# 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 2020

####################################################################### 
# 
# 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 1876310'
loop_
_audit_author_name
_audit_author_address
'Sanfaori Brahma'
;Department of Chemistry, Gauhati University
India
;
_audit_update_record             
;
2018-10-31 deposited with the CCDC.	2020-01-24 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         C9H9N2O4V
_chemical_formula_sum            'C9 H9 N2 O4 V'
_chemical_formula_weight         260.12

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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

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

_cell_length_a                   7.4612(9)
_cell_length_b                   11.9060(14)
_cell_length_c                   11.1849(13)
_cell_angle_alpha                90
_cell_angle_beta                 99.077(7)
_cell_angle_gamma                90
_cell_volume                     981.1(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    1924
_cell_measurement_theta_min      3.072
_cell_measurement_theta_max      25.998

_exptl_crystal_description       block
_exptl_crystal_colour            brown
_exptl_crystal_density_meas      1.761
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.761
_exptl_crystal_F_000             528
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.19
_exptl_absorpt_coefficient_mu    1.010
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   none
_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            6423
_diffrn_reflns_av_unetI/netI     0.0475
_diffrn_reflns_av_R_equivalents  0.0501
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         3.072
_diffrn_reflns_theta_max         25.998
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             1924
_reflns_number_gt                1709
_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 APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          'Bruker SHELXTL'
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0534P)²+0.6231P] 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_number_reflns         1924
_refine_ls_number_parameters     146
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0406
_refine_ls_R_factor_gt           0.0364
_refine_ls_wR_factor_ref         0.1088
_refine_ls_wR_factor_gt          0.1051
_refine_ls_goodness_of_fit_ref   1.086
_refine_ls_restrained_S_all      1.086
_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 0.22279(5) 0.72945(3) 0.08508(4) 0.02607(18) Uani 1 1 d . . . . .
O1 O 0.1822(3) 0.71424(14) 0.25852(16) 0.0337(4) Uani 1 1 d . . . . .
O2 O 0.3223(3) 0.67701(14) -0.04820(15) 0.0329(4) Uani 1 1 d . . . . .
O3 O 0.3529(3) 0.83771(16) 0.12437(18) 0.0476(6) Uani 1 1 d . . . . .
O4 O 0.0245(3) 0.7720(2) 0.0273(2) 0.0561(6) Uani 1 1 d . . . . .
N1 N 0.2122(3) 0.55106(16) 0.12234(17) 0.0234(4) Uani 1 1 d . . . . .
N2 N 0.1750(3) 0.52920(16) 0.23703(16) 0.0262(4) Uani 1 1 d . . . . .
H1 H 0.1615 0.4622 0.2630 0.031 Uiso 1 1 calc R U . . .
C1 C 0.1618(3) 0.6189(2) 0.3032(2) 0.0261(5) Uani 1 1 d . . . . .
C2 C 0.1263(4) 0.6070(2) 0.4285(2) 0.0352(6) Uani 1 1 d . . . . .
H2 H 0.2283 0.6351 0.4835 0.053 Uiso 1 1 calc R U . . .
H3 H 0.1077 0.5292 0.4455 0.053 Uiso 1 1 calc R U . . .
H4 H 0.0197 0.6491 0.4382 0.053 Uiso 1 1 calc R U . . .
C3 C 0.2348(3) 0.46590(19) 0.0543(2) 0.0261(5) Uani 1 1 d . . . . .
H9 H 0.2220 0.3939 0.0841 0.031 Uiso 1 1 calc R U . . .
C4 C 0.2786(3) 0.4781(2) -0.0646(2) 0.0250(5) Uani 1 1 d . . . . .
C5 C 0.3184(3) 0.58316(19) -0.1121(2) 0.0250(5) Uani 1 1 d . . . . .
C6 C 0.3653(3) 0.5876(2) -0.2283(2) 0.0313(5) Uani 1 1 d . . . . .
H8 H 0.3901 0.6565 -0.2613 0.038 Uiso 1 1 calc R U . . .
C7 C 0.3751(3) 0.4906(2) -0.2941(2) 0.0335(6) Uani 1 1 d . . . . .
H5 H 0.4061 0.4950 -0.3713 0.040 Uiso 1 1 calc R U . . .
C8 C 0.3397(4) 0.3868(2) -0.2473(2) 0.0355(6) Uani 1 1 d . . . . .
H6 H 0.3480 0.3218 -0.2922 0.043 Uiso 1 1 calc R U . . .
C9 C 0.2923(4) 0.3810(2) -0.1340(2) 0.0331(5) Uani 1 1 d . . . . .
H7 H 0.2687 0.3113 -0.1024 0.040 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 O4 1.601(2) . ?
V1 O3 1.6315(19) . ?
V1 O2 1.8742(17) . ?
V1 O1 2.0181(18) . ?
V1 N1 2.1682(19) . ?
O1 C1 1.260(3) . ?
O2 C5 1.324(3) . ?
N1 C3 1.295(3) . ?
N1 N2 1.379(3) . ?
N2 C1 1.312(3) . ?
N2 H1 0.8600 . ?
C1 C2 1.473(3) . ?
C2 H2 0.9600 . ?
C2 H3 0.9600 . ?
C2 H4 0.9600 . ?
C3 C4 1.426(3) . ?
C3 H9 0.9300 . ?
C4 C9 1.405(3) . ?
C4 C5 1.408(3) . ?
C5 C6 1.400(3) . ?
C6 C7 1.377(4) . ?
C6 H8 0.9300 . ?
C7 C8 1.384(4) . ?
C7 H5 0.9300 . ?
C8 C9 1.369(4) . ?
C8 H6 0.9300 . ?
C9 H7 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
O4 V1 O3 109.37(13) . . ?
O4 V1 O2 103.94(11) . . ?
O3 V1 O2 100.60(9) . . ?
O4 V1 O1 98.48(10) . . ?
O3 V1 O1 89.14(8) . . ?
O2 V1 O1 150.81(8) . . ?
O4 V1 N1 109.15(11) . . ?
O3 V1 N1 139.49(10) . . ?
O2 V1 N1 81.81(7) . . ?
O1 V1 N1 73.25(7) . . ?
C1 O1 V1 120.57(15) . . ?
C5 O2 V1 137.09(16) . . ?
C3 N1 N2 117.57(19) . . ?
C3 N1 V1 129.95(16) . . ?
N2 N1 V1 112.48(14) . . ?
C1 N2 N1 114.55(18) . . ?
C1 N2 H1 122.7 . . ?
N1 N2 H1 122.7 . . ?
O1 C1 N2 119.0(2) . . ?
O1 C1 C2 121.0(2) . . ?
N2 C1 C2 120.0(2) . . ?
C1 C2 H2 109.5 . . ?
C1 C2 H3 109.5 . . ?
H2 C2 H3 109.5 . . ?
C1 C2 H4 109.5 . . ?
H2 C2 H4 109.5 . . ?
H3 C2 H4 109.5 . . ?
N1 C3 C4 122.6(2) . . ?
N1 C3 H9 118.7 . . ?
C4 C3 H9 118.7 . . ?
C9 C4 C5 119.0(2) . . ?
C9 C4 C3 118.6(2) . . ?
C5 C4 C3 122.3(2) . . ?
O2 C5 C6 118.8(2) . . ?
O2 C5 C4 122.3(2) . . ?
C6 C5 C4 118.8(2) . . ?
C7 C6 C5 120.5(2) . . ?
C7 C6 H8 119.8 . . ?
C5 C6 H8 119.8 . . ?
C6 C7 C8 121.1(2) . . ?
C6 C7 H5 119.4 . . ?
C8 C7 H5 119.4 . . ?
C9 C8 C7 119.2(2) . . ?
C9 C8 H6 120.4 . . ?
C7 C8 H6 120.4 . . ?
C8 C9 C4 121.4(2) . . ?
C8 C9 H7 119.3 . . ?
C4 C9 H7 119.3 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O4 V1 O2 C5 -84.1(3) . . . . ?
O3 V1 O2 C5 162.7(2) . . . . ?
O1 V1 O2 C5 55.0(3) . . . . ?
N1 V1 O2 C5 23.7(2) . . . . ?
C3 N1 N2 C1 177.1(2) . . . . ?
V1 N1 N2 C1 -3.1(2) . . . . ?
V1 O1 C1 N2 2.9(3) . . . . ?
V1 O1 C1 C2 -178.04(17) . . . . ?
N1 N2 C1 O1 0.4(3) . . . . ?
N1 N2 C1 C2 -178.7(2) . . . . ?
N2 N1 C3 C4 -178.3(2) . . . . ?
V1 N1 C3 C4 1.9(3) . . . . ?
N1 C3 C4 C9 -177.1(2) . . . . ?
N1 C3 C4 C5 6.5(4) . . . . ?
V1 O2 C5 C6 160.37(18) . . . . ?
V1 O2 C5 C4 -23.3(4) . . . . ?
C9 C4 C5 O2 -174.6(2) . . . . ?
C3 C4 C5 O2 1.8(4) . . . . ?
C9 C4 C5 C6 1.7(3) . . . . ?
C3 C4 C5 C6 178.1(2) . . . . ?
O2 C5 C6 C7 175.4(2) . . . . ?
C4 C5 C6 C7 -1.0(4) . . . . ?
C5 C6 C7 C8 -0.2(4) . . . . ?
C6 C7 C8 C9 0.7(4) . . . . ?
C7 C8 C9 C4 0.1(4) . . . . ?
C5 C4 C9 C8 -1.3(4) . . . . ?
C3 C4 C9 C8 -177.9(2) . . . . ?

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
N2 H1 O3 0.86 1.96 2.783(3) 160.1 2_545
C2 H2 O4 0.96 2.45 3.330(4) 152.1 4_676
C2 H3 O3 0.96 2.44 3.269(3) 144.0 2_545
C2 H4 O2 0.96 2.56 3.466(3) 157.4 4_576
C2 H4 O3 0.96 2.59 3.287(3) 129.3 4_576
C6 H8 O1 0.93 2.65 3.360(3) 133.8 4_675
N2 H1 O3 0.86 1.96 2.783(3) 160.1 2_545
C2 H2 O4 0.96 2.45 3.330(4) 152.1 4_676
C2 H3 O3 0.96 2.44 3.269(3) 144.0 2_545
C2 H4 O2 0.96 2.56 3.466(3) 157.4 4_576
C2 H4 O3 0.96 2.59 3.287(3) 129.3 4_576
C6 H8 O1 0.93 2.65 3.360(3) 133.8 4_675

_refine_diff_density_max         0.387
_refine_diff_density_min         -0.507
_refine_diff_density_rms         0.105

####################################################################### 
# 
# 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 1979638'
loop_
_audit_author_name
_audit_author_address
'sanfaori brahma'
;Department of chemistry, Gauhati University
India
;
_audit_update_record             
;
2020-01-23 deposited with the CCDC.	2020-01-24 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         C9H12N3O4V
_chemical_formula_sum            'C9 H12 N3 O4 V'
_chemical_formula_weight         277.16

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           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

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

_cell_length_a                   6.4268(4)
_cell_length_b                   13.3674(10)
_cell_length_c                   13.5577(10)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1164.74(14)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    2274
_cell_measurement_theta_min      3.370
_cell_measurement_theta_max      25.996

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      1.581
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.581
_exptl_crystal_F_000             568
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.16
_exptl_absorpt_coefficient_mu    0.858
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   none
_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                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ scans ω'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            17418
_diffrn_reflns_av_unetI/netI     0.0142
_diffrn_reflns_av_R_equivalents  0.0218
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         3.370
_diffrn_reflns_theta_max         25.996
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             2274
_reflns_number_gt                2238
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.706
_reflns_Friedel_fraction_max     0.999
_reflns_Friedel_fraction_full    0.999

_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    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_publication_material  ?
_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)+(0.0446P)²+0.3212P] 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 927 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.015(5)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         2274
_refine_ls_number_parameters     162
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0246
_refine_ls_R_factor_gt           0.0241
_refine_ls_wR_factor_ref         0.0693
_refine_ls_wR_factor_gt          0.0686
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_restrained_S_all      1.058
_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
C1 C 0.6401(4) 0.46955(18) 0.69662(19) 0.0315(5) Uani 1 1 d . . . . .
C2 C 0.8266(5) 0.4034(2) 0.6984(2) 0.0440(6) Uani 1 1 d . . . . .
H2A H 0.8923 0.4042 0.6348 0.066 Uiso 1 1 calc R U . . .
H2B H 0.9228 0.4272 0.7472 0.066 Uiso 1 1 calc R U . . .
H2C H 0.7850 0.3364 0.7143 0.066 Uiso 1 1 calc R U . . .
C3 C 0.2363(5) 0.5622(2) 0.82733(19) 0.0346(6) Uani 1 1 d . . . . .
C4 C 0.0537(2) 0.62459(13) 0.81967(13) 0.0332(5) Uani 1 1 d G . . . .
C5 C 0.0033(3) 0.67553(13) 0.73355(11) 0.0328(6) Uani 1 1 d G . . . .
C6 C -0.1765(3) 0.73318(13) 0.72934(12) 0.0414(6) Uani 1 1 d G . . . .
H6 H -0.2103 0.7673 0.6717 0.050 Uiso 1 1 calc R U . . .
C7 C -0.3058(2) 0.73990(14) 0.81125(16) 0.0516(8) Uani 1 1 d G . . . .
H7 H -0.4261 0.7785 0.8084 0.062 Uiso 1 1 calc R U . . .
C8 C -0.2554(3) 0.68895(17) 0.89737(14) 0.0590(9) Uani 1 1 d G . . . .
H8 H -0.3419 0.6934 0.9522 0.071 Uiso 1 1 calc R U . . .
C9 C -0.0756(3) 0.63130(16) 0.90158(11) 0.0481(7) Uani 1 1 d G . . . .
H9 H -0.0419 0.5972 0.9592 0.058 Uiso 1 1 calc R U . . .
N1 N 0.3595(3) 0.54312(15) 0.75394(15) 0.0283(4) Uani 1 1 d . . . . .
N2 N 0.5278(3) 0.47953(17) 0.77543(17) 0.0338(5) Uani 1 1 d . . . . .
O1 O 0.5983(3) 0.51593(14) 0.61429(14) 0.0357(4) Uani 1 1 d . . . . .
O2 O 0.1323(3) 0.67792(16) 0.65528(14) 0.0441(5) Uani 1 1 d . . . . .
O3 O 0.1856(4) 0.50406(17) 0.55100(15) 0.0486(5) Uani 1 1 d . . . . .
O4 O 0.4254(4) 0.66381(18) 0.51991(18) 0.0539(6) Uani 1 1 d . . . . .
V V 0.33075(7) 0.58727(3) 0.60379(3) 0.02995(14) Uani 1 1 d . . . . .
N3 N 0.8449(5) 0.6262(2) 0.4600(2) 0.0395(5) Uani 1 1 d . . . . .
H3 H 0.261(5) 0.535(2) 0.888(3) 0.042(8) Uiso 1 1 d . . . . .
H10A H 0.896(6) 0.592(3) 0.405(3) 0.049(9) Uiso 1 1 d . . . . .
H10B H 0.864(8) 0.590(4) 0.498(4) 0.075(16) Uiso 1 1 d . . . . .
H10C H 0.736(9) 0.624(4) 0.469(4) 0.074(17) Uiso 1 1 d . . . . .
H10D H 0.891(7) 0.691(3) 0.471(3) 0.068(13) Uiso 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 N2 1.296(3) . ?
C1 O1 1.305(3) . ?
C1 C2 1.489(4) . ?
C2 H2A 0.9600 . ?
C2 H2B 0.9600 . ?
C2 H2C 0.9600 . ?
C3 N1 1.297(4) . ?
C3 C4 1.444(3) . ?
C3 H3 0.91(4) . ?
C4 C5 1.3900 . ?
C4 C9 1.3900 . ?
C5 O2 1.347(2) . ?
C5 C6 1.3900 . ?
C6 C7 1.3900 . ?
C6 H6 0.9300 . ?
C7 C8 1.3900 . ?
C7 H7 0.9300 . ?
C8 C9 1.3900 . ?
C8 H8 0.9300 . ?
C9 H9 0.9300 . ?
N1 N2 1.406(3) . ?
N1 V 2.128(2) . ?
O1 V 1.9714(19) . ?
O2 V 1.893(2) . ?
O3 V 1.619(2) . ?
O4 V 1.646(2) . ?
N3 H10A 0.94(4) . ?
N3 H10B 0.72(5) . ?
N3 H10C 0.71(6) . ?
N3 H10D 0.93(5) . ?

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
N2 C1 O1 122.8(2) . . ?
N2 C1 C2 119.7(2) . . ?
O1 C1 C2 117.5(2) . . ?
C1 C2 H2A 109.5 . . ?
C1 C2 H2B 109.5 . . ?
H2A C2 H2B 109.5 . . ?
C1 C2 H2C 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
N1 C3 C4 123.7(2) . . ?
N1 C3 H3 120(2) . . ?
C4 C3 H3 116(2) . . ?
C5 C4 C9 120.0 . . ?
C5 C4 C3 122.22(15) . . ?
C9 C4 C3 117.77(15) . . ?
O2 C5 C6 117.78(14) . . ?
O2 C5 C4 122.00(14) . . ?
C6 C5 C4 120.0 . . ?
C5 C6 C7 120.0 . . ?
C5 C6 H6 120.0 . . ?
C7 C6 H6 120.0 . . ?
C6 C7 C8 120.0 . . ?
C6 C7 H7 120.0 . . ?
C8 C7 H7 120.0 . . ?
C9 C8 C7 120.0 . . ?
C9 C8 H8 120.0 . . ?
C7 C8 H8 120.0 . . ?
C8 C9 C4 120.0 . . ?
C8 C9 H9 120.0 . . ?
C4 C9 H9 120.0 . . ?
C3 N1 N2 115.4(2) . . ?
C3 N1 V 128.80(18) . . ?
N2 N1 V 115.64(15) . . ?
C1 N2 N1 108.7(2) . . ?
C1 O1 V 118.13(16) . . ?
C5 O2 V 133.64(15) . . ?
O3 V O4 109.54(13) . . ?
O3 V O2 102.39(11) . . ?
O4 V O2 96.08(10) . . ?
O3 V O1 101.66(11) . . ?
O4 V O1 91.63(10) . . ?
O2 V O1 150.56(9) . . ?
O3 V N1 106.41(10) . . ?
O4 V N1 143.26(12) . . ?
O2 V N1 83.29(8) . . ?
O1 V N1 73.79(8) . . ?
H10A N3 H10B 101(4) . . ?
H10A N3 H10C 117(5) . . ?
H10B N3 H10C 91(6) . . ?
H10A N3 H10D 118(4) . . ?
H10B N3 H10D 117(5) . . ?
H10C N3 H10D 109(5) . . ?

_refine_diff_density_max         0.267
_refine_diff_density_min         -0.247
_refine_diff_density_rms         0.046

####################################################################### 
# 
# 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_CCDC2
_database_code_depnum_ccdc_archive 'CCDC 1938067'
loop_
_audit_author_name
_audit_author_address
'sanfaori brahma'
;Department of chemistry, Gauhati University
India
;
_audit_update_record             
;
2019-07-03 deposited with the CCDC.	2020-01-24 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         C9H9N2O4V
_chemical_formula_sum            'C9 H9 N2 O4 V'
_chemical_formula_weight         260.12

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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

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

_cell_length_a                   7.3510(4)
_cell_length_b                   11.8967(7)
_cell_length_c                   11.1856(6)
_cell_angle_alpha                90
_cell_angle_beta                 99.047(2)
_cell_angle_gamma                90
_cell_volume                     966.04(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    273(2)
_cell_measurement_reflns_used    1896
_cell_measurement_theta_min      3.106
_cell_measurement_theta_max      26.000

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      1.789
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.789
_exptl_crystal_F_000             528
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.20
_exptl_absorpt_coefficient_mu    1.026
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      273(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            11313
_diffrn_reflns_av_unetI/netI     0.0394
_diffrn_reflns_av_R_equivalents  0.0640
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         3.106
_diffrn_reflns_theta_max         26.000
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             1896
_reflns_number_gt                1603
_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 APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.0308P)²+2.4912P] 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_number_reflns         1896
_refine_ls_number_parameters     141
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0568
_refine_ls_R_factor_gt           0.0449
_refine_ls_wR_factor_ref         0.1039
_refine_ls_wR_factor_gt          0.0956
_refine_ls_goodness_of_fit_ref   1.116
_refine_ls_restrained_S_all      1.116
_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
C5 C 0.8191(3) 0.58009(12) 0.38510(15) 0.0119(6) Uani 1 1 d G . . . .
C6 C 0.8662(3) 0.58672(12) 0.26970(16) 0.0138(6) Uani 1 1 d G . . . .
H2 H 0.890214 0.656241 0.237528 0.017 Uiso 1 1 calc R U . . .
C7 C 0.8773(3) 0.48944(16) 0.20240(13) 0.0155(7) Uani 1 1 d G . . . .
H3 H 0.908717 0.493872 0.125195 0.019 Uiso 1 1 calc R U . . .
C8 C 0.8413(3) 0.38552(13) 0.25049(16) 0.0161(7) Uani 1 1 d G . . . .
H4 H 0.848727 0.320435 0.205460 0.019 Uiso 1 1 calc R U . . .
C9 C 0.7943(3) 0.37889(12) 0.36588(16) 0.0146(6) Uani 1 1 d G . . . .
H5 H 0.770234 0.309366 0.398059 0.018 Uiso 1 1 calc R U . . .
C4 C 0.7832(3) 0.47617(15) 0.43319(12) 0.0116(6) Uani 1 1 d G . . . .
C3 C 0.7363(4) 0.4636(3) 0.5532(3) 0.0123(6) Uani 1 1 d . . . . .
C1 C 0.6623(4) 0.6179(3) 0.8030(3) 0.0119(6) Uani 1 1 d . . . . .
C2 C 0.6280(4) 0.6056(3) 0.9293(3) 0.0149(6) Uani 1 1 d . . . . .
H9A H 0.614942 0.527414 0.947272 0.022 Uiso 1 1 calc R U . . .
H9B H 0.729715 0.636638 0.983606 0.022 Uiso 1 1 calc R U . . .
H9C H 0.517065 0.644864 0.938860 0.022 Uiso 1 1 calc R U . . .
N1 N 0.7130(3) 0.5494(2) 0.6212(2) 0.0106(5) Uani 1 1 d . . . . .
N2 N 0.6747(4) 0.5273(2) 0.7364(2) 0.0127(5) Uani 1 1 d . . . . .
O2 O 0.8254(3) 0.67581(18) 0.45059(19) 0.0140(5) Uani 1 1 d . . . . .
O1 O 0.6841(3) 0.71309(17) 0.75834(19) 0.0139(5) Uani 1 1 d . . . . .
O4 O 0.5214(3) 0.7705(2) 0.5267(2) 0.0224(5) Uani 1 1 d . . . . .
O3 O 0.8564(3) 0.83738(19) 0.6237(2) 0.0192(5) Uani 1 1 d . . . . .
V1 V 0.72470(7) 0.72803(4) 0.58466(5) 0.01132(17) Uani 1 1 d . . . . .
H10 H 0.673(5) 0.465(3) 0.764(3) 0.012(9) Uiso 1 1 d . . . . .
H11 H 0.727(5) 0.390(3) 0.583(3) 0.016(9) Uiso 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C5 O2 1.351(2) . ?
C5 C6 1.3900 . ?
C5 C4 1.3900 . ?
C6 C7 1.3900 . ?
C6 H2 0.9300 . ?
C7 C8 1.3900 . ?
C7 H3 0.9300 . ?
C8 C9 1.3900 . ?
C8 H4 0.9300 . ?
C9 C4 1.3900 . ?
C9 H5 0.9300 . ?
C4 C3 1.445(3) . ?
C3 N1 1.300(4) . ?
C3 H11 0.94(4) . ?
C1 O1 1.258(4) . ?
C1 N2 1.322(4) . ?
C1 C2 1.480(4) . ?
C2 H9A 0.9600 . ?
C2 H9B 0.9600 . ?
C2 H9C 0.9600 . ?
N1 N2 1.386(3) . ?
N1 V1 2.169(3) . ?
N2 H10 0.81(4) . ?
O2 V1 1.879(2) . ?
O1 V1 2.019(2) . ?
O4 V1 1.614(2) . ?
O3 V1 1.639(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
O2 C5 C6 117.61(15) . . ?
O2 C5 C4 122.16(15) . . ?
C6 C5 C4 120.0 . . ?
C5 C6 C7 120.0 . . ?
C5 C6 H2 120.0 . . ?
C7 C6 H2 120.0 . . ?
C8 C7 C6 120.0 . . ?
C8 C7 H3 120.0 . . ?
C6 C7 H3 120.0 . . ?
C7 C8 C9 120.0 . . ?
C7 C8 H4 120.0 . . ?
C9 C8 H4 120.0 . . ?
C4 C9 C8 120.0 . . ?
C4 C9 H5 120.0 . . ?
C8 C9 H5 120.0 . . ?
C9 C4 C5 120.0 . . ?
C9 C4 C3 117.37(17) . . ?
C5 C4 C3 122.63(17) . . ?
N1 C3 C4 122.3(3) . . ?
N1 C3 H11 120(2) . . ?
C4 C3 H11 118(2) . . ?
O1 C1 N2 119.0(3) . . ?
O1 C1 C2 121.3(3) . . ?
N2 C1 C2 119.7(3) . . ?
C1 C2 H9A 109.5 . . ?
C1 C2 H9B 109.5 . . ?
H9A C2 H9B 109.5 . . ?
C1 C2 H9C 109.5 . . ?
H9A C2 H9C 109.5 . . ?
H9B C2 H9C 109.5 . . ?
C3 N1 N2 117.4(3) . . ?
C3 N1 V1 130.2(2) . . ?
N2 N1 V1 112.37(18) . . ?
C1 N2 N1 114.3(3) . . ?
C1 N2 H10 122(2) . . ?
N1 N2 H10 123(2) . . ?
C5 O2 V1 136.65(16) . . ?
C1 O1 V1 120.59(19) . . ?
O4 V1 O3 109.23(13) . . ?
O4 V1 O2 103.83(11) . . ?
O3 V1 O2 100.63(10) . . ?
O4 V1 O1 98.41(10) . . ?
O3 V1 O1 89.10(10) . . ?
O2 V1 O1 151.05(9) . . ?
O4 V1 N1 108.72(11) . . ?
O3 V1 N1 140.07(11) . . ?
O2 V1 N1 81.88(9) . . ?
O1 V1 N1 73.51(9) . . ?

_refine_diff_density_max         0.785
_refine_diff_density_min         -0.446
_refine_diff_density_rms         0.106

