
_cell_length_b                   14.855(5)
_cell_length_c                   21.600(7)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3177.9(17)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    3036
_cell_measurement_theta_min      2.47
_cell_measurement_theta_max      25.98

_exptl_crystal_description       block
_exptl_crystal_colour            yellowish-brown
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.798
_exptl_crystal_F_000             1760
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.150
_exptl_crystal_size_mid          0.130
_exptl_crystal_size_min          0.120
_exptl_absorpt_coefficient_mu    1.231
_shelx_estimated_absorpt_T_min   0.837
_shelx_estimated_absorpt_T_max   0.866
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.837
_exptl_absorpt_correction_T_max  0.866
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2003)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker Apex2 CCD'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            11562
_diffrn_reflns_av_unetI/netI     0.0675
_diffrn_reflns_av_R_equivalents  0.0719
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         1.886
_diffrn_reflns_theta_max         26.853
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.943
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.943
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.917
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             3146
_reflns_number_gt                2697
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.731
_reflns_Friedel_fraction_max     0.884
_reflns_Friedel_fraction_full    0.997

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'APEX2 (Bruker, 2005)'
_computing_cell_refinement       'SAINT (Bruker, 2005)'
_computing_data_reduction        SAINT
_computing_structure_solution    'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    SHELXTL
_computing_publication_material  SHELXTL
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1104P)²+14.6136P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 963 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.03(2)
_chemical_absolute_configuration D
_refine_ls_number_reflns         3146
_refine_ls_number_parameters     218
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0858
_refine_ls_R_factor_gt           0.0749
_refine_ls_wR_factor_ref         0.2008
_refine_ls_wR_factor_gt          0.1937
_refine_ls_goodness_of_fit_ref   1.115
_refine_ls_restrained_S_all      1.115
_refine_ls_shift/su_max          0.004
_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
V1 V 0.13712(18) 0.76660(10) 0.20961(8) 0.0258(4) Uani 1 1 d . . . . .
V2 V 0.13503(19) 0.91176(10) 0.30644(8) 0.0286(5) Uani 1 1 d . . . . .
O1 O 0.2252(7) 0.8108(5) 0.2746(3) 0.0292(17) Uani 1 1 d . . . . .
O2 O 0.0128(8) 0.7935(5) 0.1434(3) 0.0298(16) Uani 1 1 d . . . . .
O3 O 0.2608(9) 0.9157(6) 0.0611(4) 0.041(2) Uani 1 1 d . . . . .
O4 O -0.2458(8) 0.8768(6) 0.1175(4) 0.0377(19) Uani 1 1 d . . . . .
O5 O 0.0000 0.8963(6) 0.2500 0.028(2) Uani 1 2 d S T P . .
O6 O 0.2147(9) 0.9935(6) 0.2772(4) 0.041(2) Uani 1 1 d . . . . .
O7 O -0.0419(8) 0.9691(5) 0.1303(4) 0.0349(18) Uani 1 1 d . . . . .
O11 O 0.2251(8) 0.6826(5) 0.1874(4) 0.0373(19) Uani 1 1 d . . . . .
O8 O 0.2439(7) 0.8581(5) 0.1562(4) 0.0309(17) Uani 1 1 d . . . . .
O9 O 0.0000 0.7114(6) 0.2500 0.027(2) Uani 1 2 d S T P . .
O10 O -0.2152(11) 0.8480(9) 0.0175(4) 0.069(3) Uani 1 1 d . . . . .
N1 N 0.1172(9) 1.2088(6) 0.1251(4) 0.035(2) Uani 1 1 d . . . . .
H1A H 0.1738 1.2601 0.1369 0.042 Uiso 1 1 calc R U . . .
N2 N 0.4111(9) 1.0466(6) 0.1149(5) 0.036(2) Uani 1 1 d . . . . .
H2B H 0.3605 0.9977 0.0951 0.043 Uiso 1 1 calc R U . . .
C1 C -0.1780(12) 0.8770(8) 0.0670(5) 0.037(3) Uani 1 1 d . . . . .
C2 C -0.0369(12) 0.9159(8) 0.0769(5) 0.035(3) Uani 1 1 d . . . . .
H2A H -0.0067 0.9507 0.0409 0.042 Uiso 1 1 calc R U . . .
C3 C 0.0582(11) 0.8366(7) 0.0904(5) 0.030(2) Uani 1 1 d . . . . .
H3A H 0.0594 0.7947 0.0554 0.036 Uiso 1 1 calc R U . . .
C4 C 0.1978(13) 0.8724(7) 0.1026(5) 0.033(3) Uani 1 1 d . . . . .
C5 C 0.4959(14) 1.0050(9) 0.1654(8) 0.055(4) Uani 1 1 d . . . . .
H5A H 0.4379 0.9790 0.1962 0.083 Uiso 1 1 calc R U . . .
H5B H 0.5525 0.9590 0.1481 0.083 Uiso 1 1 calc R U . . .
H5C H 0.5512 1.0506 0.1841 0.083 Uiso 1 1 calc R U . . .
C6 C 0.4988(15) 1.0870(9) 0.0670(7) 0.053(3) Uani 1 1 d . . . . .
H6A H 0.5603 1.0423 0.0517 0.080 Uiso 1 1 calc R U . . .
H6B H 0.4441 1.1089 0.0335 0.080 Uiso 1 1 calc R U . . .
H6C H 0.5489 1.1360 0.0846 0.080 Uiso 1 1 calc R U . . .
C7 C 0.0165(15) 1.2403(11) 0.0790(7) 0.060(4) Uani 1 1 d . . . . .
H7A H -0.0403 1.2853 0.0975 0.090 Uiso 1 1 calc R U . . .
H7B H 0.0625 1.2657 0.0439 0.090 Uiso 1 1 calc R U . . .
H7C H -0.0379 1.1904 0.0657 0.090 Uiso 1 1 calc R U . . .
C8 C 0.0430(13) 1.1776(10) 0.1814(6) 0.049(3) Uani 1 1 d . . . . .
H8A H -0.0118 1.2259 0.1970 0.074 Uiso 1 1 calc R U . . .
H8B H -0.0137 1.1275 0.1707 0.074 Uiso 1 1 calc R U . . .
H8C H 0.1066 1.1595 0.2125 0.074 Uiso 1 1 calc R U . . .
C9 C 0.2054(13) 1.1392(8) 0.0970(6) 0.043(3) Uani 1 1 d . . . . .
H9A H 0.2491 1.1636 0.0604 0.052 Uiso 1 1 calc R U . . .
H9B H 0.1513 1.0880 0.0843 0.052 Uiso 1 1 calc R U . . .
C10 C 0.3102(13) 1.1094(8) 0.1426(6) 0.039(3) Uani 1 1 d . . . . .
H10A H 0.3569 1.1620 0.1585 0.047 Uiso 1 1 calc R U . . .
H10B H 0.2660 1.0799 0.1771 0.047 Uiso 1 1 calc R U . . .


_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 O11 1.596(7) . ?
V1 O1 1.778(7) . ?
V1 O9 1.810(4) . ?
V1 O2 1.929(7) . ?
V1 O8 2.073(7) . ?
V2 O6 1.580(8) . ?
V2 O5 1.824(2) . ?
V2 O7 1.855(8) 3 ?
V2 O1 1.876(8) . ?
V2 O4 2.042(8) 3 ?
O2 C3 1.387(13) . ?
O3 C4 1.267(13) . ?
O4 C1 1.282(14) . ?
O4 V2 2.042(8) 3 ?
O5 V2 1.824(2) 3 ?
O7 C2 1.399(14) . ?
O7 V2 1.855(8) 3 ?
O8 C4 1.262(14) . ?
O9 V1 1.810(4) 3 ?
O10 C1 1.210(15) . ?
N1 C9 1.483(14) . ?
N1 C7 1.487(16) . ?
N1 C8 1.493(16) . ?
N1 H1A 0.9800 . ?
N2 C6 1.479(16) . ?
N2 C10 1.493(14) . ?
N2 C5 1.509(16) . ?
N2 H2B 0.9800 . ?
C1 C2 1.527(17) . ?
C2 C3 1.536(15) . ?
C2 H2A 0.9800 . ?
C3 C4 1.505(15) . ?
C3 H3A 0.9800 . ?
C5 H5A 0.9600 . ?
C5 H5B 0.9600 . ?
C5 H5C 0.9600 . ?
C6 H6A 0.9600 . ?
C6 H6B 0.9600 . ?
C6 H6C 0.9600 . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C9 C10 1.498(17) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?

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
O11 V1 O1 105.0(4) . . ?
O11 V1 O9 101.5(4) . . ?
O1 V1 O9 98.9(3) . . ?
O11 V1 O2 106.7(4) . . ?
O1 V1 O2 145.2(3) . . ?
O9 V1 O2 88.4(2) . . ?
O11 V1 O8 93.9(4) . . ?
O1 V1 O8 86.9(3) . . ?
O9 V1 O8 161.4(3) . . ?
O2 V1 O8 77.1(3) . . ?
O6 V2 O5 101.3(4) . . ?
O6 V2 O7 101.0(4) . 3 ?
O5 V2 O7 100.7(3) . 3 ?
O6 V2 O1 103.3(4) . . ?
O5 V2 O1 90.2(3) . . ?
O7 V2 O1 150.9(3) 3 . ?
O6 V2 O4 104.4(4) . 3 ?
O5 V2 O4 154.1(3) . 3 ?
O7 V2 O4 78.0(3) 3 3 ?
O1 V2 O4 80.6(3) . 3 ?
V1 O1 V2 110.6(4) . . ?
C3 O2 V1 120.1(7) . . ?
C1 O4 V2 113.8(7) . 3 ?
V2 O5 V2 165.6(6) 3 . ?
C2 O7 V2 111.5(7) . 3 ?
C4 O8 V1 115.9(6) . . ?
V1 O9 V1 126.1(5) . 3 ?
C9 N1 C7 109.9(10) . . ?
C9 N1 C8 114.1(10) . . ?
C7 N1 C8 108.2(10) . . ?
C9 N1 H1A 108.2 . . ?
C7 N1 H1A 108.2 . . ?
C8 N1 H1A 108.2 . . ?
C6 N2 C10 114.8(10) . . ?
C6 N2 C5 110.2(10) . . ?
C10 N2 C5 109.8(10) . . ?
C6 N2 H2B 107.2 . . ?
C10 N2 H2B 107.2 . . ?
C5 N2 H2B 107.2 . . ?
O10 C1 O4 126.3(12) . . ?
O10 C1 C2 122.5(11) . . ?
O4 C1 C2 111.1(10) . . ?
O7 C2 C1 107.3(9) . . ?
O7 C2 C3 107.3(9) . . ?
C1 C2 C3 107.3(9) . . ?
O7 C2 H2A 111.6 . . ?
C1 C2 H2A 111.6 . . ?
C3 C2 H2A 111.6 . . ?
O2 C3 C4 108.4(9) . . ?
O2 C3 C2 108.2(9) . . ?
C4 C3 C2 109.0(9) . . ?
O2 C3 H3A 110.4 . . ?
C4 C3 H3A 110.4 . . ?
C2 C3 H3A 110.4 . . ?
O8 C4 O3 123.8(11) . . ?
O8 C4 C3 115.7(9) . . ?
O3 C4 C3 120.5(11) . . ?
N2 C5 H5A 109.5 . . ?
N2 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
N2 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
N2 C6 H6A 109.5 . . ?
N2 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
N2 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
N1 C7 H7A 109.5 . . ?
N1 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
N1 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
N1 C8 H8A 109.5 . . ?
N1 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
N1 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
N1 C9 C10 110.1(10) . . ?
N1 C9 H9A 109.6 . . ?
C10 C9 H9A 109.6 . . ?
N1 C9 H9B 109.6 . . ?
C10 C9 H9B 109.6 . . ?
H9A C9 H9B 108.2 . . ?
N2 C10 C9 112.6(10) . . ?
N2 C10 H10A 109.1 . . ?
C9 C10 H10A 109.1 . . ?
N2 C10 H10B 109.1 . . ?
C9 C10 H10B 109.1 . . ?
H10A C10 H10B 107.8 . . ?

_refine_diff_density_max         1.709
_refine_diff_density_min         -0.955
_refine_diff_density_rms         0.144

####################################################################### 
# 
# 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_a01_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 1823372'
_audit_update_record             
;
2018-03-22 deposited with the CCDC.
2018-03-29 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H40 N4 O20 V4'
_chemical_formula_weight         860.32

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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           20
_space_group_name_H-M_alt        'C 2 2 21'
_space_group_name_Hall           'C 2c 2'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   9.9327(10)
_cell_length_b                   14.9115(14)
_cell_length_c                   21.658(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3207.8(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    2799
_cell_measurement_theta_min      2.48
_cell_measurement_theta_max      23.96

_exptl_crystal_description       Block
_exptl_crystal_colour            yellowish-brown
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.781
_exptl_crystal_F_000             1760
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.150
_exptl_crystal_size_mid          0.130
_exptl_crystal_size_min          0.120
_exptl_absorpt_coefficient_mu    1.220
_shelx_estimated_absorpt_T_min   0.838
_shelx_estimated_absorpt_T_max   0.867
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.838
_exptl_absorpt_correction_T_max  0.867
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2003)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker Apex2 CCD'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            12092
_diffrn_reflns_av_unetI/netI     0.0494
_diffrn_reflns_av_R_equivalents  0.0560
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         1.881
_diffrn_reflns_theta_max         26.918
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.949
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.949
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.921
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             3205
_reflns_number_gt                2765
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.730
_reflns_Friedel_fraction_max     0.885
_reflns_Friedel_fraction_full    0.998

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'APEX2 (Bruker, 2005)'
_computing_cell_refinement       'SAINT (Bruker, 2005)'
_computing_data_reduction        SAINT
_computing_structure_solution    'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    SHELXTL
_computing_publication_material  SHELXTL
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0370P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 1042 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.038(16)
_chemical_absolute_configuration L
_refine_ls_number_reflns         3205
_refine_ls_number_parameters     218
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0446
_refine_ls_R_factor_gt           0.0339
_refine_ls_wR_factor_ref         0.0743
_refine_ls_wR_factor_gt          0.0703
_refine_ls_goodness_of_fit_ref   0.992
_refine_ls_restrained_S_all      0.992
_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
V1 V 0.13730(7) 0.26682(5) 0.29030(3) 0.02579(18) Uani 1 1 d . . . . .
V2 V 0.13509(8) 0.41197(5) 0.19347(3) 0.02804(19) Uani 1 1 d . . . . .
O11 O 0.2247(3) 0.3114(2) 0.22522(13) 0.0292(7) Uani 1 1 d . . . . .
O10 O 0.0000 0.3971(3) 0.2500 0.0300(10) Uani 1 2 d S T P . .
O3 O -0.2463(3) 0.3767(2) 0.38231(15) 0.0374(8) Uani 1 1 d . . . . .
O9 O 0.0115(3) 0.29377(18) 0.35648(13) 0.0275(7) Uani 1 1 d . . . . .
O8 O 0.2153(3) 0.4937(2) 0.22269(15) 0.0412(8) Uani 1 1 d . . . . .
O4 O 0.2599(3) 0.4158(2) 0.43834(15) 0.0391(8) Uani 1 1 d . . . . .
O5 O -0.0419(3) 0.4691(2) 0.36982(14) 0.0351(8) Uani 1 1 d . . . . .
O7 O 0.0000 0.2115(2) 0.2500 0.0260(9) Uani 1 2 d S T P . .
O6 O 0.2235(3) 0.1828(2) 0.31305(15) 0.0376(8) Uani 1 1 d . . . . .
O2 O 0.2443(3) 0.3574(2) 0.34370(14) 0.0348(8) Uani 1 1 d . . . . .
C4 C 0.1986(5) 0.3733(3) 0.3974(2) 0.0290(10) Uani 1 1 d . . . . .
N2 N -0.3838(4) 0.2080(2) 0.37459(16) 0.0357(9) Uani 1 1 d . . . . .
H2B H -0.3280 0.2594 0.3628 0.043 Uiso 1 1 calc R U . . .
O1 O -0.2156(4) 0.3473(3) 0.48241(16) 0.0685(13) Uani 1 1 d . . . . .
N1 N -0.0887(4) 0.0465(3) 0.38581(18) 0.0369(10) Uani 1 1 d . . . . .
H1A H -0.1393 -0.0020 0.4057 0.044 Uiso 1 1 calc R U . . .
C8 C -0.1886(5) 0.1101(3) 0.3575(2) 0.0404(12) Uani 1 1 d . . . . .
H8A H -0.1413 0.1624 0.3420 0.048 Uiso 1 1 calc R U . . .
H8B H -0.2322 0.0810 0.3228 0.048 Uiso 1 1 calc R U . . .
C7 C -0.4558(5) 0.1770(4) 0.3187(2) 0.0541(15) Uani 1 1 d . . . . .
H7A H -0.5115 0.2245 0.3032 0.081 Uiso 1 1 calc R U . . .
H7B H -0.3915 0.1601 0.2877 0.081 Uiso 1 1 calc R U . . .
H7C H -0.5109 0.1262 0.3289 0.081 Uiso 1 1 calc R U . . .
C6 C -0.4846(6) 0.2399(4) 0.4203(3) 0.0659(17) Uani 1 1 d . . . . .
H6A H -0.4391 0.2602 0.4568 0.099 Uiso 1 1 calc R U . . .
H6B H -0.5353 0.2885 0.4028 0.099 Uiso 1 1 calc R U . . .
H6C H -0.5444 0.1917 0.4307 0.099 Uiso 1 1 calc R U . . .
C1 C -0.1778(5) 0.3781(3) 0.4333(2) 0.0385(12) Uani 1 1 d . . . . .
C3 C 0.0599(5) 0.3369(3) 0.40956(19) 0.0290(10) Uani 1 1 d . . . . .
H3A H 0.0617 0.2951 0.4445 0.035 Uiso 1 1 calc R U . . .
C2 C -0.0358(5) 0.4158(3) 0.4233(2) 0.0352(11) Uani 1 1 d . . . . .
H2A H -0.0054 0.4506 0.4591 0.042 Uiso 1 1 calc R U . . .
C9 C 0.0007(6) 0.0868(4) 0.4328(3) 0.0578(15) Uani 1 1 d . . . . .
H9A H 0.0610 0.0419 0.4483 0.087 Uiso 1 1 calc R U . . .
H9B H 0.0518 0.1345 0.4144 0.087 Uiso 1 1 calc R U . . .
H9C H -0.0526 0.1102 0.4660 0.087 Uiso 1 1 calc R U . . .
C5 C -0.2940(5) 0.1398(3) 0.4028(2) 0.0446(13) Uani 1 1 d . . . . .
H5A H -0.3468 0.0885 0.4158 0.054 Uiso 1 1 calc R U . . .
H5B H -0.2507 0.1650 0.4390 0.054 Uiso 1 1 calc R U . . .
C10 C -0.0068(6) 0.0061(4) 0.3344(3) 0.0520(14) Uani 1 1 d . . . . .
H10A H -0.0660 -0.0198 0.3043 0.078 Uiso 1 1 calc R U . . .
H10B H 0.0469 0.0519 0.3153 0.078 Uiso 1 1 calc R U . . .
H10C H 0.0510 -0.0396 0.3509 0.078 Uiso 1 1 calc R U . . .


_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 O6 1.595(3) . ?
V1 O11 1.784(3) . ?
V1 O7 1.8168(18) . ?
V1 O9 1.944(3) . ?
V1 O2 2.071(3) . ?
V2 O8 1.588(3) . ?
V2 O10 1.8300(8) . ?
V2 O5 1.861(3) 3 ?
V2 O11 1.874(3) . ?
V2 O3 2.047(3) 3 ?
O10 V2 1.8300(8) 3 ?
O3 C1 1.297(5) . ?
O3 V2 2.047(3) 3 ?
O9 C3 1.402(5) . ?
O4 C4 1.248(5) . ?
O5 C2 1.406(5) . ?
O5 V2 1.861(3) 3 ?
O7 V1 1.8168(18) 3 ?
O2 C4 1.271(5) . ?
C4 C3 1.504(6) . ?
N2 C7 1.480(6) . ?
N2 C5 1.483(6) . ?
N2 C6 1.487(6) . ?
N2 H2B 0.9800 . ?
O1 C1 1.218(5) . ?
N1 C9 1.477(6) . ?
N1 C8 1.504(6) . ?
N1 C10 1.505(6) . ?
N1 H1A 0.9800 . ?
C8 C5 1.500(7) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C6 H6A 0.9600 . ?
C6 H6B 0.9600 . ?
C6 H6C 0.9600 . ?
C1 C2 1.534(7) . ?
C3 C2 1.542(6) . ?
C3 H3A 0.9800 . ?
C2 H2A 0.9800 . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 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
O6 V1 O11 106.01(16) . . ?
O6 V1 O7 101.25(16) . . ?
O11 V1 O7 98.91(11) . . ?
O6 V1 O9 106.25(15) . . ?
O11 V1 O9 144.92(14) . . ?
O7 V1 O9 88.02(9) . . ?
O6 V1 O2 93.68(15) . . ?
O11 V1 O2 87.04(12) . . ?
O7 V1 O2 161.64(12) . . ?
O9 V1 O2 77.48(12) . . ?
O8 V2 O10 101.23(15) . . ?
O8 V2 O5 101.05(16) . 3 ?
O10 V2 O5 100.58(11) . 3 ?
O8 V2 O11 103.25(16) . . ?
O10 V2 O11 90.32(13) . . ?
O5 V2 O11 150.81(13) 3 . ?
O8 V2 O3 104.22(15) . 3 ?
O10 V2 O3 154.28(14) . 3 ?
O5 V2 O3 78.21(13) 3 3 ?
O11 V2 O3 80.35(13) . 3 ?
V1 O11 V2 110.92(15) . . ?
V2 O10 V2 166.1(2) . 3 ?
C1 O3 V2 113.3(3) . 3 ?
C3 O9 V1 118.6(3) . . ?
C2 O5 V2 111.7(3) . 3 ?
V1 O7 V1 126.0(2) . 3 ?
C4 O2 V1 116.7(3) . . ?
O4 C4 O2 124.8(4) . . ?
O4 C4 C3 120.4(4) . . ?
O2 C4 C3 114.8(4) . . ?
C7 N2 C5 114.4(4) . . ?
C7 N2 C6 108.6(4) . . ?
C5 N2 C6 110.5(4) . . ?
C7 N2 H2B 107.7 . . ?
C5 N2 H2B 107.7 . . ?
C6 N2 H2B 107.7 . . ?
C9 N1 C8 114.9(4) . . ?
C9 N1 C10 110.3(4) . . ?
C8 N1 C10 108.0(4) . . ?
C9 N1 H1A 107.8 . . ?
C8 N1 H1A 107.8 . . ?
C10 N1 H1A 107.8 . . ?
C5 C8 N1 112.4(4) . . ?
C5 C8 H8A 109.1 . . ?
N1 C8 H8A 109.1 . . ?
C5 C8 H8B 109.1 . . ?
N1 C8 H8B 109.1 . . ?
H8A C8 H8B 107.9 . . ?
N2 C7 H7A 109.5 . . ?
N2 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
N2 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
N2 C6 H6A 109.5 . . ?
N2 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
N2 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
O1 C1 O3 125.2(5) . . ?
O1 C1 C2 123.0(5) . . ?
O3 C1 C2 111.5(4) . . ?
O9 C3 C4 109.7(3) . . ?
O9 C3 C2 107.3(4) . . ?
C4 C3 C2 108.9(4) . . ?
O9 C3 H3A 110.3 . . ?
C4 C3 H3A 110.3 . . ?
C2 C3 H3A 110.3 . . ?
O5 C2 C1 106.5(4) . . ?
O5 C2 C3 107.4(3) . . ?
C1 C2 C3 108.3(4) . . ?
O5 C2 H2A 111.5 . . ?
C1 C2 H2A 111.5 . . ?
C3 C2 H2A 111.5 . . ?
N1 C9 H9A 109.5 . . ?
N1 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
N1 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
N2 C5 C8 110.7(4) . . ?
N2 C5 H5A 109.5 . . ?
C8 C5 H5A 109.5 . . ?
N2 C5 H5B 109.5 . . ?
C8 C5 H5B 109.5 . . ?
H5A C5 H5B 108.1 . . ?
N1 C10 H10A 109.5 . . ?
N1 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
N1 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?

_refine_diff_density_max         0.266
_refine_diff_density_min         -0.257
_refine_diff_density_rms         0.058

