# 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 2019

####################################################################### 
# 
# 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 1893278'
loop_
_audit_author_name
_audit_author_address
'Syamal Chakrabarti'
;University of Calcutta
India
;
_audit_update_record             
;
2019-01-24 deposited with the CCDC.	2019-08-05 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C9 H10 N O7 V'
_chemical_formula_weight         295.12

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           43
_space_group_name_H-M_alt        'F d d 2'
_space_group_name_Hall           'F 2 -2d'

_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'
'x+1/4, -y+1/4, z+1/4'
'-x+1/4, y+1/4, z+1/4'
'x, y+1/2, z+1/2'
'-x, -y+1/2, z+1/2'
'x+1/4, -y+3/4, z+3/4'
'-x+1/4, y+3/4, z+3/4'
'x+1/2, y, z+1/2'
'-x+1/2, -y, z+1/2'
'x+3/4, -y+1/4, z+3/4'
'-x+3/4, y+1/4, z+3/4'
'x+1/2, y+1/2, z'
'-x+1/2, -y+1/2, z'
'x+3/4, -y+3/4, z+1/4'
'-x+3/4, y+3/4, z+1/4'

_cell_length_a                   29.035(3)
_cell_length_b                   20.1894(9)
_cell_length_c                   7.8421(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     4597.0(6)
_cell_formula_units_Z            16
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    3772
_cell_measurement_theta_min      3.46
_cell_measurement_theta_max      27.50

_exptl_crystal_description       needle
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.07

_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.706
_exptl_crystal_F_000             2400
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_absorpt_coefficient_mu    0.890
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   'ABSPACK, Oxford Diffraction Ltd'
_exptl_absorpt_correction_T_min  0.928
_exptl_absorpt_correction_T_max  0.940
_exptl_absorpt_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            3772
_diffrn_reflns_av_unetI/netI     0.0331
_diffrn_reflns_av_R_equivalents  0.0239
_diffrn_reflns_limit_h_min       -30
_diffrn_reflns_limit_h_max       37
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -6
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         3.457
_diffrn_reflns_theta_max         27.496
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.967
_diffrn_measured_fraction_theta_full 0.980
_diffrn_reflns_Laue_measured_fraction_max 0.967
_diffrn_reflns_Laue_measured_fraction_full 0.980
_diffrn_reflns_point_group_measured_fraction_max 0.659
_diffrn_reflns_point_group_measured_fraction_full 0.677
_reflns_number_total             2632
_reflns_number_gt                1646
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.270
_reflns_Friedel_fraction_max     0.302
_reflns_Friedel_fraction_full    0.322

_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       '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-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    PLATON(Spek,2004)
_computing_publication_material  'SHELXL-2016/6, PLATON, WINGX (Ferrugia, 2012)'


_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)+(0.0327P)²+1.7721P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Classical Flack method preferred over Parsons because s.u. lower.
;
_refine_ls_abs_structure_Flack   0.00(3)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         1736
_refine_ls_number_parameters     170
_refine_ls_number_restraints     4
_refine_ls_R_factor_all          0.0283
_refine_ls_R_factor_gt           0.0260
_refine_ls_wR_factor_ref         0.0655
_refine_ls_wR_factor_gt          0.0641
_refine_ls_goodness_of_fit_ref   1.071
_refine_ls_restrained_S_all      1.070
_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 0.19364(2) 0.11379(2) 0.71208(7) 0.01550(14) Uani 1 1 d . . . . .
C1 C 0.23100(11) 0.15190(13) 1.0497(4) 0.0137(6) Uani 1 1 d . . . . .
C2 C 0.26076(11) 0.15335(14) 1.1881(4) 0.0187(7) Uani 1 1 d . . . . .
H2 H 0.254661 0.179512 1.283046 0.022 Uiso 1 1 calc R U . . .
C3 C 0.30033(11) 0.11389(14) 1.1792(4) 0.0196(8) Uani 1 1 d . . . . .
H3 H 0.321296 0.114266 1.268841 0.023 Uiso 1 1 calc R U . . .
C4 C 0.30858(11) 0.07424(14) 1.0381(4) 0.0165(6) Uani 1 1 d . . . . .
H4 H 0.334552 0.047374 1.032533 0.020 Uiso 1 1 calc R U . . .
C5 C 0.27723(10) 0.07578(13) 0.9065(4) 0.0138(6) Uani 1 1 d . . . . .
C6 C 0.27705(10) 0.03676(13) 0.7424(4) 0.0153(6) Uani 1 1 d . . . . .
C7 C 0.18544(11) 0.18714(13) 1.0284(4) 0.0158(6) Uani 1 1 d . . . . .
C8 C 0.12969(11) 0.10910(14) 0.4294(4) 0.0204(7) Uani 1 1 d . . . . .
H8A H 0.154348 0.106695 0.346225 0.025 Uiso 1 1 calc R U . . .
H8B H 0.119614 0.154796 0.437626 0.025 Uiso 1 1 calc R U . . .
C9 C 0.08974(13) 0.06534(16) 0.3739(5) 0.0276(8) Uani 1 1 d . . . . .
H9A H 0.100273 0.020532 0.361491 0.041 Uiso 1 1 calc R U . . .
H9B H 0.077894 0.080892 0.266889 0.041 Uiso 1 1 calc R U . . .
H9C H 0.065841 0.067000 0.458439 0.041 Uiso 1 1 calc R U . . .
N1 N 0.24013(9) 0.11485(11) 0.9148(3) 0.0134(5) Uani 1 1 d . . . . .
O1 O 0.24173(7) 0.04970(10) 0.6463(3) 0.0179(5) Uani 1 1 d . . . . .
O2 O 0.30778(8) -0.00256(9) 0.7075(4) 0.0203(4) Uani 1 1 d . . . . .
O5 O 0.14583(8) 0.08661(10) 0.5920(3) 0.0183(5) Uani 1 1 d . . . . .
O3 O 0.16534(7) 0.17251(10) 0.8832(3) 0.0186(5) Uani 1 1 d . . . . .
O4 O 0.16960(8) 0.22402(11) 1.1362(3) 0.0218(5) Uani 1 1 d . . . . .
O6 O 0.21320(8) 0.17144(10) 0.5950(3) 0.0210(5) Uani 1 1 d . . . . .
O7 O 0.16742(8) 0.03148(11) 0.8784(3) 0.0207(5) Uani 1 1 d D . . . .
H71 H 0.1411(8) 0.0152(16) 0.866(5) 0.025 Uiso 1 1 d D U . . .
H72 H 0.1789(11) 0.0207(17) 0.974(3) 0.025 Uiso 1 1 d D 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 1.588(2) . ?
V1 O5 1.765(2) . ?
V1 O3 1.970(2) . ?
V1 O1 1.972(2) . ?
V1 N1 2.086(3) . ?
V1 O7 2.245(2) . ?
C1 N1 1.322(4) . ?
C1 C2 1.388(4) . ?
C1 C7 1.511(4) . ?
C2 C3 1.400(4) . ?
C2 H2 0.9300 . ?
C3 C4 1.387(4) . ?
C3 H3 0.9300 . ?
C4 C5 1.376(4) . ?
C4 H4 0.9300 . ?
C5 N1 1.337(4) . ?
C5 C6 1.509(4) . ?
C6 O2 1.225(4) . ?
C6 O1 1.299(4) . ?
C7 O4 1.217(4) . ?
C7 O3 1.314(4) . ?
C8 O5 1.432(4) . ?
C8 C9 1.522(4) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
O7 H71 0.838(19) . ?
O7 H72 0.85(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
O6 V1 O5 101.57(12) . . ?
O6 V1 O3 95.86(11) . . ?
O5 V1 O3 102.86(10) . . ?
O6 V1 O1 94.38(11) . . ?
O5 V1 O1 102.31(10) . . ?
O3 V1 O1 150.26(10) . . ?
O6 V1 N1 101.65(11) . . ?
O5 V1 N1 156.78(10) . . ?
O3 V1 N1 75.20(10) . . ?
O1 V1 N1 75.40(10) . . ?
O6 V1 O7 178.85(10) . . ?
O5 V1 O7 79.23(9) . . ?
O3 V1 O7 84.74(9) . . ?
O1 V1 O7 84.63(9) . . ?
N1 V1 O7 77.55(9) . . ?
N1 C1 C2 120.8(3) . . ?
N1 C1 C7 110.7(3) . . ?
C2 C1 C7 128.4(3) . . ?
C1 C2 C3 117.4(3) . . ?
C1 C2 H2 121.3 . . ?
C3 C2 H2 121.3 . . ?
C4 C3 C2 120.7(3) . . ?
C4 C3 H3 119.7 . . ?
C2 C3 H3 119.7 . . ?
C5 C4 C3 118.1(3) . . ?
C5 C4 H4 120.9 . . ?
C3 C4 H4 120.9 . . ?
N1 C5 C4 120.6(3) . . ?
N1 C5 C6 110.3(3) . . ?
C4 C5 C6 129.0(3) . . ?
O2 C6 O1 125.1(3) . . ?
O2 C6 C5 121.7(3) . . ?
O1 C6 C5 113.1(2) . . ?
O4 C7 O3 124.9(3) . . ?
O4 C7 C1 122.8(3) . . ?
O3 C7 C1 112.3(3) . . ?
O5 C8 C9 108.7(3) . . ?
O5 C8 H8A 110.0 . . ?
C9 C8 H8A 110.0 . . ?
O5 C8 H8B 110.0 . . ?
C9 C8 H8B 110.0 . . ?
H8A C8 H8B 108.3 . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C8 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C1 N1 C5 122.3(3) . . ?
C1 N1 V1 119.1(2) . . ?
C5 N1 V1 118.6(2) . . ?
C6 O1 V1 122.6(2) . . ?
C8 O5 V1 129.33(19) . . ?
C7 O3 V1 122.73(19) . . ?
V1 O7 H71 122(2) . . ?
V1 O7 H72 125(2) . . ?
H71 O7 H72 111(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
O7 H71 O4 0.838(19) 1.95(2) 2.781(3) 169(4) 8_544
O7 H72 O2 0.85(2) 1.90(2) 2.743(4) 168(4) 10

_refine_diff_density_max         0.248
_refine_diff_density_min         -0.240
_refine_diff_density_rms         0.054

####################################################################### 
# 
# 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_shelx_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 1893279'
loop_
_audit_author_name
_audit_author_address
'Syamal Chakrabarti'
;University of Calcutta
India
;
_audit_update_record             
;
2019-01-24 deposited with the CCDC.	2019-08-05 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C10 H12 N O7 V'
_chemical_formula_weight         309.15

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           43
_space_group_name_H-M_alt        'F d d 2'
_space_group_name_Hall           'F 2 -2d'

_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'
'-x+1/4, y+1/4, z+1/4'
'x+1/4, -y+1/4, z+1/4'
'x, y+1/2, z+1/2'
'-x, -y+1/2, z+1/2'
'-x+1/4, y+3/4, z+3/4'
'x+1/4, -y+3/4, z+3/4'
'x+1/2, y, z+1/2'
'-x+1/2, -y, z+1/2'
'-x+3/4, y+1/4, z+3/4'
'x+3/4, -y+1/4, z+3/4'
'x+1/2, y+1/2, z'
'-x+1/2, -y+1/2, z'
'-x+3/4, y+3/4, z+1/4'
'x+3/4, -y+3/4, z+1/4'

_cell_length_a                   22.236(8)
_cell_length_b                   30.525(10)
_cell_length_c                   7.549(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     5124(3)
_cell_formula_units_Z            16
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    1829
_cell_measurement_theta_min      2.27
_cell_measurement_theta_max      19.18

_exptl_crystal_description       neddle
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.603
_exptl_crystal_F_000             2528
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.08
_exptl_absorpt_coefficient_mu    0.802
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed tube'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            8954
_diffrn_reflns_av_unetI/netI     0.0628
_diffrn_reflns_av_R_equivalents  0.0643
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_k_min       -34
_diffrn_reflns_limit_k_max       37
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_theta_min         2.266
_diffrn_reflns_theta_max         25.990
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.909
_diffrn_reflns_point_group_measured_fraction_full 0.934
_reflns_number_total             2290
_reflns_number_gt                1863
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.708
_reflns_Friedel_fraction_max     0.819
_reflns_Friedel_fraction_full    0.860

_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 APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker 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)+(0.0289P)²+2.7287P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 644 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.04(3)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         2520
_refine_ls_number_parameters     181
_refine_ls_number_restraints     4
_refine_ls_R_factor_all          0.0559
_refine_ls_R_factor_gt           0.0417
_refine_ls_wR_factor_ref         0.0896
_refine_ls_wR_factor_gt          0.0837
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_restrained_S_all      1.028
_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 0.90207(4) 0.18605(3) 0.37410(14) 0.0468(3) Uani 1 1 d . . . . .
O7 O 0.9758(2) 0.16463(14) 0.1956(7) 0.0724(14) Uani 1 1 d D . . . .
O1 O 0.95694(15) 0.23431(12) 0.4338(5) 0.0555(10) Uani 1 1 d . . . . .
O2 O 0.99100(17) 0.30196(12) 0.3754(7) 0.0713(12) Uani 1 1 d . . . . .
O6 O 0.85040(15) 0.20258(12) 0.5008(5) 0.0560(10) Uani 1 1 d . . . . .
O3 O 0.84826(17) 0.15720(12) 0.2028(6) 0.0595(11) Uani 1 1 d . . . . .
O5 O 0.93120(19) 0.14282(12) 0.5009(6) 0.0615(11) Uani 1 1 d . . . . .
O4 O 0.7922(2) 0.16137(14) -0.0419(6) 0.0812(14) Uani 1 1 d . . . . .
N1 N 0.89270(16) 0.23048(12) 0.1661(6) 0.0391(10) Uani 1 1 d . . . . .
C5 C 0.9230(2) 0.26795(14) 0.1738(7) 0.0378(12) Uani 1 1 d . . . . .
C1 C 0.8559(2) 0.22154(17) 0.0354(7) 0.0422(12) Uani 1 1 d . . . . .
C7 C 0.8283(3) 0.17635(19) 0.0596(9) 0.0556(15) Uani 1 1 d . . . . .
C10 C 0.9550(3) 0.0556(2) 0.6684(15) 0.104(3) Uani 1 1 d . . . . .
H10A H 0.914557 0.045200 0.682303 0.157 Uiso 1 1 calc R U . . .
H10B H 0.982283 0.035566 0.724859 0.157 Uiso 1 1 calc R U . . .
H10C H 0.964530 0.057520 0.544545 0.157 Uiso 1 1 calc R U . . .
C3 C 0.8779(2) 0.29043(18) -0.0939(8) 0.0630(17) Uani 1 1 d . . . . .
H3 H 0.872813 0.310913 -0.183855 0.076 Uiso 1 1 calc R U . . .
C4 C 0.9162(2) 0.29869(16) 0.0437(8) 0.0505(14) Uani 1 1 d . . . . .
H4 H 0.937447 0.324921 0.048768 0.061 Uiso 1 1 calc R U . . .
C2 C 0.8463(2) 0.25051(19) -0.0975(8) 0.0624(16) Uani 1 1 d . . . . .
H2 H 0.819615 0.244175 -0.188787 0.075 Uiso 1 1 calc R U . . .
C8 C 0.9162(3) 0.1305(2) 0.6764(9) 0.0732(19) Uani 1 1 d . . . . .
H8A H 0.876260 0.117767 0.677894 0.088 Uiso 1 1 calc R U . . .
H8B H 0.915789 0.156314 0.751364 0.088 Uiso 1 1 calc R U . . .
C9 C 0.9606(3) 0.0980(2) 0.7480(11) 0.084(2) Uani 1 1 d . . . . .
H9A H 1.001037 0.108910 0.727974 0.101 Uiso 1 1 calc R U . . .
H9B H 0.954893 0.095266 0.874921 0.101 Uiso 1 1 calc R U . . .
C6 C 0.9608(2) 0.26975(17) 0.3406(8) 0.0481(14) Uani 1 1 d . . . . .
H71 H 0.9969(17) 0.1435(10) 0.219(6) 0.035(14) Uiso 1 1 d D . . . .
H72 H 0.988(2) 0.1767(16) 0.101(5) 0.07(2) Uiso 1 1 d D . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
V1 O6 1.578(4) . ?
V1 O5 1.754(4) . ?
V1 O1 1.965(3) . ?
V1 O3 1.970(4) . ?
V1 N1 2.085(4) . ?
V1 O7 2.220(4) . ?
O7 H71 0.82(2) . ?
O7 H72 0.84(2) . ?
O1 C6 1.293(6) . ?
O2 C6 1.219(5) . ?
O3 C7 1.307(7) . ?
O5 C8 1.417(7) . ?
O4 C7 1.200(7) . ?
N1 C1 1.310(6) . ?
N1 C5 1.329(5) . ?
C5 C4 1.366(6) . ?
C5 C6 1.515(7) . ?
C1 C2 1.354(7) . ?
C1 C7 1.521(7) . ?
C10 C9 1.433(9) . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C3 C4 1.367(8) . ?
C3 C2 1.407(7) . ?
C3 H3 0.9300 . ?
C4 H4 0.9300 . ?
C2 H2 0.9300 . ?
C8 C9 1.502(8) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 H9A 0.9700 . ?
C9 H9B 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
O6 V1 O5 100.3(2) . . ?
O6 V1 O1 94.21(19) . . ?
O5 V1 O1 102.10(18) . . ?
O6 V1 O3 95.66(17) . . ?
O5 V1 O3 104.25(19) . . ?
O1 V1 O3 149.64(16) . . ?
O6 V1 N1 100.11(18) . . ?
O5 V1 N1 159.55(17) . . ?
O1 V1 N1 75.35(15) . . ?
O3 V1 N1 74.68(17) . . ?
O6 V1 O7 178.43(19) . . ?
O5 V1 O7 80.62(18) . . ?
O1 V1 O7 84.35(17) . . ?
O3 V1 O7 85.31(18) . . ?
N1 V1 O7 78.95(16) . . ?
V1 O7 H71 122(3) . . ?
V1 O7 H72 128(3) . . ?
H71 O7 H72 110(4) . . ?
C6 O1 V1 123.0(3) . . ?
C7 O3 V1 123.3(4) . . ?
C8 O5 V1 128.5(4) . . ?
C1 N1 C5 121.9(4) . . ?
C1 N1 V1 119.6(3) . . ?
C5 N1 V1 118.4(3) . . ?
N1 C5 C4 120.2(5) . . ?
N1 C5 C6 110.4(4) . . ?
C4 C5 C6 129.3(4) . . ?
N1 C1 C2 121.3(5) . . ?
N1 C1 C7 110.5(5) . . ?
C2 C1 C7 128.1(5) . . ?
O4 C7 O3 125.8(5) . . ?
O4 C7 C1 122.6(6) . . ?
O3 C7 C1 111.6(5) . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C4 C3 C2 119.1(5) . . ?
C4 C3 H3 120.5 . . ?
C2 C3 H3 120.5 . . ?
C5 C4 C3 119.2(5) . . ?
C5 C4 H4 120.4 . . ?
C3 C4 H4 120.4 . . ?
C1 C2 C3 118.2(5) . . ?
C1 C2 H2 120.9 . . ?
C3 C2 H2 120.9 . . ?
O5 C8 C9 110.9(5) . . ?
O5 C8 H8A 109.5 . . ?
C9 C8 H8A 109.5 . . ?
O5 C8 H8B 109.5 . . ?
C9 C8 H8B 109.5 . . ?
H8A C8 H8B 108.0 . . ?
C10 C9 C8 112.9(6) . . ?
C10 C9 H9A 109.0 . . ?
C8 C9 H9A 109.0 . . ?
C10 C9 H9B 109.0 . . ?
C8 C9 H9B 109.0 . . ?
H9A C9 H9B 107.8 . . ?
O2 C6 O1 126.5(5) . . ?
O2 C6 C5 120.9(5) . . ?
O1 C6 C5 112.6(4) . . ?

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
O7 H71 O4 0.82(2) 1.96(3) 2.752(5) 164(4) 4
O7 H72 O2 0.84(2) 1.89(3) 2.725(6) 172(6) 6_754

_refine_diff_density_max         0.204
_refine_diff_density_min         -0.234
_refine_diff_density_rms         0.046

