# Supplementary Information (SI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2026

####################################################################### 
# 
# 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_at4_2024
_database_code_depnum_ccdc_archive 'CCDC 2545749'
loop_
_audit_author_name
_audit_author_address
'Katarzyna Kazimierczuk'
;Gdansk University of Technology, Faculty of Chemistry
Poland
;
_audit_update_record             
;
2026-04-13 deposited with the CCDC.	2026-06-01 downloaded from the CCDC.
;

#------------------ AUDIT DETAILS -------------------------------------------#

_audit_creation_date             2025-06-10
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#
_chemical_name_systematic        
;
 trans-bis(acetylacetonato-k2O,O')oxido(isoquinoline-kN)vanadium(IV)
;
_chemical_formula_moiety         'C19  H21  N  O5  V'
_chemical_formula_sum            'C19 H21 N O5 V'
_chemical_formula_weight         394.31
_chemical_absolute_configuration unk

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'C m'
_symmetry_space_group_name_Hall  'C -2y'
_symmetry_Int_Tables_number      8
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'x, -y, z'
'x+1/2, y+1/2, z'
'x+1/2, -y+1/2, z'

_cell_length_a                   8.7229(6)
_cell_length_b                   13.5442(8)
_cell_length_c                   8.0885(5)
_cell_angle_alpha                90
_cell_angle_beta                 90.419(5)
_cell_angle_gamma                90
_cell_volume                     955.59(10)
_cell_formula_units_Z            2
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    19664
_cell_measurement_theta_min      2.52
_cell_measurement_theta_max      29.53

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#
_exptl_crystal_description       plate
_exptl_crystal_colour            green
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.11
_exptl_crystal_density_diffrn    1.37
_exptl_crystal_F_000             410
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-3 1 0 0.0510
3 -1 0 0.1040
1 0 -3 0.1110
0 0 1 0.0900
0 -1 0 0.0300
-1 -1 -1 0.0860
0 1 0 0.0340

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    0.547
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   
;
        Numerical  absorption  correction was  performed
        after the  optimization of  the  crystal-shape
        description due to Herrendorf?s method
        [Herrendorf, 1994]
        Herrendorf,  W. (1994).HABITUS, a program for the
        optimization  of  the  crystal description for
 the numerical absorption correction by means of
        suitable, psi scanned reflections;dissertation
        1994,Karlsruhe;extension 1998,Gießen
;
_exptl_absorpt_correction_T_min  0.9095
_exptl_absorpt_correction_T_max  0.9650

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#
_diffrn_source                   'GeniX Mo, 0.05 x 0.05 mm2 microfocus'
_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  'parabolic x-ray mirror'
_diffrn_radiation_probe          x-ray
_diffrn_detector                 'image plate (34 cm diameter)'
_diffrn_detector_type            STOE
_diffrn_detector_area_resol_mean 6.67
_diffrn_measurement_device       '2-circle goniometer'
_diffrn_measurement_device_type  'STOE IPDS 2T'
_diffrn_measurement_method       'rotation method'
_diffrn_standards_number         0
_diffrn_reflns_av_R_equivalents  0.0281
_diffrn_reflns_av_unetI/netI     0.0224
_diffrn_reflns_number            7425
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         2.518
_diffrn_reflns_theta_max         29.151
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.959
_diffrn_reflns_point_group_measured_fraction_max 0.945
_reflns_Friedel_fraction_full    0.919
_reflns_Friedel_fraction_max     0.894
_reflns_Friedel_coverage         0.892
_reflns_number_total             2530
_reflns_number_gt                2430
_reflns_threshold_expression     'I > 2σ(I)'

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Ortep for Windows (Farrugia, 2012)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION                                       #
#----------------------------------------------------------------------------#

_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_shelx_SHELXL_version_number     2018/3
_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0722P)²+1.3041P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         2530
_refine_ls_number_parameters     139
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0473
_refine_ls_R_factor_gt           0.0445
_refine_ls_wR_factor_ref         0.1243
_refine_ls_wR_factor_gt          0.1161
_refine_ls_goodness_of_fit_ref   1.083
_refine_ls_restrained_S_all      1.083
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.24(4)
_refine_diff_density_max         0.321
_refine_diff_density_min         -0.709
_refine_diff_density_rms         0.07

#----------------------------------------------------------------------------#
#                   CONSTRAINTS AND RESTRAINTS                               #
#----------------------------------------------------------------------------#


#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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 0 '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 0.006 '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'

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 0.5128(6) 0.2526(4) 0.9262(6) 0.0422(10) Uani 1 1 d . . . . .
H1A H 0.492363 0.186554 0.881731 0.063 Uiso 1 1 calc R U . . .
H1B H 0.415517 0.286694 0.945626 0.063 Uiso 1 1 calc R U . . .
H1C H 0.569706 0.246796 1.030711 0.063 Uiso 1 1 calc R U . . .
C2 C 0.6060(5) 0.3103(3) 0.8048(5) 0.0301(8) Uani 1 1 d . . . . .
C3 C 0.6441(5) 0.2683(3) 0.6528(6) 0.0349(8) Uani 1 1 d . . . . .
H3 H 0.60279 0.205195 0.62721 0.042 Uiso 1 1 calc R U . . .
C4 C 0.7383(5) 0.3127(3) 0.5365(5) 0.0311(8) Uani 1 1 d . . . . .
C5 C 0.7770(6) 0.2595(4) 0.3797(6) 0.0439(10) Uani 1 1 d . . . . .
H5A H 0.875332 0.225431 0.39334 0.066 Uiso 1 1 calc R U . . .
H5B H 0.784267 0.307217 0.288958 0.066 Uiso 1 1 calc R U . . .
H5C H 0.696579 0.211204 0.354263 0.066 Uiso 1 1 calc R U . . .
C6 C 0.3846(7) 0.5 0.6632(7) 0.0321(11) Uani 1 2 d S T P . .
H6 H 0.392184 0.5 0.780425 0.039 Uiso 1 2 calc R U P . .
C7 C 0.2426(6) 0.5 0.5933(7) 0.0304(11) Uani 1 2 d S T P . .
H7 H 0.153991 0.5 0.660862 0.037 Uiso 1 2 calc R U P . .
C8 C 0.2279(7) 0.5 0.4188(7) 0.0269(10) Uani 1 2 d S T P . .
C9 C 0.0841(7) 0.5 0.3354(7) 0.0336(12) Uani 1 2 d S T P . .
H9 H -0.008284 0.5 0.396886 0.04 Uiso 1 2 calc R U P . .
C10 C 0.0788(8) 0.5 0.1670(8) 0.0425(15) Uani 1 2 d S T P . .
H10 H -0.017607 0.5 0.111591 0.051 Uiso 1 2 calc R U P . .
C11 C 0.2144(9) 0.5 0.0745(8) 0.050(2) Uani 1 2 d S T P . .
H11 H 0.207821 0.5 -0.042771 0.06 Uiso 1 2 calc R U P . .
C12 C 0.3565(8) 0.5 0.1494(7) 0.0401(15) Uani 1 2 d S T P . .
H12 H 0.447308 0.5 0.08526 0.048 Uiso 1 2 calc R U P . .
C13 C 0.3645(7) 0.5 0.3243(7) 0.0265(10) Uani 1 2 d S T P . .
C14 C 0.5064(6) 0.5 0.4111(7) 0.0278(10) Uani 1 2 d S T P . .
H14 H 0.598507 0.5 0.34915 0.033 Uiso 1 2 calc R U P . .
N1 N 0.5164(6) 0.5 0.5750(6) 0.0285(9) Uani 1 2 d S T P . .
O1 O 0.9198(5) 0.5 0.8160(5) 0.0318(8) Uani 1 2 d S T P . .
O2 O 0.6451(3) 0.3972(2) 0.8532(3) 0.0291(6) Uani 1 1 d . . . . .
O3 O 0.7984(3) 0.3984(2) 0.5507(4) 0.0295(6) Uani 1 1 d . . . . .
V1 V 0.75633(8) 0.5 0.72339(8) 0.0255(2) Uani 1 2 d S T P . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_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 C2 1.499(6) . ?
C1 H1A 0.98 . ?
C1 H1B 0.98 . ?
C1 H1C 0.98 . ?
C2 O2 1.286(5) . ?
C2 C3 1.397(6) . ?
C3 C4 1.391(6) . ?
C3 H3 0.95 . ?
C4 O3 1.278(5) . ?
C4 C5 1.499(6) . ?
C5 H5A 0.98 . ?
C5 H5B 0.98 . ?
C5 H5C 0.98 . ?
C6 C7 1.358(8) . ?
C6 N1 1.358(8) . ?
C6 H6 0.95 . ?
C7 C8 1.417(7) . ?
C7 H7 0.95 . ?
C8 C13 1.420(8) . ?
C8 C9 1.420(7) . ?
C9 C10 1.362(8) . ?
C9 H9 0.95 . ?
C10 C11 1.404(10) . ?
C10 H10 0.95 . ?
C11 C12 1.376(9) . ?
C11 H11 0.95 . ?
C12 C13 1.416(8) . ?
C12 H12 0.95 . ?
C13 C14 1.419(7) . ?
C14 N1 1.327(7) . ?
C14 H14 0.95 . ?
N1 V1 2.405(5) . ?
O1 V1 1.606(4) . ?
O2 V1 1.999(3) . ?
O3 V1 1.997(3) . ?

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
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
O2 C2 C3 125.2(4) . . ?
O2 C2 C1 115.0(4) . . ?
C3 C2 C1 119.9(4) . . ?
C4 C3 C2 124.4(4) . . ?
C4 C3 H3 117.8 . . ?
C2 C3 H3 117.8 . . ?
O3 C4 C3 125.1(4) . . ?
O3 C4 C5 114.7(4) . . ?
C3 C4 C5 120.2(4) . . ?
C4 C5 H5A 109.5 . . ?
C4 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
C4 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
C7 C6 N1 123.7(5) . . ?
C7 C6 H6 118.2 . . ?
N1 C6 H6 118.2 . . ?
C6 C7 C8 119.4(5) . . ?
C6 C7 H7 120.3 . . ?
C8 C7 H7 120.3 . . ?
C7 C8 C13 117.8(5) . . ?
C7 C8 C9 123.1(5) . . ?
C13 C8 C9 119.1(5) . . ?
C10 C9 C8 119.9(6) . . ?
C10 C9 H9 120.1 . . ?
C8 C9 H9 120.1 . . ?
C9 C10 C11 120.7(6) . . ?
C9 C10 H10 119.7 . . ?
C11 C10 H10 119.7 . . ?
C12 C11 C10 121.7(6) . . ?
C12 C11 H11 119.2 . . ?
C10 C11 H11 119.2 . . ?
C11 C12 C13 118.5(5) . . ?
C11 C12 H12 120.7 . . ?
C13 C12 H12 120.7 . . ?
C12 C13 C14 122.0(5) . . ?
C12 C13 C8 120.2(5) . . ?
C14 C13 C8 117.8(5) . . ?
N1 C14 C13 123.0(5) . . ?
N1 C14 H14 118.5 . . ?
C13 C14 H14 118.5 . . ?
C14 N1 C6 118.4(5) . . ?
C14 N1 V1 123.3(4) . . ?
C6 N1 V1 118.3(4) . . ?
C2 O2 V1 127.4(3) . . ?
C4 O3 V1 127.7(3) . . ?
O1 V1 O3 99.16(15) . 2_565 ?
O1 V1 O3 99.16(15) . . ?
O3 V1 O3 87.15(17) 2_565 . ?
O1 V1 O2 100.81(14) . 2_565 ?
O3 V1 O2 88.83(11) 2_565 2_565 ?
O3 V1 O2 160.01(11) . 2_565 ?
O1 V1 O2 100.81(14) . . ?
O3 V1 O2 160.01(11) 2_565 . ?
O3 V1 O2 88.83(11) . . ?
O2 V1 O2 88.29(17) 2_565 . ?
O1 V1 N1 177.9(2) . . ?
O3 V1 N1 79.31(12) 2_565 . ?
O3 V1 N1 79.31(12) . . ?
O2 V1 N1 80.70(12) 2_565 . ?
O2 V1 N1 80.70(12) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O2 C2 C3 C4 4.3(7) . . . . ?
C1 C2 C3 C4 -175.4(4) . . . . ?
C2 C3 C4 O3 -2.2(7) . . . . ?
C2 C3 C4 C5 177.6(4) . . . . ?
N1 C6 C7 C8 0.0000(10) . . . . ?
C6 C7 C8 C13 0.0000(10) . . . . ?
C6 C7 C8 C9 180.0000(10) . . . . ?
C7 C8 C9 C10 180.0000(10) . . . . ?
C13 C8 C9 C10 0.0000(10) . . . . ?
C8 C9 C10 C11 0.0000(10) . . . . ?
C9 C10 C11 C12 0.0000(10) . . . . ?
C10 C11 C12 C13 0.0000(10) . . . . ?
C11 C12 C13 C14 180 . . . . ?
C11 C12 C13 C8 0.0000(10) . . . . ?
C7 C8 C13 C12 180.0000(10) . . . . ?
C9 C8 C13 C12 0.0000(10) . . . . ?
C7 C8 C13 C14 0.0000(10) . . . . ?
C9 C8 C13 C14 180.0000(10) . . . . ?
C12 C13 C14 N1 180.0000(10) . . . . ?
C8 C13 C14 N1 0.0000(10) . . . . ?
C13 C14 N1 C6 0.0000(10) . . . . ?
C13 C14 N1 V1 180 . . . . ?
C7 C6 N1 C14 0.0000(10) . . . . ?
C7 C6 N1 V1 180.0000(10) . . . . ?
C3 C2 O2 V1 4.7(6) . . . . ?
C1 C2 O2 V1 -175.6(3) . . . . ?
C3 C4 O3 V1 -8.6(6) . . . . ?
C5 C4 O3 V1 171.5(3) . . . . ?


# END of CIF
####################################################################### 
# 
# 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_at6_2024
_database_code_depnum_ccdc_archive 'CCDC 2545748'
loop_
_audit_author_name
_audit_author_address
'Katarzyna Kazimierczuk'
;Gdansk University of Technology, Faculty of Chemistry
Poland
;
_audit_update_record             
;
2026-04-13 deposited with the CCDC.	2026-06-01 downloaded from the CCDC.
;

#------------------ AUDIT DETAILS -------------------------------------------#

_audit_creation_date             2025-06-11
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic



#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#
_chemical_name_systematic        
;
 trans-bis(acetylacetonato-k2O,O')oxido(quinoline-kN)vanadium(IV)
;
_chemical_formula_moiety         'C10 H14 O5 V, C9 H7 N'
_chemical_formula_sum            'C19 H21 N O5 V'
_chemical_formula_weight         394.31
_chemical_absolute_configuration unk

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P n'
_symmetry_space_group_name_Hall  'P -2yac'
_symmetry_Int_Tables_number      7
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'x+1/2, -y, z+1/2'

_cell_length_a                   8.0583(3)
_cell_length_b                   7.7264(4)
_cell_length_c                   15.3312(6)
_cell_angle_alpha                90
_cell_angle_beta                 96.296(3)
_cell_angle_gamma                90
_cell_volume                     948.79(7)
_cell_formula_units_Z            2
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    30748
_cell_measurement_theta_min      2.54
_cell_measurement_theta_max      29.66


#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#
_exptl_crystal_description       plate
_exptl_crystal_colour            green
_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.13
_exptl_crystal_density_diffrn    1.38
_exptl_crystal_F_000             410
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-3 0 -1 0.0670
3 1 2 0.0740
0 0 -1 0.0930
0 0 1 0.0890
1 2 2 0.0460
1 -3 1 0.0710
-1 2 -2 0.0720
#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    0.551
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   
;
        Numerical  absorption  correction was  performed
        after the  optimization of  the  crystal-shape
        description due to Herrendorf?s method
        [Herrendorf, 1994]
        Herrendorf,  W. (1994).HABITUS, a program for the
        optimization  of  the  crystal description for
 the numerical absorption correction by means of
        suitable, psi scanned reflections;dissertation
        1994,Karlsruhe;extension 1998,Gießen
;

_exptl_absorpt_correction_T_min  0.9001
_exptl_absorpt_correction_T_max  0.9502

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#
_diffrn_source                   'GeniX Mo, 0.05 x 0.05 mm2 microfocus'
_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  'parabolic x-ray mirror'
_diffrn_radiation_probe          x-ray
_diffrn_detector                 'image plate (34 cm diameter)'
_diffrn_detector_type            STOE
_diffrn_detector_area_resol_mean 6.67
_diffrn_measurement_device       '2-circle goniometer'
_diffrn_measurement_device_type  'STOE IPDS 2T'
_diffrn_measurement_method       'rotation method'
_diffrn_standards_number         0
_diffrn_reflns_av_R_equivalents  0.0276
_diffrn_reflns_av_unetI/netI     0.0213
_diffrn_reflns_number            14705
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         2.636
_diffrn_reflns_theta_max         29.212
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.965
_diffrn_reflns_point_group_measured_fraction_max 0.95
_reflns_Friedel_fraction_full    0.932
_reflns_Friedel_fraction_max     0.906
_reflns_Friedel_coverage         0.908
_reflns_number_total             4882
_reflns_number_gt                4626
_reflns_threshold_expression     'I > 2σ(I)'

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Ortep for Windows (Farrugia, 2012)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION                                       #
#----------------------------------------------------------------------------#

_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_shelx_SHELXL_version_number     2018/3
_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0699P)²+0.2568P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         4882
_refine_ls_number_parameters     240
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0387
_refine_ls_R_factor_gt           0.0362
_refine_ls_wR_factor_ref         0.1012
_refine_ls_wR_factor_gt          0.0967
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_restrained_S_all      1.052
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.08(2)
_refine_diff_density_max         0.681
_refine_diff_density_min         -0.596
_refine_diff_density_rms         0.06

#----------------------------------------------------------------------------#
#                   CONSTRAINTS AND RESTRAINTS                               #
#----------------------------------------------------------------------------#


#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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 0 '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 0.006 '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'

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 0.9431(5) 0.5552(5) 0.4842(3) 0.0398(7) Uani 1 1 d . . . . .
H1A H 0.994767 0.57881 0.543908 0.06 Uiso 1 1 calc R U . . .
H1B H 0.871725 0.652775 0.463506 0.06 Uiso 1 1 calc R U . . .
H1C H 1.03039 0.53929 0.445199 0.06 Uiso 1 1 calc R U . . .
C2 C 0.8392(4) 0.3933(4) 0.4843(2) 0.0277(6) Uani 1 1 d . . . . .
C3 C 0.8660(4) 0.2776(4) 0.5549(2) 0.0303(6) Uani 1 1 d . . . . .
H3 H 0.951917 0.3036 0.600533 0.036 Uiso 1 1 calc R U . . .
C4 C 0.7738(4) 0.1266(4) 0.56199(18) 0.0267(5) Uani 1 1 d . . . . .
C5 C 0.8154(6) 0.0089(6) 0.6398(3) 0.0393(8) Uani 1 1 d . . . . .
H5A H 0.907662 0.058777 0.678796 0.059 Uiso 1 1 calc R U . . .
H5B H 0.848387 -0.104927 0.619428 0.059 Uiso 1 1 calc R U . . .
H5C H 0.717265 -0.003516 0.671797 0.059 Uiso 1 1 calc R U . . .
C6 C 0.2069(5) 0.5457(5) 0.2570(3) 0.0448(9) Uani 1 1 d . . . . .
H6A H 0.226583 0.532761 0.195413 0.067 Uiso 1 1 calc R U . . .
H6B H 0.268572 0.646453 0.282284 0.067 Uiso 1 1 calc R U . . .
H6C H 0.087306 0.562158 0.260746 0.067 Uiso 1 1 calc R U . . .
C7 C 0.2657(4) 0.3857(5) 0.3072(2) 0.0281(6) Uani 1 1 d . . . . .
C8 C 0.1483(4) 0.2664(4) 0.3329(2) 0.0291(6) Uani 1 1 d . . . . .
H8 H 0.033249 0.28855 0.316168 0.035 Uiso 1 1 calc R U . . .
C9 C 0.1915(3) 0.1175(4) 0.38164(18) 0.0241(5) Uani 1 1 d . . . . .
C10 C 0.0570(5) -0.0073(4) 0.4014(3) 0.0340(5) Uani 1 1 d . . . . .
H10A H -0.052686 0.042061 0.38156 0.051 Uiso 1 1 calc R U . . .
H10B H 0.065328 -0.028354 0.464752 0.051 Uiso 1 1 calc R U . . .
H10C H 0.070925 -0.116709 0.370709 0.051 Uiso 1 1 calc R U . . .
C11 C 0.4580(4) 0.5715(4) 0.4902(2) 0.0297(6) Uani 1 1 d . . . . .
H11 H 0.508958 0.595413 0.43846 0.036 Uiso 1 1 calc R U . . .
C12 C 0.4056(5) 0.7139(4) 0.5378(3) 0.0351(8) Uani 1 1 d . . . . .
H12 H 0.420961 0.829052 0.518463 0.042 Uiso 1 1 calc R U . . .
C13 C 0.3325(5) 0.6824(4) 0.6121(3) 0.0352(7) Uani 1 1 d . . . . .
H13 H 0.295746 0.775895 0.645411 0.042 Uiso 1 1 calc R U . . .
C14 C 0.3115(4) 0.5100(4) 0.6396(2) 0.0262(6) Uani 1 1 d . . . . .
C15 C 0.2383(4) 0.4684(5) 0.7168(2) 0.0332(6) Uani 1 1 d . . . . .
H15 H 0.197135 0.558185 0.750873 0.04 Uiso 1 1 calc R U . . .
C16 C 0.2264(5) 0.3011(5) 0.7425(2) 0.0321(8) Uani 1 1 d . . . . .
H16 H 0.17783 0.274402 0.794622 0.039 Uiso 1 1 calc R U . . .
C17 C 0.2861(4) 0.1668(4) 0.6920(2) 0.0298(6) Uani 1 1 d . . . . .
H17 H 0.278524 0.050299 0.710994 0.036 Uiso 1 1 calc R U . . .
C18 C 0.3545(4) 0.2012(3) 0.6161(2) 0.0260(6) Uani 1 1 d . . . . .
H18 H 0.391708 0.108744 0.582289 0.031 Uiso 1 1 calc R U . . .
C19 C 0.3701(4) 0.3746(3) 0.58774(18) 0.0218(5) Uani 1 1 d . . . . .
N1 N 0.4417(3) 0.4080(3) 0.51192(16) 0.0238(4) Uani 1 1 d . . . . .
O1 O 0.6259(3) 0.0828(3) 0.32462(16) 0.0377(5) Uani 1 1 d . . . . .
O2 O 0.7317(3) 0.3746(3) 0.41808(14) 0.0272(4) Uani 1 1 d . . . . .
O3 O 0.6522(3) 0.0772(3) 0.50712(14) 0.0256(4) Uani 1 1 d . . . . .
O4 O 0.4234(3) 0.3710(3) 0.32367(13) 0.0283(4) Uani 1 1 d . . . . .
O5 O 0.3399(3) 0.0747(3) 0.41185(14) 0.0253(4) Uani 1 1 d . . . . .
V1 V 0.55288(5) 0.19665(5) 0.39847(3) 0.02230(12) Uani 1 1 d . . . . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_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 C2 1.505(5) . ?
C1 H1A 0.98 . ?
C1 H1B 0.98 . ?
C1 H1C 0.98 . ?
C2 O2 1.269(4) . ?
C2 C3 1.402(5) . ?
C3 C4 1.394(4) . ?
C3 H3 0.95 . ?
C4 O3 1.278(4) . ?
C4 C5 1.508(4) . ?
C5 H5A 0.98 . ?
C5 H5B 0.98 . ?
C5 H5C 0.98 . ?
C6 C7 1.505(5) . ?
C6 H6A 0.98 . ?
C6 H6B 0.98 . ?
C6 H6C 0.98 . ?
C7 O4 1.273(4) . ?
C7 C8 1.408(5) . ?
C8 C9 1.395(4) . ?
C8 H8 0.95 . ?
C9 O5 1.277(4) . ?
C9 C10 1.506(4) . ?
C10 H10A 0.98 . ?
C10 H10B 0.98 . ?
C10 H10C 0.98 . ?
C11 N1 1.317(4) . ?
C11 C12 1.411(5) . ?
C11 H11 0.95 . ?
C12 C13 1.361(6) . ?
C12 H12 0.95 . ?
C13 C14 1.413(5) . ?
C13 H13 0.95 . ?
C14 C15 1.416(4) . ?
C14 C19 1.426(4) . ?
C15 C16 1.358(5) . ?
C15 H15 0.95 . ?
C16 C17 1.411(5) . ?
C16 H16 0.95 . ?
C17 C18 1.367(4) . ?
C17 H17 0.95 . ?
C18 C19 1.418(4) . ?
C18 H18 0.95 . ?
C19 N1 1.378(3) . ?
N1 V1 2.615(2) . ?
O1 V1 1.596(2) . ?
O2 V1 1.991(2) . ?
O3 V1 1.994(2) . ?
O4 V1 1.989(2) . ?
O5 V1 1.988(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
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
O2 C2 C3 125.4(3) . . ?
O2 C2 C1 115.1(3) . . ?
C3 C2 C1 119.5(3) . . ?
C4 C3 C2 123.8(3) . . ?
C4 C3 H3 118.1 . . ?
C2 C3 H3 118.1 . . ?
O3 C4 C3 125.2(3) . . ?
O3 C4 C5 115.4(3) . . ?
C3 C4 C5 119.5(3) . . ?
C4 C5 H5A 109.5 . . ?
C4 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
C4 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
C7 C6 H6A 109.5 . . ?
C7 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
C7 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
O4 C7 C8 124.9(3) . . ?
O4 C7 C6 115.2(3) . . ?
C8 C7 C6 119.8(3) . . ?
C9 C8 C7 123.6(3) . . ?
C9 C8 H8 118.2 . . ?
C7 C8 H8 118.2 . . ?
O5 C9 C8 125.2(3) . . ?
O5 C9 C10 115.3(3) . . ?
C8 C9 C10 119.5(3) . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
N1 C11 C12 125.0(3) . . ?
N1 C11 H11 117.5 . . ?
C12 C11 H11 117.5 . . ?
C13 C12 C11 118.4(3) . . ?
C13 C12 H12 120.8 . . ?
C11 C12 H12 120.8 . . ?
C12 C13 C14 119.7(3) . . ?
C12 C13 H13 120.2 . . ?
C14 C13 H13 120.2 . . ?
C13 C14 C15 122.5(3) . . ?
C13 C14 C19 117.9(3) . . ?
C15 C14 C19 119.5(3) . . ?
C16 C15 C14 120.5(3) . . ?
C16 C15 H15 119.7 . . ?
C14 C15 H15 119.7 . . ?
C15 C16 C17 120.1(3) . . ?
C15 C16 H16 119.9 . . ?
C17 C16 H16 119.9 . . ?
C18 C17 C16 121.2(3) . . ?
C18 C17 H17 119.4 . . ?
C16 C17 H17 119.4 . . ?
C17 C18 C19 120.1(3) . . ?
C17 C18 H18 119.9 . . ?
C19 C18 H18 119.9 . . ?
N1 C19 C18 119.7(2) . . ?
N1 C19 C14 121.9(2) . . ?
C18 C19 C14 118.5(3) . . ?
C11 N1 C19 117.1(2) . . ?
C11 N1 V1 112.32(19) . . ?
C19 N1 V1 130.54(17) . . ?
C2 O2 V1 128.2(2) . . ?
C4 O3 V1 128.33(19) . . ?
C7 O4 V1 128.6(2) . . ?
C9 O5 V1 128.63(19) . . ?
O1 V1 O5 101.63(12) . . ?
O1 V1 O4 100.09(12) . . ?
O5 V1 O4 88.63(9) . . ?
O1 V1 O2 99.84(12) . . ?
O5 V1 O2 158.52(9) . . ?
O4 V1 O2 86.83(9) . . ?
O1 V1 O3 101.08(12) . . ?
O5 V1 O3 88.07(9) . . ?
O4 V1 O3 158.81(9) . . ?
O2 V1 O3 88.63(9) . . ?
O1 V1 N1 174.80(12) . . ?
O5 V1 N1 82.22(8) . . ?
O4 V1 N1 76.37(8) . . ?
O2 V1 N1 76.30(8) . . ?
O3 V1 N1 82.45(8) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O2 C2 C3 C4 -1.4(5) . . . . ?
C1 C2 C3 C4 178.5(3) . . . . ?
C2 C3 C4 O3 -1.9(5) . . . . ?
C2 C3 C4 C5 178.7(3) . . . . ?
O4 C7 C8 C9 1.2(5) . . . . ?
C6 C7 C8 C9 -178.1(3) . . . . ?
C7 C8 C9 O5 3.1(5) . . . . ?
C7 C8 C9 C10 -176.5(3) . . . . ?
N1 C11 C12 C13 0.1(6) . . . . ?
C11 C12 C13 C14 0.2(6) . . . . ?
C12 C13 C14 C15 179.2(4) . . . . ?
C12 C13 C14 C19 0.5(5) . . . . ?
C13 C14 C15 C16 -177.5(4) . . . . ?
C19 C14 C15 C16 1.2(5) . . . . ?
C14 C15 C16 C17 -0.5(6) . . . . ?
C15 C16 C17 C18 -0.9(6) . . . . ?
C16 C17 C18 C19 1.4(5) . . . . ?
C17 C18 C19 N1 179.0(3) . . . . ?
C17 C18 C19 C14 -0.6(5) . . . . ?
C13 C14 C19 N1 -1.5(5) . . . . ?
C15 C14 C19 N1 179.7(3) . . . . ?
C13 C14 C19 C18 178.1(3) . . . . ?
C15 C14 C19 C18 -0.7(5) . . . . ?
C12 C11 N1 C19 -1.0(5) . . . . ?
C12 C11 N1 V1 178.5(3) . . . . ?
C18 C19 N1 C11 -177.9(3) . . . . ?
C14 C19 N1 C11 1.7(4) . . . . ?
C18 C19 N1 V1 2.8(4) . . . . ?
C14 C19 N1 V1 -177.7(2) . . . . ?
C3 C2 O2 V1 7.6(5) . . . . ?
C1 C2 O2 V1 -172.2(2) . . . . ?
C3 C4 O3 V1 -1.5(4) . . . . ?
C5 C4 O3 V1 178.0(2) . . . . ?
C8 C7 O4 V1 -6.8(5) . . . . ?
C6 C7 O4 V1 172.6(3) . . . . ?
C8 C9 O5 V1 -1.5(4) . . . . ?
C10 C9 O5 V1 178.1(2) . . . . ?

# END of CIF

####################################################################### 
# 
# 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_wd7
_database_code_depnum_ccdc_archive 'CCDC 2545750'
loop_
_audit_author_name
_audit_author_address
'Katarzyna Kazimierczuk'
;Gdansk University of Technology, Faculty of Chemistry
Poland
;
_audit_update_record             
;
2026-04-13 deposited with the CCDC.	2026-06-01 downloaded from the CCDC.
;

#------------------ AUDIT DETAILS -------------------------------------------#

_audit_creation_date             2025-06-13
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic


#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#
_chemical_name_systematic        
;
 cis-bis(acetylacetonato-k2O,O')oxido(isoquinoline-kN)vanadium(IV)
;
_chemical_formula_moiety         'C19  H21  N  O5  V'
_chemical_formula_sum            'C19 H21 N O5 V'
_chemical_formula_weight         394.31
_chemical_absolute_configuration unk

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/c'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_Int_Tables_number      14
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   8.222(2)
_cell_length_b                   20.454(8)
_cell_length_c                   11.506(4)
_cell_angle_alpha                90
_cell_angle_beta                 108.51(2)
_cell_angle_gamma                90
_cell_volume                     1834.8(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    5317
_cell_measurement_theta_min      2.05
_cell_measurement_theta_max      25.78

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#
_exptl_crystal_description       needle
_exptl_crystal_colour            green
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.05
_exptl_crystal_density_diffrn    1.427
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             820

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    0.57
_exptl_absorpt_correction_type   none

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#
_diffrn_source                   'GeniX Mo, 0.05 x 0.05 mm2 microfocus'
_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  'parabolic x-ray mirror'
_diffrn_radiation_probe          x-ray
_diffrn_detector                 'image plate (34 cm diameter)'
_diffrn_detector_type            STOE
_diffrn_detector_area_resol_mean 6.67
_diffrn_measurement_device       '2-circle goniometer'
_diffrn_measurement_device_type  'STOE IPDS 2T'
_diffrn_measurement_method       'rotation method'
_diffrn_standards_number         0
_diffrn_reflns_av_R_equivalents  0.0597
_diffrn_reflns_av_unetI/netI     0.0395
_diffrn_reflns_number            27562
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.613
_diffrn_reflns_theta_max         29.295
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.986
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.986
_reflns_Friedel_coverage         0
_reflns_number_total             4955
_reflns_number_gt                3629
_reflns_threshold_expression     'I > 2σ(I)'

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Ortep for Windows (Farrugia, 2012)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION                                       #
#----------------------------------------------------------------------------#

_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_shelx_SHELXL_version_number     2018/3
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0669P)²+0.4880P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         4955
_refine_ls_number_parameters     239
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0685
_refine_ls_R_factor_gt           0.0445
_refine_ls_wR_factor_ref         0.1175
_refine_ls_wR_factor_gt          0.108
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_restrained_S_all      1.029
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.484
_refine_diff_density_min         -0.389
_refine_diff_density_rms         0.079

#----------------------------------------------------------------------------#
#                   CONSTRAINTS AND RESTRAINTS                               #
#----------------------------------------------------------------------------#


#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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 0 '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 0.006 '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'

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 0.9473(3) 0.23198(11) 0.6874(2) 0.0356(5) Uani 1 1 d . . . . .
H1A H 1.063729 0.226009 0.744141 0.053 Uiso 1 1 calc R U . . .
H1B H 0.936823 0.209679 0.609955 0.053 Uiso 1 1 calc R U . . .
H1C H 0.864366 0.213509 0.723478 0.053 Uiso 1 1 calc R U . . .
C2 C 0.9123(2) 0.30350(10) 0.66380(19) 0.0232(4) Uani 1 1 d . . . . .
C3 C 0.9005(3) 0.32956(10) 0.54964(19) 0.0262(4) Uani 1 1 d . . . . .
H3 H 0.908556 0.300066 0.487929 0.031 Uiso 1 1 calc R U . . .
C4 C 0.8777(2) 0.39550(10) 0.51895(18) 0.0225(4) Uani 1 1 d . . . . .
C5 C 0.8788(3) 0.41832(11) 0.39517(19) 0.0297(5) Uani 1 1 d . . . . .
H5A H 0.763507 0.432906 0.347155 0.045 Uiso 1 1 calc R U . . .
H5B H 0.914 0.382233 0.352449 0.045 Uiso 1 1 calc R U . . .
H5C H 0.959642 0.454703 0.405127 0.045 Uiso 1 1 calc R U . . .
C6 C 0.6814(3) 0.41867(11) 1.07659(18) 0.0281(5) Uani 1 1 d . . . . .
H6A H 0.670915 0.373598 1.102204 0.042 Uiso 1 1 calc R U . . .
H6B H 0.589434 0.44534 1.089328 0.042 Uiso 1 1 calc R U . . .
H6C H 0.792826 0.43649 1.125246 0.042 Uiso 1 1 calc R U . . .
C7 C 0.6674(3) 0.41959(9) 0.94362(18) 0.0215(4) Uani 1 1 d . . . . .
C8 C 0.5063(3) 0.42091(10) 0.85554(19) 0.0249(4) Uani 1 1 d . . . . .
H8 H 0.40932 0.426347 0.882618 0.03 Uiso 1 1 calc R U . . .
C9 C 0.4777(2) 0.41473(10) 0.72958(18) 0.0213(4) Uani 1 1 d . . . . .
C10 C 0.2962(3) 0.40985(12) 0.6462(2) 0.0310(5) Uani 1 1 d . . . . .
H10A H 0.273196 0.445324 0.585836 0.046 Uiso 1 1 calc R U . . .
H10B H 0.217611 0.413384 0.694486 0.046 Uiso 1 1 calc R U . . .
H10C H 0.279254 0.367665 0.60361 0.046 Uiso 1 1 calc R U . . .
C11 C 0.6483(3) 0.55288(10) 0.64791(17) 0.0232(4) Uani 1 1 d . . . . .
H11 H 0.626064 0.52641 0.57672 0.028 Uiso 1 1 calc R U . . .
C12 C 0.5677(3) 0.61150(10) 0.63781(18) 0.0256(4) Uani 1 1 d . . . . .
H12 H 0.493435 0.625769 0.560626 0.031 Uiso 1 1 calc R U . . .
C13 C 0.5950(2) 0.65119(10) 0.74282(18) 0.0232(4) Uani 1 1 d . . . . .
C14 C 0.5090(3) 0.71122(11) 0.7434(2) 0.0284(4) Uani 1 1 d . . . . .
H14 H 0.429452 0.72729 0.669666 0.034 Uiso 1 1 calc R U . . .
C15 C 0.5402(3) 0.74598(11) 0.8495(2) 0.0317(5) Uani 1 1 d . . . . .
H15 H 0.480305 0.78571 0.849337 0.038 Uiso 1 1 calc R U . . .
C16 C 0.6601(3) 0.72371(11) 0.9593(2) 0.0304(5) Uani 1 1 d . . . . .
H16 H 0.681372 0.748918 1.031931 0.036 Uiso 1 1 calc R U . . .
C17 C 0.7465(3) 0.66608(10) 0.96247(19) 0.0262(4) Uani 1 1 d . . . . .
H17 H 0.827768 0.651485 1.036699 0.031 Uiso 1 1 calc R U . . .
C18 C 0.7135(2) 0.62852(10) 0.85409(18) 0.0214(4) Uani 1 1 d . . . . .
C19 C 0.7932(2) 0.56719(9) 0.85429(17) 0.0210(4) Uani 1 1 d . . . . .
H19 H 0.873772 0.552161 0.928442 0.025 Uiso 1 1 calc R U . . .
N1 N 0.76026(19) 0.52993(8) 0.75563(14) 0.0203(3) Uani 1 1 d . . . . .
O1 O 1.05586(17) 0.45482(7) 0.83006(13) 0.0248(3) Uani 1 1 d . . . . .
O2 O 0.89891(18) 0.33600(7) 0.75468(13) 0.0251(3) Uani 1 1 d . . . . .
O3 O 0.85566(17) 0.44018(7) 0.58995(12) 0.0215(3) Uani 1 1 d . . . . .
O4 O 0.59598(17) 0.41133(7) 0.68034(12) 0.0214(3) Uani 1 1 d . . . . .
O5 O 0.80979(17) 0.41789(7) 0.92026(12) 0.0219(3) Uani 1 1 d . . . . .
V1 V 0.86194(4) 0.43225(2) 0.76456(3) 0.01865(10) Uani 1 1 d . . . . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_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 C2 1.499(3) . ?
C1 H1A 0.98 . ?
C1 H1B 0.98 . ?
C1 H1C 0.98 . ?
C2 O2 1.273(2) . ?
C2 C3 1.392(3) . ?
C3 C4 1.392(3) . ?
C3 H3 0.95 . ?
C4 O3 1.276(2) . ?
C4 C5 1.501(3) . ?
C5 H5A 0.98 . ?
C5 H5B 0.98 . ?
C5 H5C 0.98 . ?
C6 C7 1.498(3) . ?
C6 H6A 0.98 . ?
C6 H6B 0.98 . ?
C6 H6C 0.98 . ?
C7 O5 1.282(2) . ?
C7 C8 1.389(3) . ?
C8 C9 1.398(3) . ?
C8 H8 0.95 . ?
C9 O4 1.273(2) . ?
C9 C10 1.499(3) . ?
C10 H10A 0.98 . ?
C10 H10B 0.98 . ?
C10 H10C 0.98 . ?
C11 C12 1.357(3) . ?
C11 N1 1.371(2) . ?
C11 H11 0.95 . ?
C12 C13 1.413(3) . ?
C12 H12 0.95 . ?
C13 C14 1.418(3) . ?
C13 C18 1.418(3) . ?
C14 C15 1.365(3) . ?
C14 H14 0.95 . ?
C15 C16 1.408(3) . ?
C15 H15 0.95 . ?
C16 C17 1.371(3) . ?
C16 H16 0.95 . ?
C17 C18 1.416(3) . ?
C17 H17 0.95 . ?
C18 C19 1.415(3) . ?
C19 N1 1.322(2) . ?
C19 H19 0.95 . ?
N1 V1 2.1558(18) . ?
O1 V1 1.6001(15) . ?
O2 V1 2.0007(16) . ?
O3 V1 1.9998(15) . ?
O4 V1 2.1350(15) . ?
O5 V1 1.9916(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
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
O2 C2 C3 125.22(19) . . ?
O2 C2 C1 115.01(19) . . ?
C3 C2 C1 119.76(19) . . ?
C4 C3 C2 125.03(19) . . ?
C4 C3 H3 117.5 . . ?
C2 C3 H3 117.5 . . ?
O3 C4 C3 124.51(19) . . ?
O3 C4 C5 115.42(18) . . ?
C3 C4 C5 120.07(18) . . ?
C4 C5 H5A 109.5 . . ?
C4 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
C4 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
C7 C6 H6A 109.5 . . ?
C7 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
C7 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
O5 C7 C8 124.77(18) . . ?
O5 C7 C6 115.79(18) . . ?
C8 C7 C6 119.43(18) . . ?
C7 C8 C9 124.17(19) . . ?
C7 C8 H8 117.9 . . ?
C9 C8 H8 117.9 . . ?
O4 C9 C8 124.43(18) . . ?
O4 C9 C10 117.18(18) . . ?
C8 C9 C10 118.37(18) . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C12 C11 N1 123.33(18) . . ?
C12 C11 H11 118.3 . . ?
N1 C11 H11 118.3 . . ?
C11 C12 C13 119.59(18) . . ?
C11 C12 H12 120.2 . . ?
C13 C12 H12 120.2 . . ?
C12 C13 C14 123.86(19) . . ?
C12 C13 C18 117.45(19) . . ?
C14 C13 C18 118.67(19) . . ?
C15 C14 C13 120.2(2) . . ?
C15 C14 H14 119.9 . . ?
C13 C14 H14 119.9 . . ?
C14 C15 C16 120.9(2) . . ?
C14 C15 H15 119.6 . . ?
C16 C15 H15 119.6 . . ?
C17 C16 C15 120.8(2) . . ?
C17 C16 H16 119.6 . . ?
C15 C16 H16 119.6 . . ?
C16 C17 C18 119.4(2) . . ?
C16 C17 H17 120.3 . . ?
C18 C17 H17 120.3 . . ?
C19 C18 C17 121.36(18) . . ?
C19 C18 C13 118.45(18) . . ?
C17 C18 C13 120.17(19) . . ?
N1 C19 C18 122.77(18) . . ?
N1 C19 H19 118.6 . . ?
C18 C19 H19 118.6 . . ?
C19 N1 C11 118.33(17) . . ?
C19 N1 V1 121.52(13) . . ?
C11 N1 V1 119.96(13) . . ?
C2 O2 V1 127.95(13) . . ?
C4 O3 V1 128.40(13) . . ?
C9 O4 V1 127.15(13) . . ?
C7 O5 V1 131.01(13) . . ?
O1 V1 O5 94.92(7) . . ?
O1 V1 O3 98.85(7) . . ?
O5 V1 O3 166.23(6) . . ?
O1 V1 O2 99.45(7) . . ?
O5 V1 O2 89.20(6) . . ?
O3 V1 O2 88.78(6) . . ?
O1 V1 O4 174.52(7) . . ?
O5 V1 O4 84.08(6) . . ?
O3 V1 O4 82.19(6) . . ?
O2 V1 O4 85.94(6) . . ?
O1 V1 N1 93.92(7) . . ?
O5 V1 N1 89.35(6) . . ?
O3 V1 N1 89.48(6) . . ?
O2 V1 N1 166.63(6) . . ?
O4 V1 N1 80.69(6) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O2 C2 C3 C4 2.2(3) . . . . ?
C1 C2 C3 C4 -176.4(2) . . . . ?
C2 C3 C4 O3 -3.9(3) . . . . ?
C2 C3 C4 C5 175.84(19) . . . . ?
O5 C7 C8 C9 5.9(3) . . . . ?
C6 C7 C8 C9 -172.78(19) . . . . ?
C7 C8 C9 O4 -4.6(3) . . . . ?
C7 C8 C9 C10 173.6(2) . . . . ?
N1 C11 C12 C13 -1.6(3) . . . . ?
C11 C12 C13 C14 -176.0(2) . . . . ?
C11 C12 C13 C18 2.9(3) . . . . ?
C12 C13 C14 C15 178.6(2) . . . . ?
C18 C13 C14 C15 -0.2(3) . . . . ?
C13 C14 C15 C16 1.3(3) . . . . ?
C14 C15 C16 C17 -1.0(3) . . . . ?
C15 C16 C17 C18 -0.4(3) . . . . ?
C16 C17 C18 C19 -176.84(19) . . . . ?
C16 C17 C18 C13 1.4(3) . . . . ?
C12 C13 C18 C19 -1.7(3) . . . . ?
C14 C13 C18 C19 177.21(18) . . . . ?
C12 C13 C18 C17 179.94(18) . . . . ?
C14 C13 C18 C17 -1.1(3) . . . . ?
C17 C18 C19 N1 177.48(18) . . . . ?
C13 C18 C19 N1 -0.8(3) . . . . ?
C18 C19 N1 C11 2.2(3) . . . . ?
C18 C19 N1 V1 -172.85(14) . . . . ?
C12 C11 N1 C19 -1.0(3) . . . . ?
C12 C11 N1 V1 174.15(16) . . . . ?
C3 C2 O2 V1 -1.2(3) . . . . ?
C1 C2 O2 V1 177.43(14) . . . . ?
C3 C4 O3 V1 4.4(3) . . . . ?
C5 C4 O3 V1 -175.33(13) . . . . ?
C8 C9 O4 V1 -12.9(3) . . . . ?
C10 C9 O4 V1 168.86(14) . . . . ?
C8 C7 O5 V1 12.4(3) . . . . ?
C6 C7 O5 V1 -168.89(13) . . . . ?

# END of CIF

