# 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_Compound1
_database_code_depnum_ccdc_archive 'CCDC 1431965'
_audit_update_record             
;
2015-10-17 deposited with the CCDC.
2016-04-06 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C16 H20 N4 O10 V'
_chemical_formula_weight         479.30

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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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'

_cell_length_a                   6.7527(2)
_cell_length_b                   12.1817(4)
_cell_length_c                   13.4598(5)
_cell_angle_alpha                70.6580(10)
_cell_angle_beta                 76.2030(10)
_cell_angle_gamma                86.5320(10)
_cell_volume                     1014.35(6)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    11379
_cell_measurement_theta_min      2.79
_cell_measurement_theta_max      28.71

_exptl_crystal_description       Prismatic
_exptl_crystal_colour            Blue
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.569
_exptl_crystal_F_000             494
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.14
_exptl_absorpt_coefficient_mu    0.552
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   Empirical
_exptl_absorpt_correction_T_min  0.6902
_exptl_absorpt_correction_T_max  0.7458
_exptl_absorpt_process_details   'Bruker SADABS (Bruker, 1999)'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       'Phi and Omega Scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            20246
_diffrn_reflns_av_unetI/netI     0.0232
_diffrn_reflns_av_R_equivalents  0.0259
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.788
_diffrn_reflns_theta_max         28.736
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             5240
_reflns_number_gt                4622
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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       'Bruker ApexII'
_computing_cell_refinement       'Bruker Apex II'
_computing_data_reduction        'Bruker Apex II'
_computing_structure_solution    'SHELXL-2014 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    'SHELXL-2014 (Sheldrick, 2014)'
_computing_publication_material  'SHELXL-2014 (Sheldrick, 2014)'

_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)+(0.0297P)²+0.6719P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5240
_refine_ls_number_parameters     280
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0348
_refine_ls_R_factor_gt           0.0283
_refine_ls_wR_factor_ref         0.0715
_refine_ls_wR_factor_gt          0.0685
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_restrained_S_all      1.052
_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_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 0.16822(3) 0.24384(2) 0.37168(2) 0.00698(6) Uani 1 1 d . . . . .
C1A C -0.20418(19) 0.12587(11) 0.50407(10) 0.0086(2) Uani 1 1 d . . . . .
C1B C -0.03820(18) 0.40800(11) 0.20357(10) 0.0086(2) Uani 1 1 d . . . . .
C2A C -0.14929(19) 0.08110(11) 0.41041(10) 0.0086(2) Uani 1 1 d . . . . .
C2B C 0.16529(19) 0.37836(11) 0.14689(10) 0.0086(2) Uani 1 1 d . . . . .
C3A C 0.04641(19) 0.05556(11) 0.26670(10) 0.0096(2) Uani 1 1 d . . . . .
C3B C 0.46687(18) 0.30488(11) 0.13060(10) 0.0089(2) Uani 1 1 d . . . . .
C4A C 0.2049(2) 0.05148(12) 0.17922(11) 0.0139(3) Uani 1 1 d . . . . .
H4A H 0.3285 0.0907 0.1631 0.017 Uiso 1 1 calc R U . . .
C4B C 0.64786(19) 0.24718(11) 0.14565(11) 0.0119(2) Uani 1 1 d . . . . .
H4B H 0.6706 0.2108 0.2144 0.014 Uiso 1 1 calc R U . . .
C5A C 0.1693(2) -0.01350(12) 0.11793(11) 0.0166(3) Uani 1 1 d . . . . .
H5A H 0.2713 -0.0178 0.0592 0.020 Uiso 1 1 calc R U . . .
C5B C 0.7921(2) 0.24653(12) 0.05337(11) 0.0140(3) Uani 1 1 d . . . . .
H5B H 0.9139 0.2084 0.0606 0.017 Uiso 1 1 calc R U . . .
C6A C -0.0176(2) -0.07330(12) 0.14218(11) 0.0165(3) Uani 1 1 d . . . . .
H6A H -0.0364 -0.1149 0.0982 0.020 Uiso 1 1 calc R U . . .
C6B C 0.7593(2) 0.30208(12) -0.05126(11) 0.0147(3) Uani 1 1 d . . . . .
H6B H 0.8605 0.3000 -0.1111 0.018 Uiso 1 1 calc R U . . .
C7A C -0.1737(2) -0.07194(12) 0.22948(11) 0.0139(3) Uani 1 1 d . . . . .
H7A H -0.2965 -0.1120 0.2458 0.017 Uiso 1 1 calc R U . . .
C7B C 0.5809(2) 0.35955(12) -0.06726(10) 0.0137(3) Uani 1 1 d . . . . .
H7B H 0.5592 0.3962 -0.1362 0.016 Uiso 1 1 calc R U . . .
C8A C -0.13711(19) -0.00717(11) 0.29164(10) 0.0098(2) Uani 1 1 d . . . . .
C8B C 0.43475(19) 0.35953(11) 0.02601(10) 0.0098(2) Uani 1 1 d . . . . .
N1A N 0.03310(16) 0.11153(9) 0.34266(8) 0.0087(2) Uani 1 1 d . . . . .
N1B N 0.29276(16) 0.31783(9) 0.20528(8) 0.0083(2) Uani 1 1 d . . . . .
N2A N -0.25671(16) 0.01137(9) 0.38310(8) 0.0090(2) Uani 1 1 d . . . . .
H2A H -0.3775 -0.0166 0.4163 0.011 Uiso 1 1 calc R U . . .
N2B N 0.24201(16) 0.40555(10) 0.03982(8) 0.0103(2) Uani 1 1 d . . . . .
H2B H 0.1825 0.4443 -0.0106 0.012 Uiso 1 1 calc R U . . .
O1 O 0.37022(14) 0.18173(8) 0.40205(7) 0.01181(18) Uani 1 1 d . . . . .
O1A O -0.06329(13) 0.19198(8) 0.50483(7) 0.00975(17) Uani 1 1 d . . . . .
O1B O -0.07520(13) 0.35748(8) 0.30542(7) 0.00995(18) Uani 1 1 d . . . . .
O1W O 0.20725(14) 0.38795(8) 0.41361(7) 0.01165(18) Uani 1 1 d . . . . .
H1W1 H 0.1487 0.4547 0.3903 0.014 Uiso 1 1 d R U . . .
H2W1 H 0.3302 0.4004 0.4198 0.014 Uiso 1 1 d R U . . .
O2A O -0.36754(14) 0.09947(8) 0.57199(7) 0.01094(18) Uani 1 1 d . . . . .
O2B O -0.14974(14) 0.47674(8) 0.15183(7) 0.01153(18) Uani 1 1 d . . . . .
O2W O 0.56787(14) 0.42106(9) 0.43230(8) 0.0162(2) Uani 1 1 d . . . . .
H1W2 H 0.6692 0.3956 0.3926 0.019 Uiso 1 1 d R U . . .
H2W2 H 0.5800 0.3875 0.4989 0.019 Uiso 1 1 d R U . . .
O3W O 0.03223(15) 0.60278(9) 0.36727(8) 0.0170(2) Uani 1 1 d . . . . .
H1W3 H -0.0513 0.6232 0.3228 0.020 Uiso 1 1 d R U . . .
H2W3 H -0.0318 0.6179 0.4237 0.020 Uiso 1 1 d R U . . .
O4W O -0.40299(15) 0.29255(9) 0.65056(9) 0.0199(2) Uani 1 1 d . . . . .
H1W4 H -0.3819 0.2238 0.6404 0.024 Uiso 1 1 d R U . . .
H2W4 H -0.2876 0.3133 0.6543 0.024 Uiso 1 1 d R U . . .
O5W O -0.22407(15) 0.66321(9) 0.23180(8) 0.0171(2) Uani 1 1 d . . . . .
H1W5 H -0.2383 0.5990 0.2133 0.021 Uiso 1 1 d R U . . .
H2W5 H -0.3431 0.6748 0.2625 0.021 Uiso 1 1 d 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 O1 1.5926(9) . ?
V1 O1A 2.0219(9) . ?
V1 O1W 2.0622(9) . ?
V1 N1A 2.0852(11) . ?
V1 N1B 2.0957(10) . ?
V1 O1B 2.2404(9) . ?
C1A O2A 1.2342(15) . ?
C1A O1A 1.2871(15) . ?
C1A C2A 1.4940(17) . ?
C1B O2B 1.2414(15) . ?
C1B O1B 1.2716(15) . ?
C1B C2B 1.4910(17) . ?
C2A N1A 1.3347(16) . ?
C2A N2A 1.3385(16) . ?
C2B N1B 1.3282(16) . ?
C2B N2B 1.3430(16) . ?
C3A N1A 1.3887(16) . ?
C3A C4A 1.4019(17) . ?
C3A C8A 1.4067(17) . ?
C3B N1B 1.3915(15) . ?
C3B C4B 1.3960(17) . ?
C3B C8B 1.4069(17) . ?
C4A C5A 1.3839(19) . ?
C4B C5B 1.3855(18) . ?
C5A C6A 1.409(2) . ?
C5B C6B 1.4103(19) . ?
C6A C7A 1.3830(19) . ?
C6B C7B 1.3821(19) . ?
C7A C8A 1.3939(18) . ?
C7B C8B 1.3996(17) . ?
C8A N2A 1.3809(15) . ?
C8B N2B 1.3813(16) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 V1 O1A 108.21(4) . . ?
O1 V1 O1W 95.23(4) . . ?
O1A V1 O1W 88.07(4) . . ?
O1 V1 N1A 100.63(5) . . ?
O1A V1 N1A 78.89(4) . . ?
O1W V1 N1A 161.96(4) . . ?
O1 V1 N1B 96.50(4) . . ?
O1A V1 N1B 154.28(4) . . ?
O1W V1 N1B 96.88(4) . . ?
N1A V1 N1B 89.85(4) . . ?
O1 V1 O1B 169.12(4) . . ?
O1A V1 O1B 81.53(3) . . ?
O1W V1 O1B 79.98(4) . . ?
N1A V1 O1B 85.77(4) . . ?
N1B V1 O1B 74.57(4) . . ?
O2A C1A O1A 125.57(11) . . ?
O2A C1A C2A 121.92(11) . . ?
O1A C1A C2A 112.50(10) . . ?
O2B C1B O1B 126.96(11) . . ?
O2B C1B C2B 120.50(11) . . ?
O1B C1B C2B 112.53(11) . . ?
N1A C2A N2A 112.77(11) . . ?
N1A C2A C1A 117.82(11) . . ?
N2A C2A C1A 129.40(11) . . ?
N1B C2B N2B 113.01(11) . . ?
N1B C2B C1B 119.09(11) . . ?
N2B C2B C1B 127.90(11) . . ?
N1A C3A C4A 131.34(12) . . ?
N1A C3A C8A 108.06(11) . . ?
C4A C3A C8A 120.57(11) . . ?
N1B C3B C4B 130.82(12) . . ?
N1B C3B C8B 108.27(11) . . ?
C4B C3B C8B 120.88(11) . . ?
C5A C4A C3A 117.05(12) . . ?
C5B C4B C3B 116.92(12) . . ?
C4A C5A C6A 121.69(12) . . ?
C4B C5B C6B 121.90(12) . . ?
C7A C6A C5A 121.89(12) . . ?
C7B C6B C5B 121.75(12) . . ?
C6A C7A C8A 116.36(12) . . ?
C6B C7B C8B 116.33(12) . . ?
N2A C8A C7A 131.25(12) . . ?
N2A C8A C3A 106.35(11) . . ?
C7A C8A C3A 122.40(11) . . ?
N2B C8B C7B 131.61(12) . . ?
N2B C8B C3B 106.16(10) . . ?
C7B C8B C3B 122.22(12) . . ?
C2A N1A C3A 105.72(10) . . ?
C2A N1A V1 110.68(8) . . ?
C3A N1A V1 142.36(9) . . ?
C2B N1B C3B 105.57(10) . . ?
C2B N1B V1 115.81(8) . . ?
C3B N1B V1 137.24(8) . . ?
C2A N2A C8A 107.08(10) . . ?
C2B N2B C8B 106.98(10) . . ?
C1A O1A V1 117.75(8) . . ?
C1B O1B V1 117.10(8) . . ?

_refine_diff_density_max         0.375
_refine_diff_density_min         -0.462
_refine_diff_density_rms         0.057

_shelxl_version_number           2014-3

####################################################################### 
# 
# 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_Compound2
_database_code_depnum_ccdc_archive 'CCDC 1431966'
_audit_update_record             
;
2015-10-17 deposited with the CCDC.
2016-04-06 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C12 H20 N4 O10 V'
_chemical_formula_weight         431.26

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_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+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   9.1728(7)
_cell_length_b                   23.781(2)
_cell_length_c                   8.3034(7)
_cell_angle_alpha                90
_cell_angle_beta                 93.4410(10)
_cell_angle_gamma                90
_cell_volume                     1808.0(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    4838
_cell_measurement_theta_min      2.22
_cell_measurement_theta_max      28.24

_exptl_crystal_description       Prismatic
_exptl_crystal_colour            Brown
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.584
_exptl_crystal_F_000             892
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.12
_exptl_absorpt_coefficient_mu    0.609
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   Empirical
_exptl_absorpt_correction_T_min  0.6877
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_process_details   'Bruker SADABS (Bruker, 1999)'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71069
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       'Phi and Omega Scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            11545
_diffrn_reflns_av_unetI/netI     0.0316
_diffrn_reflns_av_R_equivalents  0.0242
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_k_max       31
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         1.713
_diffrn_reflns_theta_max         28.459
_diffrn_reflns_theta_full        25.240
_diffrn_measured_fraction_theta_max 0.920
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.920
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.920
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             4197
_reflns_number_gt                3622
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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       'Bruker ApexII'
_computing_cell_refinement       'Bruker Apex II'
_computing_data_reduction        'Bruker Apex II'
_computing_structure_solution    'SHELXL-2014 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    'SHELXL-2014 (Sheldrick, 2014)'
_computing_publication_material  'SHELXL-2014 (Sheldrick, 2014)'

_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)+(0.0518P)²+0.4905P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4197
_refine_ls_number_parameters     244
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0403
_refine_ls_R_factor_gt           0.0342
_refine_ls_wR_factor_ref         0.0932
_refine_ls_wR_factor_gt          0.0893
_refine_ls_goodness_of_fit_ref   1.068
_refine_ls_restrained_S_all      1.068
_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_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 0.61789(3) 0.10729(2) 0.36315(3) 0.01004(9) Uani 1 1 d . . . . .
C1A C 0.83407(17) 0.04775(6) 0.20154(19) 0.0122(3) Uani 1 1 d . . . . .
C1B C 0.66739(18) 0.22600(7) 0.26695(19) 0.0148(3) Uani 1 1 d . . . . .
C2A C 0.71659(17) 0.05559(6) 0.07190(19) 0.0114(3) Uani 1 1 d . . . . .
C2B C 0.51555(18) 0.22623(7) 0.3205(2) 0.0154(3) Uani 1 1 d . . . . .
C3A C 0.72440(18) 0.03540(7) -0.08406(19) 0.0134(3) Uani 1 1 d . . . . .
H3A H 0.8095 0.0184 -0.1153 0.016 Uiso 1 1 calc R U . . .
C3B C 0.4298(2) 0.27400(7) 0.3286(2) 0.0213(4) Uani 1 1 d . . . . .
H3B H 0.4663 0.3087 0.2990 0.026 Uiso 1 1 calc R U . . .
C4A C 0.60525(18) 0.04066(7) -0.19273(19) 0.0133(3) Uani 1 1 d . . . . .
H4A H 0.6090 0.0270 -0.2973 0.016 Uiso 1 1 calc R U . . .
C4B C 0.2903(2) 0.27000(7) 0.3807(2) 0.0251(4) Uani 1 1 d . . . . .
H4B H 0.2324 0.3020 0.3861 0.030 Uiso 1 1 calc R U . . .
C5A C 0.47824(17) 0.06694(6) -0.14351(19) 0.0127(3) Uani 1 1 d . . . . .
C5B C 0.23587(19) 0.21720(8) 0.4258(2) 0.0215(4) Uani 1 1 d . . . . .
C6A C 0.47935(17) 0.08730(7) 0.01574(19) 0.0130(3) Uani 1 1 d . . . . .
H6A H 0.3966 0.1054 0.0494 0.016 Uiso 1 1 calc R U . . .
C6B C 0.32901(18) 0.17030(7) 0.4113(2) 0.0169(3) Uani 1 1 d . . . . .
H6B H 0.2947 0.1349 0.4375 0.020 Uiso 1 1 calc R U . . .
N1A N 0.59467(14) 0.08156(5) 0.12018(15) 0.0112(3) Uani 1 1 d . . . . .
N1B N 0.46450(14) 0.17485(6) 0.36129(16) 0.0130(3) Uani 1 1 d . . . . .
N2A N 0.35706(15) 0.07352(6) -0.24533(17) 0.0175(3) Uani 1 1 d . . . . .
H2A1 H 0.3570 0.0614 -0.3429 0.021 Uiso 1 1 calc R U . . .
H2A2 H 0.2808 0.0898 -0.2119 0.021 Uiso 1 1 calc R U . . .
N2B N 0.10122(17) 0.21087(7) 0.4805(2) 0.0325(4) Uani 1 1 d . . . . .
H2B1 H 0.0453 0.2396 0.4887 0.039 Uiso 1 1 calc R U . . .
H2B2 H 0.0713 0.1781 0.5070 0.039 Uiso 1 1 calc R U . . .
O1 O 0.50106(12) 0.06382(5) 0.42693(13) 0.0138(2) Uani 1 1 d . . . . .
O1A O 0.80093(12) 0.06359(4) 0.34441(13) 0.0127(2) Uani 1 1 d . . . . .
O1B O 0.72663(12) 0.17776(5) 0.25913(14) 0.0151(2) Uani 1 1 d . . . . .
O1W O 0.71435(12) 0.13332(5) 0.57510(13) 0.0147(2) Uani 1 1 d . . . . .
H1W1 H 0.8024 0.1216 0.5894 0.018 Uiso 1 1 d R U . . .
H2W1 H 0.7052 0.1638 0.6165 0.018 Uiso 1 1 d R U . . .
O2A O 0.95270(12) 0.02636(5) 0.17310(14) 0.0162(3) Uani 1 1 d . . . . .
O2B O 0.72882(13) 0.27137(5) 0.23435(15) 0.0215(3) Uani 1 1 d . . . . .
O2W O 1.09690(13) 0.09914(5) -0.05053(15) 0.0198(3) Uani 1 1 d . . . . .
H1W2 H 1.0673 0.0732 -0.0093 0.024 Uiso 1 1 d R U . . .
H2W2 H 1.0430 0.1234 -0.0245 0.024 Uiso 1 1 d R U . . .
O3W O 1.14635(12) 0.03339(5) 0.45047(14) 0.0175(3) Uani 1 1 d . . . . .
H1W3 H 1.0888 0.0303 0.3587 0.021 Uiso 1 1 d R U . . .
H2W3 H 1.1582 0.0018 0.4930 0.021 Uiso 1 1 d R U . . .
O4W O 0.99156(14) 0.10574(5) 0.63183(15) 0.0210(3) Uani 1 1 d . . . . .
H1W4 H 1.0357 0.0806 0.5752 0.025 Uiso 1 1 d R U . . .
H2W4 H 1.0166 0.1025 0.7299 0.025 Uiso 1 1 d R U . . .
O5W O 0.91599(13) 0.31282(5) 0.50196(15) 0.0217(3) Uani 1 1 d . . . . .
H1W5 H 0.8617 0.3037 0.4226 0.026 Uiso 1 1 d R U . . .
H2W5 H 0.8737 0.3153 0.5948 0.026 Uiso 1 1 d 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 O1 1.6019(11) . ?
V1 O1A 1.9887(11) . ?
V1 O1W 2.0190(11) . ?
V1 N1A 2.1068(13) . ?
V1 N1B 2.1350(13) . ?
V1 O1B 2.1571(11) . ?
C1A O2A 1.2367(19) . ?
C1A O1A 1.2980(19) . ?
C1A C2A 1.488(2) . ?
C1B O2B 1.254(2) . ?
C1B O1B 1.2727(19) . ?
C1B C2B 1.487(2) . ?
C2A N1A 1.359(2) . ?
C2A C3A 1.387(2) . ?
C2B N1B 1.359(2) . ?
C2B C3B 1.386(2) . ?
C3A C4A 1.381(2) . ?
C3B C4B 1.378(3) . ?
C4A C5A 1.404(2) . ?
C4B C5B 1.410(3) . ?
C5A N2A 1.365(2) . ?
C5A C6A 1.408(2) . ?
C5B N2B 1.349(2) . ?
C5B C6B 1.415(2) . ?
C6A N1A 1.334(2) . ?
C6B N1B 1.338(2) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 V1 O1A 105.85(5) . . ?
O1 V1 O1W 100.17(5) . . ?
O1A V1 O1W 84.29(5) . . ?
O1 V1 N1A 95.62(5) . . ?
O1A V1 N1A 79.08(5) . . ?
O1W V1 N1A 159.65(5) . . ?
O1 V1 N1B 91.97(5) . . ?
O1A V1 N1B 162.15(5) . . ?
O1W V1 N1B 91.71(5) . . ?
N1A V1 N1B 100.54(5) . . ?
O1 V1 O1B 165.57(5) . . ?
O1A V1 O1B 87.81(4) . . ?
O1W V1 O1B 85.52(5) . . ?
N1A V1 O1B 82.23(5) . . ?
N1B V1 O1B 74.51(5) . . ?
O2A C1A O1A 123.43(14) . . ?
O2A C1A C2A 121.37(14) . . ?
O1A C1A C2A 115.19(13) . . ?
O2B C1B O1B 124.45(16) . . ?
O2B C1B C2B 120.16(15) . . ?
O1B C1B C2B 115.39(14) . . ?
N1A C2A C3A 121.48(14) . . ?
N1A C2A C1A 114.61(13) . . ?
C3A C2A C1A 123.79(14) . . ?
N1B C2B C3B 121.32(15) . . ?
N1B C2B C1B 114.48(14) . . ?
C3B C2B C1B 124.20(15) . . ?
C4A C3A C2A 119.72(15) . . ?
C4B C3B C2B 119.93(16) . . ?
C3A C4A C5A 119.21(15) . . ?
C3B C4B C5B 119.69(16) . . ?
N2A C5A C4A 122.00(15) . . ?
N2A C5A C6A 120.15(14) . . ?
C4A C5A C6A 117.85(14) . . ?
N2B C5B C4B 122.32(16) . . ?
N2B C5B C6B 120.69(16) . . ?
C4B C5B C6B 116.99(16) . . ?
N1A C6A C5A 122.43(14) . . ?
N1B C6B C5B 122.67(15) . . ?
C6A N1A C2A 119.29(14) . . ?
C6A N1A V1 128.57(11) . . ?
C2A N1A V1 112.14(10) . . ?
C6B N1B C2B 119.37(14) . . ?
C6B N1B V1 124.12(11) . . ?
C2B N1B V1 116.21(11) . . ?
C1A O1A V1 117.92(10) . . ?
C1B O1B V1 118.08(10) . . ?

_refine_diff_density_max         0.473
_refine_diff_density_min         -0.346
_refine_diff_density_rms         0.069

_shelxl_version_number           2014-3

