# 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_H2L2
_database_code_depnum_ccdc_archive 'CCDC 1851470'
_audit_update_record             
;
2018-06-25 deposited with the CCDC.	2020-01-31 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            'C16 H17 N3 O2'
_chemical_formula_weight         283.32

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'

_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                   8.4314(10)
_cell_length_b                   7.1284(10)
_cell_length_c                   23.591(3)
_cell_angle_alpha                90
_cell_angle_beta                 91.638(12)
_cell_angle_gamma                90
_cell_volume                     1417.3(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    6240
_cell_measurement_theta_min      3.46
_cell_measurement_theta_max      25.00
_exptl_crystal_description       needle
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.06
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.328
_exptl_crystal_F_000             600
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_absorpt_coefficient_mu    0.090
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_process_details   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_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            6240
_diffrn_reflns_av_unetI/netI     0.0509
_diffrn_reflns_av_R_equivalents  0.0407
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_theta_min         3.456
_diffrn_reflns_theta_max         24.996
_diffrn_reflns_theta_full        24.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             2482
_reflns_number_gt                2201
_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       'Crysalis, Oxford Diffraction'
_computing_cell_refinement       'Crysalis, Oxford Diffraction'
_computing_data_reduction        'Crysalis, Oxford Diffraction'
_computing_structure_solution    'SHELXS (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL (Sheldrick, 2008)'
_computing_molecular_graphics    PLATON(Spek,2004)
_computing_publication_material  'SHELXL, PLATON, WINGX (Ferrugia, 2012)'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0584P)²+3.3759P] 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         2482
_refine_ls_number_parameters     206
_refine_ls_number_restraints     4
_refine_ls_R_factor_all          0.1167
_refine_ls_R_factor_gt           0.1044
_refine_ls_wR_factor_ref         0.2305
_refine_ls_wR_factor_gt          0.2240
_refine_ls_goodness_of_fit_ref   1.251
_refine_ls_restrained_S_all      1.251
_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 0.0861(4) 0.6036(6) 0.07969(17) 0.0244(9) Uani 1 1 d . . . . .
C2 C 0.0852(5) 0.4293(6) 0.10861(18) 0.0295(10) Uani 1 1 d . . . . .
C3 C 0.0014(5) 0.4127(7) 0.1582(2) 0.0387(12) Uani 1 1 d . . . . .
H3 H 0.000248 0.297586 0.176738 0.046 Uiso 1 1 calc R U . . .
C4 C -0.0796(5) 0.5600(7) 0.1806(2) 0.0381(11) Uani 1 1 d . . . . .
H4 H -0.134889 0.543919 0.213827 0.046 Uiso 1 1 calc R U . . .
C5 C -0.0795(5) 0.7368(7) 0.15347(19) 0.0327(11) Uani 1 1 d . . . . .
C6 C 0.0030(5) 0.7526(6) 0.10364(18) 0.0287(10) Uani 1 1 d . . . . .
H6 H 0.003135 0.867918 0.085222 0.034 Uiso 1 1 calc R U . . .
C7 C 0.1703(5) 0.6262(6) 0.02642(17) 0.0236(9) Uani 1 1 d . . . . .
C8 C 0.4056(5) 0.3199(6) -0.05400(17) 0.0249(9) Uani 1 1 d . . . . .
C9 C 0.4865(4) 0.3173(6) -0.10843(16) 0.0227(9) Uani 1 1 d . . . . .
C10 C 0.5593(5) 0.1504(6) -0.12803(17) 0.0268(10) Uani 1 1 d . . . . .
C11 C 0.6363(5) 0.1536(7) -0.17944(19) 0.0339(11) Uani 1 1 d . . . . .
H11 H 0.683402 0.044348 -0.192402 0.041 Uiso 1 1 calc R U . . .
C12 C 0.6444(5) 0.3138(7) -0.21148(19) 0.0378(11) Uani 1 1 d . . . . .
H12 H 0.696005 0.312233 -0.245802 0.045 Uiso 1 1 calc R U . . .
C13 C 0.5754(5) 0.4780(7) -0.19248(19) 0.0380(11) Uani 1 1 d . . . . .
H13 H 0.580807 0.587143 -0.213957 0.046 Uiso 1 1 calc R U . . .
C14 C 0.5000(5) 0.4789(6) -0.14250(19) 0.0316(10) Uani 1 1 d . . . . .
H14 H 0.455440 0.590426 -0.130157 0.038 Uiso 1 1 calc R U . . .
C15 C 0.1710(6) 0.8107(6) -0.00454(19) 0.0348(11) Uani 1 1 d . . . . .
H15A H 0.263098 0.817796 -0.027430 0.052 Uiso 1 1 calc R U . . .
H15B H 0.173039 0.911576 0.022422 0.052 Uiso 1 1 calc R U . . .
H15C H 0.077121 0.820412 -0.028387 0.052 Uiso 1 1 calc R U . . .
C16 C -0.1658(6) 0.9016(7) 0.1782(2) 0.0418(12) Uani 1 1 d . . . . .
H16A H -0.101110 0.957410 0.207793 0.063 Uiso 1 1 calc R U . . .
H16B H -0.263954 0.859664 0.193517 0.063 Uiso 1 1 calc R U . . .
H16C H -0.187384 0.992746 0.149016 0.063 Uiso 1 1 calc R U . . .
N1 N 0.2416(4) 0.4787(5) 0.00848(14) 0.0251(8) Uani 1 1 d . . . . .
N2 N 0.3227(4) 0.4799(5) -0.04115(15) 0.0263(8) Uani 1 1 d D . . . .
H2 H 0.322(8) 0.562(7) -0.067(2) 0.08(2) Uiso 1 1 d D . . . .
N3 N 0.5505(5) -0.0183(5) -0.09917(16) 0.0357(10) Uani 1 1 d D . . . .
O1 O 0.1621(4) 0.2740(4) 0.09012(14) 0.0347(8) Uani 1 1 d D . . . .
O2 O 0.4110(4) 0.1893(4) -0.01965(14) 0.0411(9) Uani 1 1 d . . . . .
H3B H 0.617(5) -0.105(6) -0.108(2) 0.049 Uiso 1 1 d D U . . .
H3A H 0.521(6) -0.025(8) -0.0642(11) 0.049 Uiso 1 1 d D U . . .
H1 H 0.196(6) 0.309(8) 0.0575(13) 0.059(18) 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
C1 C6 1.400(6) . ?
C1 C2 1.418(6) . ?
C1 C7 1.470(6) . ?
C2 O1 1.361(5) . ?
C2 C3 1.389(6) . ?
C3 C4 1.368(7) . ?
C3 H3 0.9300 . ?
C4 C5 1.413(7) . ?
C4 H4 0.9300 . ?
C5 C6 1.388(6) . ?
C5 C16 1.509(6) . ?
C6 H6 0.9300 . ?
C7 N1 1.289(5) . ?
C7 C15 1.504(6) . ?
C8 O2 1.235(5) . ?
C8 N2 1.376(5) . ?
C8 C9 1.471(6) . ?
C9 C14 1.411(6) . ?
C9 C10 1.422(6) . ?
C10 N3 1.385(6) . ?
C10 C11 1.392(6) . ?
C11 C12 1.372(7) . ?
C11 H11 0.9300 . ?
C12 C13 1.388(7) . ?
C12 H12 0.9300 . ?
C13 C14 1.355(6) . ?
C13 H13 0.9300 . ?
C14 H14 0.9300 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
N1 N2 1.372(5) . ?
N2 H2 0.85(2) . ?
N3 H3B 0.86(2) . ?
N3 H3A 0.87(2) . ?
O1 H1 0.87(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
C6 C1 C2 117.4(4) . . ?
C6 C1 C7 121.4(4) . . ?
C2 C1 C7 121.1(4) . . ?
O1 C2 C3 117.4(4) . . ?
O1 C2 C1 123.3(4) . . ?
C3 C2 C1 119.3(4) . . ?
C4 C3 C2 122.2(5) . . ?
C4 C3 H3 118.9 . . ?
C2 C3 H3 118.9 . . ?
C3 C4 C5 120.2(4) . . ?
C3 C4 H4 119.9 . . ?
C5 C4 H4 119.9 . . ?
C6 C5 C4 117.6(4) . . ?
C6 C5 C16 121.6(4) . . ?
C4 C5 C16 120.8(4) . . ?
C5 C6 C1 123.3(4) . . ?
C5 C6 H6 118.3 . . ?
C1 C6 H6 118.3 . . ?
N1 C7 C1 115.6(4) . . ?
N1 C7 C15 123.1(4) . . ?
C1 C7 C15 121.3(4) . . ?
O2 C8 N2 119.3(4) . . ?
O2 C8 C9 123.6(4) . . ?
N2 C8 C9 117.0(4) . . ?
C14 C9 C10 117.1(4) . . ?
C14 C9 C8 122.3(4) . . ?
C10 C9 C8 120.7(4) . . ?
N3 C10 C11 118.4(4) . . ?
N3 C10 C9 122.5(4) . . ?
C11 C10 C9 119.1(4) . . ?
C12 C11 C10 121.7(4) . . ?
C12 C11 H11 119.1 . . ?
C10 C11 H11 119.1 . . ?
C11 C12 C13 119.7(4) . . ?
C11 C12 H12 120.1 . . ?
C13 C12 H12 120.1 . . ?
C14 C13 C12 119.7(4) . . ?
C14 C13 H13 120.1 . . ?
C12 C13 H13 120.1 . . ?
C13 C14 C9 122.7(4) . . ?
C13 C14 H14 118.7 . . ?
C9 C14 H14 118.7 . . ?
C7 C15 H15A 109.5 . . ?
C7 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C7 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C5 C16 H16A 109.5 . . ?
C5 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C5 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C7 N1 N2 121.6(3) . . ?
N1 N2 C8 116.8(3) . . ?
N1 N2 H2 129(5) . . ?
C8 N2 H2 114(5) . . ?
C10 N3 H3B 118(4) . . ?
C10 N3 H3A 122(4) . . ?
H3B N3 H3A 113(5) . . ?
C2 O1 H1 103(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
C15 H15C O1 0.96 2.54 3.464(6) 160.5 3_565
N3 H3B O1 0.86(2) 2.25(3) 3.035(5) 152(5) 3_655
N3 H3A O2 0.87(2) 2.08(4) 2.687(5) 126(4) .
N3 H3A O2 0.87(2) 2.36(4) 3.065(5) 139(4) 3_655
O1 H1 N1 0.87(2) 1.72(3) 2.522(5) 152(6) .

_refine_diff_density_max         0.265
_refine_diff_density_min         -0.261
_refine_diff_density_rms         0.060

####################################################################### 
# 
# 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_8
_database_code_depnum_ccdc_archive 'CCDC 1851476'
_audit_update_record             
;
2018-06-25 deposited with the CCDC.	2020-01-31 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            'C32 H30 Cl2 N6 O8 V2'
_chemical_formula_weight         799.40

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'
Cl Cl 0.1484 0.1585 '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                   6.8992(8)
_cell_length_b                   10.7180(12)
_cell_length_c                   11.0208(12)
_cell_angle_alpha                103.797(9)
_cell_angle_beta                 92.767(9)
_cell_angle_gamma                91.011(9)
_cell_volume                     790.15(16)
_cell_formula_units_Z            1
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.680
_exptl_crystal_F_000             408
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_absorpt_coefficient_mu    0.825
_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      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            5601
_diffrn_reflns_av_unetI/netI     0.0877
_diffrn_reflns_av_R_equivalents  0.0362
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         3.431
_diffrn_reflns_theta_max         30.000
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.956
_diffrn_measured_fraction_theta_full 0.981
_diffrn_reflns_Laue_measured_fraction_max 0.956
_diffrn_reflns_Laue_measured_fraction_full 0.981
_diffrn_reflns_point_group_measured_fraction_max 0.956
_diffrn_reflns_point_group_measured_fraction_full 0.981
_reflns_number_total             4414
_reflns_number_gt                3316
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_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)+(0.0821P)²+1.3159P] 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         4414
_refine_ls_number_parameters     234
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0910
_refine_ls_R_factor_gt           0.0673
_refine_ls_wR_factor_ref         0.2044
_refine_ls_wR_factor_gt          0.1897
_refine_ls_goodness_of_fit_ref   1.102
_refine_ls_restrained_S_all      1.101
_refine_ls_shift/su_max          0.095
_refine_ls_shift/su_mean         0.001

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 0.26254(10) 0.62234(7) 0.26988(6) 0.01695(19) Uani 1 1 d . . . . .
Cl Cl 0.49047(19) -0.03711(11) 0.28952(11) 0.0309(3) Uani 1 1 d . . . . .
O1 O 0.2690(4) 0.4960(3) 0.3552(2) 0.0175(6) Uani 1 1 d . . . . .
O2 O 0.1656(4) 0.6904(3) 0.1332(3) 0.0183(6) Uani 1 1 d . . . . .
O3 O 0.4844(4) 0.6676(3) 0.2780(3) 0.0245(7) Uani 1 1 d . . . . .
O4 O 0.1437(5) 0.7455(3) 0.3727(3) 0.0276(7) Uani 1 1 d . . . . .
N1 N 0.2781(4) 0.4699(3) 0.1118(3) 0.0143(6) Uani 1 1 d . . . . .
N2 N 0.2457(5) 0.5045(3) -0.0015(3) 0.0163(7) Uani 1 1 d . . . . .
N3 N 0.1231(6) 0.4830(4) -0.2451(3) 0.0238(8) Uani 1 1 d D . . . .
H3A H 0.189(6) 0.455(5) -0.191(4) 0.029 Uiso 1 1 d D U . . .
H3B H 0.142(7) 0.469(5) -0.323(2) 0.029 Uiso 1 1 d D U . . .
C1 C 0.3541(5) 0.2997(4) 0.2143(4) 0.0153(7) Uani 1 1 d . . . . .
C2 C 0.3343(5) 0.3772(4) 0.3356(4) 0.0157(7) Uani 1 1 d . . . . .
C3 C 0.3771(6) 0.3287(4) 0.4401(4) 0.0192(8) Uani 1 1 d . . . . .
H3 H 0.371928 0.382175 0.519794 0.023 Uiso 1 1 calc R U . . .
C4 C 0.4271(6) 0.2018(4) 0.4268(4) 0.0215(8) Uani 1 1 d . . . . .
H4 H 0.455771 0.169857 0.496803 0.026 Uiso 1 1 calc R U . . .
C5 C 0.4338(6) 0.1235(4) 0.3079(4) 0.0210(8) Uani 1 1 d . . . . .
C6 C 0.4009(6) 0.1709(4) 0.2034(4) 0.0189(8) Uani 1 1 d . . . . .
H6 H 0.409724 0.116632 0.124438 0.023 Uiso 1 1 calc R U . . .
C7 C 0.3187(5) 0.3488(4) 0.1021(4) 0.0163(7) Uani 1 1 d . . . . .
C8 C 0.1898(5) 0.6220(4) 0.0197(4) 0.0157(7) Uani 1 1 d . . . . .
C9 C 0.1570(5) 0.6845(4) -0.0845(4) 0.0165(7) Uani 1 1 d . . . . .
C10 C 0.1369(5) 0.6166(4) -0.2109(4) 0.0183(8) Uani 1 1 d . . . . .
C11 C 0.1167(6) 0.6864(5) -0.3036(4) 0.0232(9) Uani 1 1 d . . . . .
H11 H 0.108541 0.642461 -0.387419 0.028 Uiso 1 1 calc R U . . .
C12 C 0.1088(6) 0.8178(5) -0.2729(4) 0.0265(10) Uani 1 1 d . . . . .
H12 H 0.095342 0.861743 -0.335998 0.032 Uiso 1 1 calc R U . . .
C13 C 0.1205(6) 0.8857(5) -0.1493(4) 0.0253(9) Uani 1 1 d . . . . .
H13 H 0.111574 0.974710 -0.128832 0.030 Uiso 1 1 calc R U . . .
C14 C 0.1458(6) 0.8197(4) -0.0560(4) 0.0201(8) Uani 1 1 d . . . . .
H14 H 0.155507 0.865459 0.027232 0.024 Uiso 1 1 calc R U . . .
C15 C 0.3292(6) 0.2609(4) -0.0254(4) 0.0202(8) Uani 1 1 d . . . . .
H15A H 0.200488 0.241430 -0.063123 0.030 Uiso 1 1 calc R U . . .
H15B H 0.389577 0.182830 -0.018102 0.030 Uiso 1 1 calc R U . . .
H15C H 0.404312 0.302205 -0.076575 0.030 Uiso 1 1 calc R U . . .
C16 C 0.0053(9) 0.8357(6) 0.3688(6) 0.0491(16) Uani 1 1 d . . . . .
H16A H 0.064646 0.920224 0.393820 0.074 Uiso 1 1 calc R U . . .
H16B H -0.094189 0.827755 0.424709 0.074 Uiso 1 1 calc R U . . .
H16C H -0.051050 0.821942 0.285138 0.074 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 O3 1.590(3) . ?
V1 O4 1.764(3) . ?
V1 O1 1.823(3) . ?
V1 O2 1.922(3) . ?
V1 N1 2.093(3) . ?
V1 N3 2.847(4) 2_565 ?
Cl C5 1.738(4) . ?
O1 C2 1.330(5) . ?
O2 C8 1.311(5) . ?
O4 C16 1.378(6) . ?
N1 C7 1.313(5) . ?
N1 N2 1.394(4) . ?
N2 C8 1.294(5) . ?
N3 C10 1.391(6) . ?
N3 H3A 0.851(19) . ?
N3 H3B 0.859(19) . ?
C1 C6 1.402(6) . ?
C1 C2 1.410(5) . ?
C1 C7 1.467(5) . ?
C2 C3 1.394(5) . ?
C3 C4 1.384(6) . ?
C3 H3 0.9300 . ?
C4 C5 1.381(6) . ?
C4 H4 0.9300 . ?
C5 C6 1.375(6) . ?
C6 H6 0.9300 . ?
C7 C15 1.499(5) . ?
C8 C9 1.472(5) . ?
C9 C10 1.408(6) . ?
C9 C14 1.412(6) . ?
C10 C11 1.406(6) . ?
C11 C12 1.371(7) . ?
C11 H11 0.9300 . ?
C12 C13 1.381(7) . ?
C12 H12 0.9300 . ?
C13 C14 1.387(6) . ?
C13 H13 0.9300 . ?
C14 H14 0.9300 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 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
O3 V1 O4 106.17(16) . . ?
O3 V1 O1 102.30(15) . . ?
O4 V1 O1 102.07(14) . . ?
O3 V1 O2 100.30(15) . . ?
O4 V1 O2 88.59(14) . . ?
O1 V1 O2 151.09(13) . . ?
O3 V1 N1 96.51(14) . . ?
O4 V1 N1 154.36(15) . . ?
O1 V1 N1 84.21(13) . . ?
O2 V1 N1 75.51(12) . . ?
O3 V1 N3 174.51(14) . 2_565 ?
O4 V1 N3 79.06(14) . 2_565 ?
O1 V1 N3 74.63(12) . 2_565 ?
O2 V1 N3 81.29(12) . 2_565 ?
N1 V1 N3 78.74(12) . 2_565 ?
C2 O1 V1 136.1(2) . . ?
C8 O2 V1 117.3(3) . . ?
C16 O4 V1 139.5(3) . . ?
C7 N1 N2 115.1(3) . . ?
C7 N1 V1 130.7(3) . . ?
N2 N1 V1 114.1(2) . . ?
C8 N2 N1 109.5(3) . . ?
C10 N3 V1 114.8(2) . 2_565 ?
C10 N3 H3A 108(4) . . ?
V1 N3 H3A 110(4) 2_565 . ?
C10 N3 H3B 101(4) . . ?
V1 N3 H3B 97(4) 2_565 . ?
H3A N3 H3B 126(5) . . ?
C6 C1 C2 117.6(4) . . ?
C6 C1 C7 120.4(4) . . ?
C2 C1 C7 121.9(4) . . ?
O1 C2 C3 117.6(4) . . ?
O1 C2 C1 122.2(3) . . ?
C3 C2 C1 120.2(4) . . ?
C4 C3 C2 120.8(4) . . ?
C4 C3 H3 119.6 . . ?
C2 C3 H3 119.6 . . ?
C5 C4 C3 118.9(4) . . ?
C5 C4 H4 120.6 . . ?
C3 C4 H4 120.6 . . ?
C6 C5 C4 121.2(4) . . ?
C6 C5 Cl 119.3(3) . . ?
C4 C5 Cl 119.5(3) . . ?
C5 C6 C1 121.0(4) . . ?
C5 C6 H6 119.5 . . ?
C1 C6 H6 119.5 . . ?
N1 C7 C1 120.6(4) . . ?
N1 C7 C15 119.2(4) . . ?
C1 C7 C15 120.2(4) . . ?
N2 C8 O2 121.9(4) . . ?
N2 C8 C9 120.3(3) . . ?
O2 C8 C9 117.8(3) . . ?
C10 C9 C14 118.4(4) . . ?
C10 C9 C8 123.5(4) . . ?
C14 C9 C8 118.1(4) . . ?
N3 C10 C11 119.6(4) . . ?
N3 C10 C9 121.5(4) . . ?
C11 C10 C9 118.8(4) . . ?
C12 C11 C10 121.3(4) . . ?
C12 C11 H11 119.3 . . ?
C10 C11 H11 119.3 . . ?
C11 C12 C13 120.7(4) . . ?
C11 C12 H12 119.7 . . ?
C13 C12 H12 119.7 . . ?
C12 C13 C14 119.2(4) . . ?
C12 C13 H13 120.4 . . ?
C14 C13 H13 120.4 . . ?
C13 C14 C9 121.5(4) . . ?
C13 C14 H14 119.3 . . ?
C9 C14 H14 119.3 . . ?
C7 C15 H15A 109.5 . . ?
C7 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C7 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
O4 C16 H16A 109.5 . . ?
O4 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
O4 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?

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
N3 H3A N2 0.851(19) 2.04(4) 2.730(5) 137(5) .
N3 H3A O2 0.851(19) 3.05(5) 3.184(5) 91(4) 2_565
N3 H3A O2 0.851(19) 3.05(5) 3.184(5) 91(4) 2_565

_refine_diff_density_max         0.738
_refine_diff_density_min         -0.680
_refine_diff_density_rms         0.115

####################################################################### 
# 
# 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_6
_database_code_depnum_ccdc_archive 'CCDC 1851474'
_audit_update_record             
;
2018-06-25 deposited with the CCDC.	2020-01-31 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            'C17 H18 N3 O4 V'
_chemical_formula_weight         379.28

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                   8.4289(7)
_cell_length_b                   14.4775(9)
_cell_length_c                   14.0191(14)
_cell_angle_alpha                90
_cell_angle_beta                 101.407(9)
_cell_angle_gamma                90
_cell_volume                     1676.9(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.502
_exptl_crystal_F_000             784
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_absorpt_coefficient_mu    0.619
_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      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            8395
_diffrn_reflns_av_unetI/netI     0.0979
_diffrn_reflns_av_R_equivalents  0.0787
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         3.282
_diffrn_reflns_theta_max         27.498
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.925
_diffrn_measured_fraction_theta_full 0.928
_diffrn_reflns_Laue_measured_fraction_max 0.925
_diffrn_reflns_Laue_measured_fraction_full 0.928
_diffrn_reflns_point_group_measured_fraction_max 0.925
_diffrn_reflns_point_group_measured_fraction_full 0.928
_reflns_number_total             3549
_reflns_number_gt                2648
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_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)+(0.0766P)²] 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         3549
_refine_ls_number_parameters     235
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0865
_refine_ls_R_factor_gt           0.0608
_refine_ls_wR_factor_ref         0.1537
_refine_ls_wR_factor_gt          0.1378
_refine_ls_goodness_of_fit_ref   0.929
_refine_ls_restrained_S_all      0.929
_refine_ls_shift/su_max          0.003
_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 0.79251(6) 0.21334(3) 0.02685(4) 0.01845(19) Uani 1 1 d . . . . .
N1 N 0.8184(3) 0.06958(17) 0.0397(2) 0.0179(6) Uani 1 1 d . . . . .
N2 N 0.9304(3) 0.03857(18) 0.1201(2) 0.0212(6) Uani 1 1 d . . . . .
O1 O 0.7422(3) 0.18695(15) -0.10273(18) 0.0233(6) Uani 1 1 d . . . . .
O2 O 0.9718(3) 0.19457(15) 0.13137(18) 0.0241(6) Uani 1 1 d . . . . .
O3 O 0.6287(3) 0.22191(15) 0.06522(19) 0.0265(6) Uani 1 1 d . . . . .
O4 O 0.8618(3) 0.32851(15) 0.01938(18) 0.0223(5) Uani 1 1 d . . . . .
C1 C 0.6273(4) 0.0345(2) -0.1061(3) 0.0193(7) Uani 1 1 d . . . . .
C2 C 0.6371(4) 0.1230(2) -0.1470(3) 0.0205(7) Uani 1 1 d . . . . .
C3 C 0.5395(4) 0.1452(2) -0.2355(3) 0.0255(8) Uani 1 1 d . . . . .
H3 H 0.548197 0.202985 -0.263036 0.031 Uiso 1 1 calc R U . . .
C4 C 0.4290(4) 0.0817(3) -0.2831(3) 0.0279(8) Uani 1 1 d . . . . .
H4 H 0.362921 0.098076 -0.341958 0.033 Uiso 1 1 calc R U . . .
C5 C 0.4141(4) -0.0059(2) -0.2455(3) 0.0238(8) Uani 1 1 d . . . . .
C6 C 0.5134(4) -0.0282(2) -0.1581(3) 0.0225(8) Uani 1 1 d . . . . .
H6 H 0.505118 -0.086760 -0.132325 0.027 Uiso 1 1 calc R U . . .
C7 C 0.7373(4) 0.0066(2) -0.0166(3) 0.0192(7) Uani 1 1 d . . . . .
C8 C 1.0057(4) 0.1096(2) 0.1658(3) 0.0194(7) Uani 1 1 d . . . . .
C9 C 1.1290(4) 0.1006(2) 0.2540(3) 0.0198(7) Uani 1 1 d . . . . .
C10 C 1.1591(4) 0.0159(2) 0.3061(3) 0.0227(8) Uani 1 1 d . . . . .
C11 C 1.2784(4) 0.0153(2) 0.3927(3) 0.0256(8) Uani 1 1 d . . . . .
H11 H 1.299172 -0.039178 0.428181 0.031 Uiso 1 1 calc R U . . .
C12 C 1.3641(4) 0.0937(2) 0.4253(3) 0.0272(8) Uani 1 1 d . . . . .
H12 H 1.441055 0.091734 0.482880 0.033 Uiso 1 1 calc R U . . .
C13 C 1.3370(4) 0.1765(2) 0.3730(3) 0.0268(8) Uani 1 1 d . . . . .
H13 H 1.397319 0.228956 0.394458 0.032 Uiso 1 1 calc R U . . .
C14 C 1.2206(4) 0.1792(2) 0.2898(3) 0.0229(8) Uani 1 1 d . . . . .
H32 H 1.201377 0.234506 0.255782 0.028 Uiso 1 1 calc R U . . .
N3 N 1.0756(4) -0.0636(2) 0.2769(3) 0.0279(7) Uani 1 1 d . . . . .
H3B H 1.116(4) -0.108(3) 0.313(3) 0.033 Uiso 1 1 d . U . . .
H3A H 1.001(5) -0.065(3) 0.223(3) 0.033 Uiso 1 1 d . U . . .
C15 C 0.7586(4) -0.0939(2) 0.0114(3) 0.0265(8) Uani 1 1 d . . . . .
H15A H 0.870976 -0.106259 0.036543 0.040 Uiso 1 1 calc R U . . .
H15B H 0.721451 -0.131707 -0.044861 0.040 Uiso 1 1 calc R U . . .
H15C H 0.696896 -0.107706 0.060297 0.040 Uiso 1 1 calc R U . . .
C16 C 1.0177(4) 0.3548(3) 0.0044(3) 0.0312(9) Uani 1 1 d . . . . .
H16A H 1.099159 0.322050 0.049368 0.047 Uiso 1 1 calc R U . . .
H16B H 1.032085 0.420028 0.014859 0.047 Uiso 1 1 calc R U . . .
H16C H 1.026998 0.339958 -0.060967 0.047 Uiso 1 1 calc R U . . .
C17 C 0.2944(4) -0.0741(3) -0.3003(3) 0.0314(9) Uani 1 1 d . . . . .
H17A H 0.189476 -0.045833 -0.316529 0.047 Uiso 1 1 calc R U . . .
H17B H 0.288970 -0.127472 -0.260445 0.047 Uiso 1 1 calc R U . . .
H17C H 0.328512 -0.092420 -0.358948 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 O3 1.583(2) . ?
V1 O4 1.777(2) . ?
V1 O1 1.822(2) . ?
V1 O2 1.905(2) . ?
V1 N1 2.097(3) . ?
N1 C7 1.308(4) . ?
N1 N2 1.393(4) . ?
N2 C8 1.307(4) . ?
O1 C2 1.345(4) . ?
O2 C8 1.332(4) . ?
O4 C16 1.422(4) . ?
C1 C2 1.414(4) . ?
C1 C6 1.414(4) . ?
C1 C7 1.462(4) . ?
C2 C3 1.384(5) . ?
C3 C4 1.383(5) . ?
C3 H3 0.9300 . ?
C4 C5 1.389(5) . ?
C4 H4 0.9300 . ?
C5 C6 1.377(5) . ?
C5 C17 1.510(5) . ?
C6 H6 0.9300 . ?
C7 C15 1.508(4) . ?
C8 C9 1.455(5) . ?
C9 C14 1.410(4) . ?
C9 C10 1.425(5) . ?
C10 N3 1.368(4) . ?
C10 C11 1.415(5) . ?
C11 C12 1.375(5) . ?
C11 H11 0.9300 . ?
C12 C13 1.401(5) . ?
C12 H12 0.9300 . ?
C13 C14 1.368(5) . ?
C13 H13 0.9300 . ?
C14 H32 0.9300 . ?
N3 H3B 0.84(4) . ?
N3 H3A 0.89(4) . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 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
O3 V1 O4 105.40(11) . . ?
O3 V1 O1 107.97(12) . . ?
O4 V1 O1 98.77(11) . . ?
O3 V1 O2 111.25(13) . . ?
O4 V1 O2 87.66(10) . . ?
O1 V1 O2 136.86(11) . . ?
O3 V1 N1 97.57(11) . . ?
O4 V1 N1 155.06(11) . . ?
O1 V1 N1 82.96(11) . . ?
O2 V1 N1 74.87(10) . . ?
C7 N1 N2 116.9(3) . . ?
C7 N1 V1 127.4(2) . . ?
N2 N1 V1 115.59(19) . . ?
C8 N2 N1 109.2(2) . . ?
C2 O1 V1 127.3(2) . . ?
C8 O2 V1 119.4(2) . . ?
C16 O4 V1 125.7(2) . . ?
C2 C1 C6 117.5(3) . . ?
C2 C1 C7 121.4(3) . . ?
C6 C1 C7 121.1(3) . . ?
O1 C2 C3 118.3(3) . . ?
O1 C2 C1 121.5(3) . . ?
C3 C2 C1 120.1(3) . . ?
C4 C3 C2 120.2(3) . . ?
C4 C3 H3 119.9 . . ?
C2 C3 H3 119.9 . . ?
C3 C4 C5 121.8(3) . . ?
C3 C4 H4 119.1 . . ?
C5 C4 H4 119.1 . . ?
C6 C5 C4 117.8(3) . . ?
C6 C5 C17 121.8(3) . . ?
C4 C5 C17 120.3(3) . . ?
C5 C6 C1 122.6(3) . . ?
C5 C6 H6 118.7 . . ?
C1 C6 H6 118.7 . . ?
N1 C7 C1 119.5(3) . . ?
N1 C7 C15 119.6(3) . . ?
C1 C7 C15 120.8(3) . . ?
N2 C8 O2 120.0(3) . . ?
N2 C8 C9 122.9(3) . . ?
O2 C8 C9 117.1(3) . . ?
C14 C9 C10 118.9(3) . . ?
C14 C9 C8 118.7(3) . . ?
C10 C9 C8 122.5(3) . . ?
N3 C10 C11 119.2(3) . . ?
N3 C10 C9 122.8(3) . . ?
C11 C10 C9 118.0(3) . . ?
C12 C11 C10 121.2(3) . . ?
C12 C11 H11 119.4 . . ?
C10 C11 H11 119.4 . . ?
C11 C12 C13 120.8(3) . . ?
C11 C12 H12 119.6 . . ?
C13 C12 H12 119.6 . . ?
C14 C13 C12 119.1(3) . . ?
C14 C13 H13 120.5 . . ?
C12 C13 H13 120.5 . . ?
C13 C14 C9 122.1(3) . . ?
C13 C14 H32 119.0 . . ?
C9 C14 H32 119.0 . . ?
C10 N3 H3B 110(3) . . ?
C10 N3 H3A 120(3) . . ?
H3B N3 H3A 129(4) . . ?
C7 C15 H15A 109.5 . . ?
C7 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C7 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
O4 C16 H16A 109.5 . . ?
O4 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
O4 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C5 C17 H17A 109.5 . . ?
C5 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C5 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?

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
N3 H3B O4 0.84(4) 2.50(4) 3.206(4) 142(4) 2_745
N3 H3A N2 0.89(4) 2.08(4) 2.730(4) 130(3) .

_refine_diff_density_max         0.391
_refine_diff_density_min         -0.700
_refine_diff_density_rms         0.084

####################################################################### 
# 
# 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_5
_database_code_depnum_ccdc_archive 'CCDC 1851473'
_audit_update_record             
;
2018-06-25 deposited with the CCDC.	2020-01-31 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            'C16 H16 N3 O4 V'
_chemical_formula_weight         365.26

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'
O O 0.0106 0.0060 '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'
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                   9.7308(4)
_cell_length_b                   13.0374(5)
_cell_length_c                   12.7577(6)
_cell_angle_alpha                90
_cell_angle_beta                 105.085(5)
_cell_angle_gamma                90
_cell_volume                     1562.72(12)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    7670
_cell_measurement_theta_min      2.27
_cell_measurement_theta_max      30.00

_exptl_crystal_description       needle
_exptl_crystal_colour            black
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.05
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.552
_exptl_crystal_F_000             752
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_absorpt_coefficient_mu    0.661
_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  0.936
_exptl_absorpt_correction_T_max  1.000
_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_standards_number         n/a
_diffrn_measurement_device_type  'Oxford Diffaction X-Calibur 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            7670
_diffrn_reflns_av_unetI/netI     0.0595
_diffrn_reflns_av_R_equivalents  0.0268
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.275
_diffrn_reflns_theta_max         29.998
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.965
_diffrn_measured_fraction_theta_full 0.984
_diffrn_reflns_Laue_measured_fraction_max 0.965
_diffrn_reflns_Laue_measured_fraction_full 0.984
_diffrn_reflns_point_group_measured_fraction_max 0.965
_diffrn_reflns_point_group_measured_fraction_full 0.984
_reflns_number_total             4398
_reflns_number_gt                3094
_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       'Crysalis, Oxford Diffraction'
_computing_cell_refinement       'Crysalis, Oxford Diffraction'
_computing_data_reduction        'Crysalis, Oxford Diffraction'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    PLATON(Spek,2004)
_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)+(0.0492P)²] 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         4398
_refine_ls_number_parameters     226
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0633
_refine_ls_R_factor_gt           0.0400
_refine_ls_wR_factor_ref         0.0967
_refine_ls_wR_factor_gt          0.0919
_refine_ls_goodness_of_fit_ref   0.933
_refine_ls_restrained_S_all      0.933
_refine_ls_shift/su_max          0.023
_refine_ls_shift/su_mean         0.001

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 0.72086(3) 0.78891(2) 0.02122(2) 0.01758(9) Uani 1 1 d . . . . .
O1 O 0.81070(13) 0.82805(10) 0.15907(10) 0.0219(3) Uani 1 1 d . . . . .
O2 O 0.54337(13) 0.81192(10) -0.08421(10) 0.0205(3) Uani 1 1 d . . . . .
O3 O 0.84198(14) 0.76233(10) -0.03743(11) 0.0254(3) Uani 1 1 d . . . . .
O4 O 0.64884(13) 0.66960(10) 0.04597(10) 0.0237(3) Uani 1 1 d . . . . .
N1 N 0.71446(15) 0.94572(12) -0.00870(11) 0.0170(3) Uani 1 1 d . . . . .
N2 N 0.60226(15) 0.98054(12) -0.09338(12) 0.0182(3) Uani 1 1 d . . . . .
C1 C 0.92500(18) 0.98521(15) 0.13059(14) 0.0194(4) Uani 1 1 d . . . . .
C2 C 0.91976(19) 0.89483(15) 0.18953(15) 0.0205(4) Uani 1 1 d . . . . .
C3 C 1.0265(2) 0.87232(17) 0.28359(16) 0.0267(5) Uani 1 1 d . . . . .
H13 H 1.020448 0.813527 0.323414 0.032 Uiso 1 1 calc R U . . .
C4 C 1.1414(2) 0.93812(18) 0.31708(16) 0.0298(5) Uani 1 1 d . . . . .
H14 H 1.213043 0.922935 0.379178 0.036 Uiso 1 1 calc R U . . .
C5 C 1.1504(2) 1.02620(18) 0.25885(16) 0.0302(5) Uani 1 1 d . . . . .
H15 H 1.228790 1.069277 0.281186 0.036 Uiso 1 1 calc R U . . .
C6 C 1.0440(2) 1.05030(16) 0.16814(15) 0.0236(4) Uani 1 1 d . . . . .
H16 H 1.050328 1.110567 0.130661 0.028 Uiso 1 1 calc R U . . .
C7 C 0.80815(18) 1.01482(14) 0.03801(14) 0.0177(4) Uani 1 1 d . . . . .
C8 C 0.51726(18) 0.90403(14) -0.12959(14) 0.0171(4) Uani 1 1 d . . . . .
C9 C 0.38925(18) 0.91569(14) -0.22043(14) 0.0179(4) Uani 1 1 d . . . . .
C10 C 0.36140(19) 1.00518(15) -0.28519(15) 0.0205(4) Uani 1 1 d . . . . .
C11 C 0.23759(19) 1.00619(15) -0.37299(15) 0.0241(4) Uani 1 1 d . . . . .
H26 H 0.217855 1.063654 -0.417592 0.029 Uiso 1 1 calc R U . . .
C12 C 0.1462(2) 0.92429(16) -0.39368(15) 0.0237(4) Uani 1 1 d . . . . .
H25 H 0.065313 0.927372 -0.451642 0.028 Uiso 1 1 calc R U . . .
C13 C 0.17251(19) 0.83651(15) -0.32929(15) 0.0225(4) Uani 1 1 d . . . . .
H24 H 0.109738 0.781384 -0.343460 0.027 Uiso 1 1 calc R U . . .
C14 C 0.29348(19) 0.83294(15) -0.24407(15) 0.0207(4) Uani 1 1 d . . . . .
H23 H 0.312154 0.774313 -0.201185 0.025 Uiso 1 1 calc R U . . .
C15 C 0.7942(2) 1.12231(14) -0.00478(16) 0.0238(4) Uani 1 1 d . . . . .
H18A H 0.807184 1.122815 -0.076824 0.036 Uiso 1 1 calc R U . . .
H18B H 0.865101 1.164842 0.041611 0.036 Uiso 1 1 calc R U . . .
H18C H 0.701223 1.148192 -0.006548 0.036 Uiso 1 1 calc R U . . .
C16 C 0.5138(2) 0.6432(2) 0.0565(2) 0.0480(7) Uani 1 1 d . . . . .
H2A H 0.492980 0.682445 0.114135 0.072 Uiso 1 1 calc R U . . .
H2B H 0.511769 0.571425 0.072739 0.072 Uiso 1 1 calc R U . . .
H2C H 0.443909 0.657650 -0.010286 0.072 Uiso 1 1 calc R U . . .
N3 N 0.45127(19) 1.08710(14) -0.26992(15) 0.0291(4) Uani 1 1 d D . . . .
H3A H 0.517(2) 1.0882(19) -0.2144(16) 0.044 Uiso 1 1 d D U . . .
H3B H 0.424(2) 1.1400(14) -0.3064(17) 0.036(7) 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 O3 1.5899(14) . ?
V1 O4 1.7679(14) . ?
V1 O1 1.8213(12) . ?
V1 O2 1.9166(12) . ?
V1 N1 2.0777(15) . ?
O1 C2 1.349(2) . ?
O2 C8 1.329(2) . ?
O4 C16 1.398(2) . ?
N1 C7 1.310(2) . ?
N1 N2 1.3969(18) . ?
N2 C8 1.301(2) . ?
C1 C2 1.406(3) . ?
C1 C6 1.415(2) . ?
C1 C7 1.462(2) . ?
C2 C3 1.399(2) . ?
C3 C4 1.386(3) . ?
C3 H13 0.9300 . ?
C4 C5 1.383(3) . ?
C4 H14 0.9300 . ?
C5 C6 1.373(3) . ?
C5 H15 0.9300 . ?
C6 H16 0.9300 . ?
C7 C15 1.497(3) . ?
C8 C9 1.472(2) . ?
C9 C14 1.406(3) . ?
C9 C10 1.415(3) . ?
C10 N3 1.362(3) . ?
C10 C11 1.416(2) . ?
C11 C12 1.371(3) . ?
C11 H26 0.9300 . ?
C12 C13 1.393(3) . ?
C12 H25 0.9300 . ?
C13 C14 1.380(2) . ?
C13 H24 0.9300 . ?
C14 H23 0.9300 . ?
C15 H18A 0.9600 . ?
C15 H18B 0.9600 . ?
C15 H18C 0.9600 . ?
C16 H2A 0.9600 . ?
C16 H2B 0.9600 . ?
C16 H2C 0.9600 . ?
N3 H3A 0.825(15) . ?
N3 H3B 0.836(15) . ?

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
O3 V1 O4 105.61(7) . . ?
O3 V1 O1 106.69(7) . . ?
O4 V1 O1 100.78(6) . . ?
O3 V1 O2 110.29(6) . . ?
O4 V1 O2 86.35(6) . . ?
O1 V1 O2 138.78(6) . . ?
O3 V1 N1 96.80(7) . . ?
O4 V1 N1 154.72(6) . . ?
O1 V1 N1 83.43(6) . . ?
O2 V1 N1 74.85(5) . . ?
C2 O1 V1 127.07(12) . . ?
C8 O2 V1 118.85(11) . . ?
C16 O4 V1 131.28(14) . . ?
C7 N1 N2 116.09(15) . . ?
C7 N1 V1 127.54(12) . . ?
N2 N1 V1 116.22(10) . . ?
C8 N2 N1 108.79(14) . . ?
C2 C1 C6 117.52(17) . . ?
C2 C1 C7 121.64(16) . . ?
C6 C1 C7 120.73(18) . . ?
O1 C2 C3 117.69(18) . . ?
O1 C2 C1 121.47(16) . . ?
C3 C2 C1 120.82(17) . . ?
C4 C3 C2 119.6(2) . . ?
C4 C3 H13 120.2 . . ?
C2 C3 H13 120.2 . . ?
C5 C4 C3 120.48(18) . . ?
C5 C4 H14 119.8 . . ?
C3 C4 H14 119.8 . . ?
C6 C5 C4 120.23(19) . . ?
C6 C5 H15 119.9 . . ?
C4 C5 H15 119.9 . . ?
C5 C6 C1 121.3(2) . . ?
C5 C6 H16 119.4 . . ?
C1 C6 H16 119.4 . . ?
N1 C7 C1 119.26(17) . . ?
N1 C7 C15 119.44(16) . . ?
C1 C7 C15 121.29(16) . . ?
N2 C8 O2 120.42(15) . . ?
N2 C8 C9 121.99(16) . . ?
O2 C8 C9 117.59(15) . . ?
C14 C9 C10 119.47(16) . . ?
C14 C9 C8 117.87(16) . . ?
C10 C9 C8 122.64(16) . . ?
N3 C10 C9 123.03(16) . . ?
N3 C10 C11 119.24(17) . . ?
C9 C10 C11 117.66(17) . . ?
C12 C11 C10 121.40(17) . . ?
C12 C11 H26 119.3 . . ?
C10 C11 H26 119.3 . . ?
C11 C12 C13 121.06(17) . . ?
C11 C12 H25 119.5 . . ?
C13 C12 H25 119.5 . . ?
C14 C13 C12 118.72(18) . . ?
C14 C13 H24 120.6 . . ?
C12 C13 H24 120.6 . . ?
C13 C14 C9 121.67(17) . . ?
C13 C14 H23 119.2 . . ?
C9 C14 H23 119.2 . . ?
C7 C15 H18A 109.5 . . ?
C7 C15 H18B 109.5 . . ?
H18A C15 H18B 109.5 . . ?
C7 C15 H18C 109.5 . . ?
H18A C15 H18C 109.5 . . ?
H18B C15 H18C 109.5 . . ?
O4 C16 H2A 109.5 . . ?
O4 C16 H2B 109.5 . . ?
H2A C16 H2B 109.5 . . ?
O4 C16 H2C 109.5 . . ?
H2A C16 H2C 109.5 . . ?
H2B C16 H2C 109.5 . . ?
C10 N3 H3A 117.8(18) . . ?
C10 N3 H3B 117.7(16) . . ?
H3A N3 H3B 122(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
N3 H3A N2 0.825(15) 2.09(2) 2.728(2) 134(2) .

_refine_diff_density_max         0.571
_refine_diff_density_min         -0.379
_refine_diff_density_rms         0.072

####################################################################### 
# 
# 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_H2L3
_database_code_depnum_ccdc_archive 'CCDC 1851471'
_audit_update_record             
;
2018-06-25 deposited with the CCDC.	2020-01-31 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            'C16 H17 N3 O3'
_chemical_formula_weight         299.32

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'

_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                   16.7983(14)
_cell_length_b                   7.3360(8)
_cell_length_c                   12.7009(13)
_cell_angle_alpha                90
_cell_angle_beta                 111.721(11)
_cell_angle_gamma                90
_cell_volume                     1454.0(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    6403
_cell_measurement_theta_min      3.48
_cell_measurement_theta_max      30.00



_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.31
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.26
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.367
_exptl_crystal_F_000             632
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_absorpt_coefficient_mu    0.097
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   none
_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            6308
_diffrn_reflns_av_unetI/netI     0.0770
_diffrn_reflns_av_R_equivalents  0.0440
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         3.453
_diffrn_reflns_theta_max         29.996
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.958
_diffrn_measured_fraction_theta_full 0.972
_diffrn_reflns_Laue_measured_fraction_max 0.958
_diffrn_reflns_Laue_measured_fraction_full 0.972
_diffrn_reflns_point_group_measured_fraction_max 0.958
_diffrn_reflns_point_group_measured_fraction_full 0.972
_reflns_number_total             4065
_reflns_number_gt                2444
_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       'Crysalis, Oxford Diffraction'
_computing_cell_refinement       'Crysalis, Oxford Diffraction'
_computing_data_reduction        'Crysalis, Oxford Diffraction'
_computing_structure_solution    'SHELXS (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL (Sheldrick, 2008)'
_computing_molecular_graphics    PLATON(Spek,2004)
_computing_publication_material  'SHELXL, PLATON, WINGX (Ferrugia, 2012)'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0655P)²+0.1706P] 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         4065
_refine_ls_number_parameters     216
_refine_ls_number_restraints     4
_refine_ls_R_factor_all          0.1407
_refine_ls_R_factor_gt           0.0805
_refine_ls_wR_factor_ref         0.1827
_refine_ls_wR_factor_gt          0.1570
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_restrained_S_all      1.037
_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 0.24773(13) 0.1279(3) 0.28459(18) 0.0287(5) Uani 1 1 d . . . . .
C2 C 0.28060(14) 0.1700(3) 0.40143(18) 0.0324(5) Uani 1 1 d . . . . .
C3 C 0.36785(14) 0.1901(4) 0.4584(2) 0.0429(7) Uani 1 1 d . . . . .
H3 H 0.388945 0.216297 0.535534 0.051 Uiso 1 1 calc R U . . .
C4 C 0.42448(16) 0.1720(4) 0.4029(2) 0.0480(7) Uani 1 1 d . . . . .
H4 H 0.4856(17) 0.189(4) 0.446(2) 0.058 Uiso 1 1 d . U . . .
C5 C 0.39338(14) 0.1344(4) 0.2892(2) 0.0423(7) Uani 1 1 d . . . . .
C6 C 0.30622(13) 0.1113(4) 0.2305(2) 0.0354(6) Uani 1 1 d . . . . .
H6 H 0.286248 0.084215 0.153488 0.042 Uiso 1 1 calc R U . . .
C7 C 0.15523(12) 0.1052(3) 0.22033(17) 0.0263(5) Uani 1 1 d . . . . .
C8 C -0.02868(13) 0.1363(3) 0.29020(18) 0.0298(5) Uani 1 1 d . . . . .
C9 C -0.12228(12) 0.1422(3) 0.22826(17) 0.0264(5) Uani 1 1 d . . . . .
C10 C -0.17778(13) 0.0804(3) 0.28133(19) 0.0292(5) Uani 1 1 d . . . . .
C11 C -0.26645(14) 0.0860(4) 0.2183(2) 0.0390(6) Uani 1 1 d . . . . .
H11 H -0.304175 0.043549 0.250937 0.047 Uiso 1 1 calc R U . . .
C12 C -0.29838(15) 0.1525(4) 0.1100(2) 0.0445(7) Uani 1 1 d . . . . .
H12 H -0.357313 0.153932 0.070327 0.053 Uiso 1 1 calc R U . . .
C13 C -0.24437(14) 0.2179(4) 0.0584(2) 0.0407(6) Uani 1 1 d . . . . .
H13 H -0.266477 0.264429 -0.014922 0.049 Uiso 1 1 calc R U . . .
C14 C -0.15758(14) 0.2123(3) 0.11783(19) 0.0327(5) Uani 1 1 d . . . . .
H14 H -0.120995 0.256385 0.083847 0.039 Uiso 1 1 calc R U . . .
C15 C 0.12082(14) 0.0421(4) 0.09955(18) 0.0351(6) Uani 1 1 d . . . . .
H15A H 0.087645 0.137942 0.051897 0.053 Uiso 1 1 calc R U . . .
H15B H 0.085176 -0.062995 0.092589 0.053 Uiso 1 1 calc R U . . .
H15C H 0.167600 0.010951 0.076771 0.053 Uiso 1 1 calc R U . . .
C16 C 0.53282(16) 0.1451(6) 0.2778(3) 0.0815(12) Uani 1 1 d . . . . .
H16A H 0.556514 0.053657 0.334998 0.122 Uiso 1 1 calc R U . . .
H16B H 0.543126 0.263595 0.312307 0.122 Uiso 1 1 calc R U . . .
H16C H 0.559399 0.137079 0.222829 0.122 Uiso 1 1 calc R U . . .
N1 N 0.10695(10) 0.1408(3) 0.27650(15) 0.0311(5) Uani 1 1 d . . . . .
N2 N 0.01932(11) 0.1253(3) 0.22383(16) 0.0347(5) Uani 1 1 d D . . . .
N3 N -0.14956(13) 0.0145(3) 0.38896(17) 0.0401(5) Uani 1 1 d D . . . .
O1 O 0.22987(10) 0.1927(3) 0.46285(13) 0.0421(5) Uani 1 1 d D . . . .
O2 O 0.00599(9) 0.1394(3) 0.39380(13) 0.0444(5) Uani 1 1 d . . . . .
O3 O 0.44285(10) 0.1167(3) 0.22339(17) 0.0643(7) Uani 1 1 d . . . . .
H2 H -0.0044(18) 0.103(5) 0.1540(16) 0.077 Uiso 1 1 d D U . . .
H3A H -0.0951(12) 0.015(5) 0.431(2) 0.077 Uiso 1 1 d D U . . .
H3B H -0.1861(16) -0.037(4) 0.412(3) 0.077 Uiso 1 1 d D U . . .
H1 H 0.1787(14) 0.187(5) 0.413(2) 0.096 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
C1 C6 1.397(3) . ?
C1 C2 1.413(3) . ?
C1 C7 1.473(3) . ?
C2 O1 1.362(3) . ?
C2 C3 1.382(3) . ?
C3 C4 1.384(4) . ?
C3 H3 0.9300 . ?
C4 C5 1.370(4) . ?
C4 H4 0.98(3) . ?
C5 C6 1.386(3) . ?
C5 O3 1.385(3) . ?
C6 H6 0.9300 . ?
C7 N1 1.290(2) . ?
C7 C15 1.498(3) . ?
C8 O2 1.226(2) . ?
C8 N2 1.368(3) . ?
C8 C9 1.476(3) . ?
C9 C14 1.403(3) . ?
C9 C10 1.412(3) . ?
C10 N3 1.359(3) . ?
C10 C11 1.407(3) . ?
C11 C12 1.368(4) . ?
C11 H11 0.9300 . ?
C12 C13 1.387(3) . ?
C12 H12 0.9300 . ?
C13 C14 1.372(3) . ?
C13 H13 0.9300 . ?
C14 H14 0.9300 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C16 O3 1.425(3) . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
N1 N2 1.378(2) . ?
N2 H2 0.843(17) . ?
N3 H3A 0.871(17) . ?
N3 H3B 0.854(17) . ?
O1 H1 0.861(18) . ?

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
C6 C1 C2 117.60(19) . . ?
C6 C1 C7 120.47(19) . . ?
C2 C1 C7 121.93(18) . . ?
O1 C2 C3 117.0(2) . . ?
O1 C2 C1 122.97(18) . . ?
C3 C2 C1 120.0(2) . . ?
C2 C3 C4 121.2(2) . . ?
C2 C3 H3 119.4 . . ?
C4 C3 H3 119.4 . . ?
C5 C4 C3 119.4(2) . . ?
C5 C4 H4 121.5(17) . . ?
C3 C4 H4 119.1(17) . . ?
C4 C5 C6 120.4(2) . . ?
C4 C5 O3 125.1(2) . . ?
C6 C5 O3 114.5(2) . . ?
C5 C6 C1 121.3(2) . . ?
C5 C6 H6 119.3 . . ?
C1 C6 H6 119.3 . . ?
N1 C7 C1 114.89(19) . . ?
N1 C7 C15 123.06(18) . . ?
C1 C7 C15 122.04(18) . . ?
O2 C8 N2 120.54(18) . . ?
O2 C8 C9 124.11(19) . . ?
N2 C8 C9 115.34(18) . . ?
C14 C9 C10 119.04(18) . . ?
C14 C9 C8 121.10(19) . . ?
C10 C9 C8 119.85(19) . . ?
N3 C10 C11 119.0(2) . . ?
N3 C10 C9 123.23(19) . . ?
C11 C10 C9 117.8(2) . . ?
C12 C11 C10 121.4(2) . . ?
C12 C11 H11 119.3 . . ?
C10 C11 H11 119.3 . . ?
C11 C12 C13 121.1(2) . . ?
C11 C12 H12 119.4 . . ?
C13 C12 H12 119.4 . . ?
C14 C13 C12 118.5(2) . . ?
C14 C13 H13 120.8 . . ?
C12 C13 H13 120.8 . . ?
C13 C14 C9 122.1(2) . . ?
C13 C14 H14 119.0 . . ?
C9 C14 H14 119.0 . . ?
C7 C15 H15A 109.5 . . ?
C7 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C7 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
O3 C16 H16A 109.5 . . ?
O3 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
O3 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C7 N1 N2 119.49(18) . . ?
C8 N2 N1 117.61(18) . . ?
C8 N2 H2 120(2) . . ?
N1 N2 H2 122(2) . . ?
C10 N3 H3A 120(2) . . ?
C10 N3 H3B 118(2) . . ?
H3A N3 H3B 121(3) . . ?
C2 O1 H1 104(2) . . ?
C5 O3 C16 117.3(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
N3 H3A O2 0.871(17) 2.13(3) 2.748(2) 128(3) .
N3 H3A O2 0.871(17) 2.45(3) 3.127(3) 134(3) 3_556
N3 H3B O1 0.854(17) 2.30(2) 3.091(3) 155(3) 3_556
O1 H1 N1 0.861(18) 1.74(2) 2.528(2) 152(4) .

_refine_diff_density_max         0.244
_refine_diff_density_min         -0.236
_refine_diff_density_rms         0.049

####################################################################### 
# 
# 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_3
_database_code_depnum_ccdc_archive 'CCDC 1851472'
_audit_update_record             
;
2018-06-25 deposited with the CCDC.	2020-01-31 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            'C32 H30 N6 O6 V'
_chemical_formula_weight         645.56

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           15
_space_group_name_H-M_alt        'I 2/a'
_space_group_name_Hall           '-I 2ya'

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

_cell_length_a                   11.0164(9)
_cell_length_b                   9.5390(9)
_cell_length_c                   27.584(2)
_cell_angle_alpha                90
_cell_angle_beta                 92.035(8)
_cell_angle_gamma                90
_cell_volume                     2896.9(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.480
_exptl_crystal_F_000             1340
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_absorpt_coefficient_mu    0.400
_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      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            4539
_diffrn_reflns_av_unetI/netI     0.1887
_diffrn_reflns_av_R_equivalents  0.1178
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_theta_min         3.158
_diffrn_reflns_theta_max         24.996
_diffrn_reflns_theta_full        24.997
_diffrn_measured_fraction_theta_max 0.941
_diffrn_measured_fraction_theta_full 0.941
_diffrn_reflns_Laue_measured_fraction_max 0.941
_diffrn_reflns_Laue_measured_fraction_full 0.941
_diffrn_reflns_point_group_measured_fraction_max 0.941
_diffrn_reflns_point_group_measured_fraction_full 0.941
_reflns_number_total             2413
_reflns_number_gt                1473
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_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)+(0.0059P)²] 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         2413
_refine_ls_number_parameters     212
_refine_ls_number_restraints     8
_refine_ls_R_factor_all          0.1716
_refine_ls_R_factor_gt           0.1015
_refine_ls_wR_factor_ref         0.1430
_refine_ls_wR_factor_gt          0.1211
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_restrained_S_all      1.059
_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 0.750000 0.12387(17) 0.500000 0.0160(4) Uani 1 2 d S T P . .
O1 O 0.8349(4) -0.0209(4) 0.53238(15) 0.0178(11) Uani 1 1 d . . . . .
O2 O 0.7826(4) 0.1942(4) 0.43714(15) 0.0192(11) Uani 1 1 d . . . . .
O4 O 1.0925(4) 0.0213(5) 0.70582(16) 0.0299(13) Uani 1 1 d . . . . .
N1 N 0.9171(5) 0.2256(5) 0.50746(19) 0.0178(13) Uani 1 1 d . . . . .
N2 N 0.9488(5) 0.3104(5) 0.46841(19) 0.0216(14) Uani 1 1 d . . . . .
N3 N 1.0699(6) 0.4730(7) 0.4052(2) 0.0348(18) Uani 1 1 d D . . . .
H3A H 1.068(6) 0.449(7) 0.4356(10) 0.042 Uiso 1 1 d D U . . .
H3B H 1.130(4) 0.520(7) 0.394(2) 0.042 Uiso 1 1 d D U . . .
C1 C 0.9782(6) 0.1134(7) 0.5814(2) 0.0194(16) Uani 1 1 d . . . . .
C2 C 0.9009(6) -0.0038(7) 0.5732(2) 0.0206(17) Uani 1 1 d . . . . .
C3 C 0.8947(6) -0.1050(7) 0.6089(2) 0.0221(17) Uani 1 1 d . . . . .
H3 H 0.845298 -0.182893 0.603423 0.026 Uiso 1 1 calc R U . . .
C4 C 0.9591(6) -0.0938(7) 0.6520(2) 0.0226(18) Uani 1 1 d . . . . .
H4 H 0.953058 -0.163460 0.675384 0.027 Uiso 1 1 calc R U . . .
C5 C 1.0343(6) 0.0230(7) 0.6610(2) 0.0219(18) Uani 1 1 d . . . . .
C6 C 1.0424(5) 0.1226(7) 0.6262(2) 0.0206(16) Uani 1 1 d . . . . .
H6 H 1.092372 0.199695 0.632154 0.025 Uiso 1 1 calc R U . . .
C7 C 0.9975(6) 0.2154(6) 0.5433(2) 0.0167(16) Uani 1 1 d . U . . .
C8 C 0.8717(6) 0.2842(7) 0.4325(3) 0.0226(17) Uani 1 1 d . . . . .
C9 C 0.8807(6) 0.3521(7) 0.3848(2) 0.0185(17) Uani 1 1 d . . . . .
C10 C 0.9783(6) 0.4393(7) 0.3726(3) 0.0252(18) Uani 1 1 d . . . . .
C11 C 0.9804(7) 0.4910(7) 0.3251(3) 0.033(2) Uani 1 1 d . . . . .
H11 H 1.043006 0.550748 0.316758 0.040 Uiso 1 1 calc R U . . .
C12 C 0.8939(7) 0.4567(8) 0.2910(3) 0.036(2) Uani 1 1 d . . . . .
H12 H 0.899018 0.490742 0.259530 0.043 Uiso 1 1 calc R U . . .
C13 C 0.7975(6) 0.3704(8) 0.3030(2) 0.0302(19) Uani 1 1 d . . . . .
H13 H 0.737561 0.347429 0.279723 0.036 Uiso 1 1 calc R U . . .
C14 C 0.7917(6) 0.3199(7) 0.3491(2) 0.0237(18) Uani 1 1 d . . . . .
H14 H 0.727064 0.262608 0.356988 0.028 Uiso 1 1 calc R U . . .
C15 C 1.1133(5) 0.2977(7) 0.5428(2) 0.0253(18) Uani 1 1 d . . . . .
H15A H 1.178584 0.237199 0.534041 0.038 Uiso 1 1 calc R U . . .
H15B H 1.130499 0.336276 0.574440 0.038 Uiso 1 1 calc R U . . .
H15C H 1.104874 0.372356 0.519583 0.038 Uiso 1 1 calc R U . . .
C16 C 1.1534(6) 0.1459(7) 0.7197(3) 0.038(2) Uani 1 1 d . . . . .
H16A H 1.181213 0.138913 0.752969 0.057 Uiso 1 1 calc R U . . .
H16B H 1.098831 0.223872 0.715946 0.057 Uiso 1 1 calc R U . . .
H16C H 1.221731 0.159591 0.699532 0.057 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 O1 1.876(4) 2_656 ?
V1 O1 1.877(4) . ?
V1 O2 1.905(4) . ?
V1 O2 1.905(4) 2_656 ?
V1 N1 2.085(5) . ?
V1 N1 2.085(5) 2_656 ?
O1 C2 1.329(7) . ?
O2 C8 1.313(7) . ?
O4 C5 1.372(7) . ?
O4 C16 1.411(7) . ?
N1 C7 1.308(7) . ?
N1 N2 1.401(7) . ?
N2 C8 1.306(7) . ?
N3 C10 1.367(9) . ?
N3 H3A 0.87(2) . ?
N3 H3B 0.87(2) . ?
C1 C6 1.405(8) . ?
C1 C2 1.418(9) . ?
C1 C7 1.452(9) . ?
C2 C3 1.382(9) . ?
C3 C4 1.367(8) . ?
C3 H3 0.9300 . ?
C4 C5 1.405(9) . ?
C4 H4 0.9300 . ?
C5 C6 1.357(9) . ?
C6 H6 0.9300 . ?
C7 C15 1.498(8) . ?
C8 C9 1.473(9) . ?
C9 C14 1.399(8) . ?
C9 C10 1.409(9) . ?
C10 C11 1.401(9) . ?
C11 C12 1.356(9) . ?
C11 H11 0.9300 . ?
C12 C13 1.393(9) . ?
C12 H12 0.9300 . ?
C13 C14 1.364(9) . ?
C13 H13 0.9300 . ?
C14 H14 0.9300 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 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
O1 V1 O1 85.2(3) 2_656 . ?
O1 V1 O2 86.17(18) 2_656 . ?
O1 V1 O2 125.84(18) . . ?
O1 V1 O2 125.83(18) 2_656 2_656 ?
O1 V1 O2 86.17(18) . 2_656 ?
O2 V1 O2 138.7(3) . 2_656 ?
O1 V1 N1 144.4(2) 2_656 . ?
O1 V1 N1 82.66(19) . . ?
O2 V1 N1 74.42(19) . . ?
O2 V1 N1 86.6(2) 2_656 . ?
O1 V1 N1 82.65(19) 2_656 2_656 ?
O1 V1 N1 144.4(2) . 2_656 ?
O2 V1 N1 86.60(19) . 2_656 ?
O2 V1 N1 74.42(19) 2_656 2_656 ?
N1 V1 N1 124.5(3) . 2_656 ?
C2 O1 V1 124.1(4) . . ?
C8 O2 V1 119.0(4) . . ?
C5 O4 C16 115.9(5) . . ?
C7 N1 N2 116.3(5) . . ?
C7 N1 V1 127.8(4) . . ?
N2 N1 V1 115.9(4) . . ?
C8 N2 N1 107.4(5) . . ?
C10 N3 H3A 122(5) . . ?
C10 N3 H3B 116(5) . . ?
H3A N3 H3B 121(7) . . ?
C6 C1 C2 118.0(6) . . ?
C6 C1 C7 120.8(6) . . ?
C2 C1 C7 121.0(6) . . ?
O1 C2 C3 118.5(6) . . ?
O1 C2 C1 122.6(6) . . ?
C3 C2 C1 118.8(6) . . ?
C4 C3 C2 121.8(6) . . ?
C4 C3 H3 119.1 . . ?
C2 C3 H3 119.1 . . ?
C3 C4 C5 120.0(6) . . ?
C3 C4 H4 120.0 . . ?
C5 C4 H4 120.0 . . ?
C6 C5 O4 127.3(6) . . ?
C6 C5 C4 118.9(6) . . ?
O4 C5 C4 113.8(6) . . ?
C5 C6 C1 122.4(6) . . ?
C5 C6 H6 118.8 . . ?
C1 C6 H6 118.8 . . ?
N1 C7 C1 118.9(6) . . ?
N1 C7 C15 120.5(6) . . ?
C1 C7 C15 120.3(6) . . ?
N2 C8 O2 121.3(6) . . ?
N2 C8 C9 122.0(6) . . ?
O2 C8 C9 116.7(6) . . ?
C14 C9 C10 118.9(6) . . ?
C14 C9 C8 117.7(6) . . ?
C10 C9 C8 123.3(6) . . ?
N3 C10 C11 119.7(7) . . ?
N3 C10 C9 122.3(6) . . ?
C11 C10 C9 118.0(6) . . ?
C12 C11 C10 122.0(7) . . ?
C12 C11 H11 119.0 . . ?
C10 C11 H11 119.0 . . ?
C11 C12 C13 120.1(7) . . ?
C11 C12 H12 120.0 . . ?
C13 C12 H12 120.0 . . ?
C14 C13 C12 119.4(7) . . ?
C14 C13 H13 120.3 . . ?
C12 C13 H13 120.3 . . ?
C13 C14 C9 121.6(7) . . ?
C13 C14 H14 119.2 . . ?
C9 C14 H14 119.2 . . ?
C7 C15 H15A 109.5 . . ?
C7 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C7 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
O4 C16 H16A 109.5 . . ?
O4 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
O4 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?

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
N3 H3A N2 0.87(2) 2.09(6) 2.719(9) 128(6) .

_refine_diff_density_max         0.359
_refine_diff_density_min         -0.355
_refine_diff_density_rms         0.086

####################################################################### 
# 
# 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_7
_database_code_depnum_ccdc_archive 'CCDC 1851475'
_audit_update_record             
;
2018-06-25 deposited with the CCDC.	2020-01-31 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            'C17 H18 N3 O5 V'
_chemical_formula_weight         395.27

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'
O O 0.0106 0.0060 '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'
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                   8.9923(2)
_cell_length_b                   12.1935(3)
_cell_length_c                   15.8556(5)
_cell_angle_alpha                90
_cell_angle_beta                 104.014(3)
_cell_angle_gamma                90
_cell_volume                     1686.78(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.501
_exptl_crystal_F_000             788
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_absorpt_coefficient_mu    0.619
_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      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            8918
_diffrn_reflns_av_unetI/netI     0.0440
_diffrn_reflns_av_R_equivalents  0.0246
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         2.871
_diffrn_reflns_theta_max         29.999
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.965
_diffrn_measured_fraction_theta_full 0.973
_diffrn_reflns_Laue_measured_fraction_max 0.965
_diffrn_reflns_Laue_measured_fraction_full 0.973
_diffrn_reflns_point_group_measured_fraction_max 0.965
_diffrn_reflns_point_group_measured_fraction_full 0.973
_reflns_number_total             4740
_reflns_number_gt                3656
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_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)+(0.0519P)²] 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         4740
_refine_ls_number_parameters     244
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0469
_refine_ls_R_factor_gt           0.0342
_refine_ls_wR_factor_ref         0.0915
_refine_ls_wR_factor_gt          0.0891
_refine_ls_goodness_of_fit_ref   0.975
_refine_ls_restrained_S_all      0.975
_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 0.31200(3) 0.43127(2) 0.79157(2) 0.01459(8) Uani 1 1 d . . . . .
O1 O 0.45657(12) 0.36561(8) 0.74347(7) 0.0174(2) Uani 1 1 d . . . . .
O2 O 0.25563(12) 0.49819(9) 0.89099(7) 0.0175(2) Uani 1 1 d . . . . .
O3 O 0.23603(13) 0.51477(9) 0.71693(7) 0.0221(3) Uani 1 1 d . . . . .
O4 O 0.16876(12) 0.32764(8) 0.78046(7) 0.0176(2) Uani 1 1 d . . . . .
O5 O 0.82780(15) 0.58379(10) 0.56880(8) 0.0269(3) Uani 1 1 d . . . . .
N1 N 0.49690(15) 0.53787(10) 0.84813(8) 0.0140(3) Uani 1 1 d . . . . .
N2 N 0.48210(15) 0.59333(10) 0.92254(8) 0.0146(3) Uani 1 1 d . . . . .
N3 N 0.55012(15) 0.69560(11) 1.08398(9) 0.0165(3) Uani 1 1 d . . . . .
H3B H 0.589(2) 0.7522(15) 1.1046(12) 0.020 Uiso 1 1 d . U . . .
H3A H 0.576(2) 0.6766(15) 1.0399(13) 0.020 Uiso 1 1 d . U . . .
C1 C 0.63204(17) 0.51324(12) 0.73742(10) 0.0151(3) Uani 1 1 d . . . . .
C2 C 0.55323(17) 0.41660(12) 0.70322(10) 0.0156(3) Uani 1 1 d . . . . .
C3 C 0.57844(18) 0.37160(13) 0.62724(11) 0.0202(3) Uani 1 1 d . . . . .
H3 H 0.533344 0.304830 0.607344 0.024 Uiso 1 1 calc R U . . .
C4 C 0.6693(2) 0.42420(13) 0.58064(11) 0.0218(3) Uani 1 1 d . . . . .
H4 H 0.683243 0.393792 0.529310 0.026 Uiso 1 1 calc R U . . .
C5 C 0.73987(18) 0.52336(13) 0.61139(10) 0.0186(3) Uani 1 1 d . . . . .
C6 C 0.72552(17) 0.56441(12) 0.68992(10) 0.0165(3) Uani 1 1 d . . . . .
H6 H 0.779020 0.627530 0.712015 0.020 Uiso 1 1 calc R U . . .
C7 C 0.61719(17) 0.56087(11) 0.81952(10) 0.0146(3) Uani 1 1 d . . . . .
C8 C 0.34888(17) 0.57012(11) 0.93724(10) 0.0147(3) Uani 1 1 d . . . . .
C9 C 0.29437(17) 0.63035(12) 1.00474(10) 0.0150(3) Uani 1 1 d . . . . .
C10 C 0.38895(17) 0.69729(11) 1.06842(10) 0.0149(3) Uani 1 1 d . . . . .
C11 C 0.32080(19) 0.76252(12) 1.12089(10) 0.0184(3) Uani 1 1 d . . . . .
H11 H 0.381673 0.809099 1.161426 0.022 Uiso 1 1 calc R U . . .
C12 C 0.16477(19) 0.75927(13) 1.11379(11) 0.0215(3) Uani 1 1 d . . . . .
H12 H 0.121348 0.804824 1.148347 0.026 Uiso 1 1 calc R U . . .
C13 C 0.07257(19) 0.68832(14) 1.05529(12) 0.0249(4) Uani 1 1 d . . . . .
H13 H -0.031728 0.683341 1.052468 0.030 Uiso 1 1 calc R U . . .
C14 C 0.13735(18) 0.62511(13) 1.00127(11) 0.0200(3) Uani 1 1 d . . . . .
H14 H 0.075327 0.578025 0.961703 0.024 Uiso 1 1 calc R U . . .
C15 C 0.73845(17) 0.63745(13) 0.86831(11) 0.0197(3) Uani 1 1 d . . . . .
H15A H 0.709365 0.711750 0.852267 0.030 Uiso 1 1 calc R U . . .
H15B H 0.834138 0.621362 0.854236 0.030 Uiso 1 1 calc R U . . .
H15C H 0.749453 0.628254 0.929647 0.030 Uiso 1 1 calc R U . . .
C16 C 0.01750(18) 0.33091(15) 0.72648(12) 0.0264(4) Uani 1 1 d . . . . .
H16A H -0.049664 0.365065 0.757384 0.040 Uiso 1 1 calc R U . . .
H16B H -0.017085 0.257566 0.710673 0.040 Uiso 1 1 calc R U . . .
H16C H 0.017085 0.372309 0.674923 0.040 Uiso 1 1 calc R U . . .
C17 C 0.8168(2) 0.55740(16) 0.48017(11) 0.0281(4) Uani 1 1 d . . . . .
H17A H 0.857634 0.485323 0.476362 0.042 Uiso 1 1 calc R U . . .
H17B H 0.874126 0.609826 0.455696 0.042 Uiso 1 1 calc R U . . .
H17C H 0.711282 0.559245 0.448607 0.042 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 O3 1.5850(11) . ?
V1 O4 1.7824(11) . ?
V1 O1 1.8420(11) . ?
V1 O2 1.9479(11) . ?
V1 N1 2.1299(13) . ?
V1 N3 2.5766(13) 3_667 ?
O1 C2 1.3484(18) . ?
O2 C8 1.3087(17) . ?
O4 C16 1.4214(19) . ?
O5 C5 1.3721(19) . ?
O5 C17 1.422(2) . ?
N1 C7 1.301(2) . ?
N1 N2 1.3938(17) . ?
N2 C8 1.306(2) . ?
N3 C10 1.410(2) . ?
N3 H3B 0.807(19) . ?
N3 H3A 0.82(2) . ?
C1 C6 1.403(2) . ?
C1 C2 1.414(2) . ?
C1 C7 1.461(2) . ?
C2 C3 1.392(2) . ?
C3 C4 1.385(2) . ?
C3 H3 0.9300 . ?
C4 C5 1.397(2) . ?
C4 H4 0.9300 . ?
C5 C6 1.377(2) . ?
C6 H6 0.9300 . ?
C7 C15 1.500(2) . ?
C8 C9 1.476(2) . ?
C9 C14 1.401(2) . ?
C9 C10 1.412(2) . ?
C10 C11 1.395(2) . ?
C11 C12 1.381(2) . ?
C11 H11 0.9300 . ?
C12 C13 1.387(2) . ?
C12 H12 0.9300 . ?
C13 C14 1.382(2) . ?
C13 H13 0.9300 . ?
C14 H14 0.9300 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 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
O3 V1 O4 102.19(6) . . ?
O3 V1 O1 100.94(6) . . ?
O4 V1 O1 102.51(5) . . ?
O3 V1 O2 100.69(6) . . ?
O4 V1 O2 93.06(5) . . ?
O1 V1 O2 149.90(5) . . ?
O3 V1 N1 94.23(5) . . ?
O4 V1 N1 161.09(5) . . ?
O1 V1 N1 83.25(5) . . ?
O2 V1 N1 74.53(5) . . ?
O3 V1 N3 176.29(5) . 3_667 ?
O4 V1 N3 81.50(5) . 3_667 ?
O1 V1 N3 78.41(5) . 3_667 ?
O2 V1 N3 78.64(5) . 3_667 ?
N1 V1 N3 82.08(4) . 3_667 ?
C2 O1 V1 126.58(9) . . ?
C8 O2 V1 118.51(10) . . ?
C16 O4 V1 127.08(10) . . ?
C5 O5 C17 117.03(13) . . ?
C7 N1 N2 116.65(12) . . ?
C7 N1 V1 127.95(10) . . ?
N2 N1 V1 115.32(9) . . ?
C8 N2 N1 109.01(12) . . ?
C10 N3 V1 115.24(10) . 3_667 ?
C10 N3 H3B 112.8(13) . . ?
V1 N3 H3B 97.0(13) 3_667 . ?
C10 N3 H3A 110.2(13) . . ?
V1 N3 H3A 107.5(13) 3_667 . ?
H3B N3 H3A 113.6(18) . . ?
C6 C1 C2 118.32(14) . . ?
C6 C1 C7 119.82(13) . . ?
C2 C1 C7 121.85(14) . . ?
O1 C2 C3 119.13(13) . . ?
O1 C2 C1 121.57(14) . . ?
C3 C2 C1 119.28(14) . . ?
C4 C3 C2 121.35(14) . . ?
C4 C3 H3 119.3 . . ?
C2 C3 H3 119.3 . . ?
C3 C4 C5 119.43(15) . . ?
C3 C4 H4 120.3 . . ?
C5 C4 H4 120.3 . . ?
O5 C5 C6 116.18(14) . . ?
O5 C5 C4 124.07(14) . . ?
C6 C5 C4 119.74(15) . . ?
C5 C6 C1 121.55(14) . . ?
C5 C6 H6 119.2 . . ?
C1 C6 H6 119.2 . . ?
N1 C7 C1 119.23(13) . . ?
N1 C7 C15 121.08(14) . . ?
C1 C7 C15 119.67(14) . . ?
N2 C8 O2 122.43(14) . . ?
N2 C8 C9 120.12(13) . . ?
O2 C8 C9 117.36(13) . . ?
C14 C9 C10 118.77(14) . . ?
C14 C9 C8 117.21(13) . . ?
C10 C9 C8 123.91(14) . . ?
C11 C10 N3 119.02(14) . . ?
C11 C10 C9 118.72(14) . . ?
N3 C10 C9 122.16(14) . . ?
C12 C11 C10 121.29(14) . . ?
C12 C11 H11 119.4 . . ?
C10 C11 H11 119.4 . . ?
C11 C12 C13 120.23(15) . . ?
C11 C12 H12 119.9 . . ?
C13 C12 H12 119.9 . . ?
C14 C13 C12 119.27(16) . . ?
C14 C13 H13 120.4 . . ?
C12 C13 H13 120.4 . . ?
C13 C14 C9 121.50(15) . . ?
C13 C14 H14 119.3 . . ?
C9 C14 H14 119.3 . . ?
C7 C15 H15A 109.5 . . ?
C7 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C7 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
O4 C16 H16A 109.5 . . ?
O4 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
O4 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
O5 C17 H17A 109.5 . . ?
O5 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
O5 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?

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
N3 H3B O4 0.807(19) 2.662(18) 2.9084(17) 99.7(14) 3_667
N3 H3A O2 0.82(2) 2.690(18) 2.9079(17) 97.1(14) 3_667
N3 H3A N2 0.82(2) 2.11(2) 2.7791(19) 138.7(17) .

_refine_diff_density_max         0.373
_refine_diff_density_min         -0.398
_refine_diff_density_rms         0.062

