# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2021

####################################################################### 
# 
# 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_2
_database_code_depnum_ccdc_archive 'CCDC 1997038'
loop_
_audit_author_name
_audit_author_address
'Marta S. Krawczyk '
;Faculty of Pharmacy, Wroclaw Medical University
Poland
;
_audit_update_record             
;
2020-04-15 deposited with the CCDC.	2021-03-05 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C25 H33 N2 O4 V'
_chemical_formula_sum            'C25 H33 N2 O4 V'
_chemical_formula_weight         476.47

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                   12.011(3)
_cell_length_b                   14.728(3)
_cell_length_c                   13.307(3)
_cell_angle_alpha                90
_cell_angle_beta                 97.28(2)
_cell_angle_gamma                90
_cell_volume                     2335.0(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    5660
_cell_measurement_theta_min      2.8
_cell_measurement_theta_max      31

_exptl_crystal_description       plate
_exptl_crystal_colour            red
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.355
_exptl_crystal_F_000             1008
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.490
_exptl_crystal_size_mid          0.230
_exptl_crystal_size_min          0.060
_exptl_absorpt_coefficient_mu    0.459
_shelx_estimated_absorpt_T_min   0.806
_shelx_estimated_absorpt_T_max   0.973
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_correction_T_min  0.864
_exptl_absorpt_correction_T_max  0.974
_exptl_absorpt_process_details   
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.33.66 (release 28-04-2010 CrysAlis171 .NET)
(compiled Apr 28 2010,14:27:37)
Analytical numeric absorption correction using a multifaceted crystal
                        model based on expressions derived by R.C. Clark & J.S.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
;
_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_measurement_device_type  'Xcalibur, ccd camera Ruby'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            15428
_diffrn_reflns_av_unetI/netI     0.0431
_diffrn_reflns_av_R_equivalents  0.0275
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.808
_diffrn_reflns_theta_max         30.836
_diffrn_reflns_theta_full        25.500
_diffrn_measured_fraction_theta_max 0.908
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.908
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.908
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             6668
_reflns_number_gt                5381
_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 CCD; Oxford-Diffraction Poland, 2003'
_computing_cell_refinement       'CrysAlis RED; Oxford-Diffraction Poland, 2003'
_computing_data_reduction        'CrysAlis RED; Oxford-Diffraction Poland, 2003'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_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)+(0.0368P)²+1.1104P]
 where P=(Fo²+2Fc²)/3
;
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         6668
_refine_ls_number_parameters     295
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0548
_refine_ls_R_factor_gt           0.0394
_refine_ls_wR_factor_ref         0.0939
_refine_ls_wR_factor_gt          0.0871
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_restrained_S_all      1.021
_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
V V 0.67378(2) 0.33409(2) 0.57704(2) 0.01191(7) Uani 1 1 d . . . . .
O1 O 0.79538(9) 0.34904(7) 0.68554(8) 0.0156(2) Uani 1 1 d . . . . .
O2 O 0.53936(9) 0.32741(7) 0.48157(8) 0.0145(2) Uani 1 1 d . . . . .
C1 C 0.81351(13) 0.43216(10) 0.72651(11) 0.0148(3) Uani 1 1 d . . . . .
C2 C 0.91405(13) 0.47902(11) 0.72398(12) 0.0183(3) Uani 1 1 d . . . . .
H2 H 0.9729 0.4521 0.6928 0.022 Uiso 1 1 calc R U . . .
C3 C 0.92859(14) 0.56510(11) 0.76695(12) 0.0198(3) Uani 1 1 d . . . . .
H3 H 0.9978 0.5958 0.7649 0.024 Uiso 1 1 calc R U . . .
C4 C 0.84464(14) 0.60732(11) 0.81273(12) 0.0190(3) Uani 1 1 d . . . . .
C5 C 0.74438(13) 0.55947(11) 0.81548(11) 0.0172(3) Uani 1 1 d . . . . .
H5 H 0.6854 0.5871 0.8458 0.021 Uiso 1 1 calc R U . . .
C6 C 0.72869(13) 0.47277(10) 0.77511(11) 0.0155(3) Uani 1 1 d . . . . .
C7 C 0.62654(13) 0.41583(11) 0.78512(11) 0.0154(3) Uani 1 1 d . . . . .
H7A H 0.6500 0.3601 0.8237 0.019 Uiso 1 1 calc R U . . .
H7B H 0.5757 0.4502 0.8242 0.019 Uiso 1 1 calc R U . . .
N1 N 0.56373(10) 0.38960(8) 0.68480(9) 0.0132(2) Uani 1 1 d . . . . .
C8 C 0.49839(13) 0.46908(10) 0.64246(12) 0.0166(3) Uani 1 1 d . . . . .
H8A H 0.5495 0.5198 0.6350 0.025 Uiso 1 1 calc R U . . .
H8B H 0.4444 0.4867 0.6883 0.025 Uiso 1 1 calc R U . . .
H8C H 0.4581 0.4533 0.5761 0.025 Uiso 1 1 calc R U . . .
C9 C 0.48502(13) 0.31361(10) 0.69903(11) 0.0154(3) Uani 1 1 d . . . . .
H9A H 0.4287 0.3087 0.6382 0.019 Uiso 1 1 calc R U . . .
H9B H 0.4447 0.3272 0.7577 0.019 Uiso 1 1 calc R U . . .
C10 C 0.54632(14) 0.22353(11) 0.71677(12) 0.0179(3) Uani 1 1 d . . . . .
H10A H 0.5888 0.2235 0.7856 0.021 Uiso 1 1 calc R U . . .
H10B H 0.4904 0.1739 0.7137 0.021 Uiso 1 1 calc R U . . .
N2 N 0.62586(11) 0.20530(9) 0.64085(9) 0.0149(3) Uani 1 1 d . . . . .
C11 C 0.72627(14) 0.15778(11) 0.69241(13) 0.0209(3) Uani 1 1 d . . . . .
H11A H 0.7782 0.1446 0.6432 0.031 Uiso 1 1 calc R U . . .
H11B H 0.7032 0.1008 0.7218 0.031 Uiso 1 1 calc R U . . .
H11C H 0.7636 0.1966 0.7463 0.031 Uiso 1 1 calc R U . . .
C12 C 0.57674(13) 0.14425(10) 0.55701(11) 0.0158(3) Uani 1 1 d . . . . .
H12A H 0.5629 0.0842 0.5864 0.019 Uiso 1 1 calc R U . . .
H12B H 0.6333 0.1356 0.5098 0.019 Uiso 1 1 calc R U . . .
C13 C 0.45776(12) 0.26604(10) 0.46118(11) 0.0138(3) Uani 1 1 d . . . . .
C14 C 0.35517(13) 0.29153(11) 0.40565(11) 0.0159(3) Uani 1 1 d . . . . .
H14 H 0.3449 0.3523 0.3824 0.019 Uiso 1 1 calc R U . . .
C15 C 0.26870(13) 0.22947(11) 0.38426(12) 0.0180(3) Uani 1 1 d . . . . .
H15 H 0.2000 0.2488 0.3471 0.022 Uiso 1 1 calc R U . . .
C16 C 0.28005(14) 0.13943(11) 0.41604(12) 0.0187(3) Uani 1 1 d . . . . .
C17 C 0.38148(13) 0.11503(10) 0.47266(12) 0.0173(3) Uani 1 1 d . . . . .
H17 H 0.3910 0.0542 0.4958 0.021 Uiso 1 1 calc R U . . .
C18 C 0.46916(13) 0.17607(10) 0.49663(11) 0.0145(3) Uani 1 1 d . . . . .
C19 C 0.85969(16) 0.70073(12) 0.85949(13) 0.0254(4) Uani 1 1 d . . . . .
H19A H 0.7983 0.7403 0.8304 0.038 Uiso 1 1 calc R U . . .
H19B H 0.9315 0.7262 0.8455 0.038 Uiso 1 1 calc R U . . .
H19C H 0.8590 0.6962 0.9329 0.038 Uiso 1 1 calc R U . . .
C20 C 0.18543(15) 0.07202(12) 0.39289(15) 0.0281(4) Uani 1 1 d . . . . .
H20A H 0.1941 0.0398 0.3299 0.042 Uiso 1 1 calc R U . . .
H20B H 0.1135 0.1043 0.3852 0.042 Uiso 1 1 calc R U . . .
H20C H 0.1873 0.0283 0.4486 0.042 Uiso 1 1 calc R U . . .
O3 O 0.71281(9) 0.45260(7) 0.51572(8) 0.0143(2) Uani 1 1 d . . . . .
O4 O 0.77262(9) 0.26941(7) 0.49233(8) 0.0167(2) Uani 1 1 d . . . . .
C21 C 0.79897(13) 0.46681(10) 0.47093(11) 0.0148(3) Uani 1 1 d . . . . .
C22 C 0.87142(13) 0.39870(11) 0.44390(12) 0.0170(3) Uani 1 1 d . . . . .
H22 H 0.9375 0.4176 0.4174 0.020 Uiso 1 1 calc R U . . .
C23 C 0.85425(13) 0.30575(11) 0.45285(11) 0.0156(3) Uani 1 1 d . . . . .
C24 C 0.93213(14) 0.23962(12) 0.41101(13) 0.0212(3) Uani 1 1 d . . . . .
H24A H 0.9485 0.1893 0.4587 0.032 Uiso 1 1 calc R U . . .
H24B H 1.0022 0.2705 0.4011 0.032 Uiso 1 1 calc R U . . .
H24C H 0.8964 0.2160 0.3460 0.032 Uiso 1 1 calc R U . . .
C25 C 0.82008(14) 0.56397(11) 0.44440(13) 0.0226(3) Uani 1 1 d . . . . .
H25A H 0.7690 0.5813 0.3841 0.034 Uiso 1 1 calc R U . . .
H25B H 0.8979 0.5707 0.4306 0.034 Uiso 1 1 calc R U . . .
H25C H 0.8072 0.6033 0.5012 0.034 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
V O2 1.9263(12) . ?
V O1 1.9317(12) . ?
V O4 1.9817(11) . ?
V O3 2.0072(11) . ?
V N2 2.1850(13) . ?
V N1 2.2253(13) . ?
O1 C1 1.3466(18) . ?
O2 C13 1.3357(18) . ?
C1 C2 1.395(2) . ?
C1 C6 1.407(2) . ?
C2 C3 1.393(2) . ?
C2 H2 0.9500 . ?
C3 C4 1.389(2) . ?
C3 H3 0.9500 . ?
C4 C5 1.400(2) . ?
C4 C19 1.511(2) . ?
C5 C6 1.389(2) . ?
C5 H5 0.9500 . ?
C6 C7 1.506(2) . ?
C7 N1 1.4985(19) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
N1 C8 1.4804(19) . ?
N1 C9 1.4924(19) . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C9 C10 1.521(2) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 N2 1.500(2) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
N2 C11 1.485(2) . ?
N2 C12 1.4948(19) . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 C18 1.507(2) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 C14 1.405(2) . ?
C13 C18 1.407(2) . ?
C14 C15 1.386(2) . ?
C14 H14 0.9500 . ?
C15 C16 1.393(2) . ?
C15 H15 0.9500 . ?
C16 C17 1.396(2) . ?
C16 C20 1.511(2) . ?
C17 C18 1.391(2) . ?
C17 H17 0.9500 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
O3 C21 1.2754(18) . ?
O4 C23 1.2862(19) . ?
C21 C22 1.404(2) . ?
C21 C25 1.503(2) . ?
C22 C23 1.392(2) . ?
C22 H22 0.9500 . ?
C23 C24 1.505(2) . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 0.9800 . ?
C25 H25A 0.9800 . ?
C25 H25B 0.9800 . ?
C25 H25C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O2 V O1 171.85(5) . . ?
O2 V O4 96.47(5) . . ?
O1 V O4 91.67(5) . . ?
O2 V O3 89.75(4) . . ?
O1 V O3 90.65(5) . . ?
O4 V O3 89.95(5) . . ?
O2 V N2 88.39(5) . . ?
O1 V N2 91.14(5) . . ?
O4 V N2 90.57(5) . . ?
O3 V N2 178.12(5) . . ?
O2 V N1 85.82(5) . . ?
O1 V N1 86.05(5) . . ?
O4 V N1 172.20(5) . . ?
O3 V N1 97.52(5) . . ?
N2 V N1 82.03(5) . . ?
C1 O1 V 118.32(9) . . ?
C13 O2 V 134.49(9) . . ?
O1 C1 C2 122.41(14) . . ?
O1 C1 C6 118.89(14) . . ?
C2 C1 C6 118.69(14) . . ?
C3 C2 C1 120.29(15) . . ?
C3 C2 H2 119.9 . . ?
C1 C2 H2 119.9 . . ?
C4 C3 C2 121.82(15) . . ?
C4 C3 H3 119.1 . . ?
C2 C3 H3 119.1 . . ?
C3 C4 C5 117.43(15) . . ?
C3 C4 C19 122.17(15) . . ?
C5 C4 C19 120.40(15) . . ?
C6 C5 C4 121.86(15) . . ?
C6 C5 H5 119.1 . . ?
C4 C5 H5 119.1 . . ?
C5 C6 C1 119.85(14) . . ?
C5 C6 C7 123.37(14) . . ?
C1 C6 C7 116.70(13) . . ?
N1 C7 C6 112.87(12) . . ?
N1 C7 H7A 109.0 . . ?
C6 C7 H7A 109.0 . . ?
N1 C7 H7B 109.0 . . ?
C6 C7 H7B 109.0 . . ?
H7A C7 H7B 107.8 . . ?
C8 N1 C9 109.11(12) . . ?
C8 N1 C7 108.54(12) . . ?
C9 N1 C7 109.62(11) . . ?
C8 N1 V 112.01(9) . . ?
C9 N1 V 104.11(9) . . ?
C7 N1 V 113.31(9) . . ?
N1 C8 H8A 109.5 . . ?
N1 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
N1 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
N1 C9 C10 111.83(12) . . ?
N1 C9 H9A 109.3 . . ?
C10 C9 H9A 109.3 . . ?
N1 C9 H9B 109.3 . . ?
C10 C9 H9B 109.3 . . ?
H9A C9 H9B 107.9 . . ?
N2 C10 C9 112.87(12) . . ?
N2 C10 H10A 109.0 . . ?
C9 C10 H10A 109.0 . . ?
N2 C10 H10B 109.0 . . ?
C9 C10 H10B 109.0 . . ?
H10A C10 H10B 107.8 . . ?
C11 N2 C12 106.38(12) . . ?
C11 N2 C10 108.81(12) . . ?
C12 N2 C10 112.68(12) . . ?
C11 N2 V 110.50(10) . . ?
C12 N2 V 109.31(9) . . ?
C10 N2 V 109.15(9) . . ?
N2 C11 H11A 109.5 . . ?
N2 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
N2 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
N2 C12 C18 116.20(12) . . ?
N2 C12 H12A 108.2 . . ?
C18 C12 H12A 108.2 . . ?
N2 C12 H12B 108.2 . . ?
C18 C12 H12B 108.2 . . ?
H12A C12 H12B 107.4 . . ?
O2 C13 C14 119.87(13) . . ?
O2 C13 C18 122.09(14) . . ?
C14 C13 C18 118.00(14) . . ?
C15 C14 C13 121.08(14) . . ?
C15 C14 H14 119.5 . . ?
C13 C14 H14 119.5 . . ?
C14 C15 C16 121.57(15) . . ?
C14 C15 H15 119.2 . . ?
C16 C15 H15 119.2 . . ?
C15 C16 C17 117.00(14) . . ?
C15 C16 C20 121.42(15) . . ?
C17 C16 C20 121.56(15) . . ?
C18 C17 C16 122.77(15) . . ?
C18 C17 H17 118.6 . . ?
C16 C17 H17 118.6 . . ?
C17 C18 C13 119.54(14) . . ?
C17 C18 C12 119.63(14) . . ?
C13 C18 C12 120.79(13) . . ?
C4 C19 H19A 109.5 . . ?
C4 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C4 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C16 C20 H20A 109.5 . . ?
C16 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C16 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C21 O3 V 125.30(10) . . ?
C23 O4 V 125.10(10) . . ?
O3 C21 C22 124.64(14) . . ?
O3 C21 C25 115.91(14) . . ?
C22 C21 C25 119.44(14) . . ?
C23 C22 C21 125.27(14) . . ?
C23 C22 H22 117.4 . . ?
C21 C22 H22 117.4 . . ?
O4 C23 C22 124.97(14) . . ?
O4 C23 C24 115.06(14) . . ?
C22 C23 C24 119.94(14) . . ?
C23 C24 H24A 109.5 . . ?
C23 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
C23 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C21 C25 H25A 109.5 . . ?
C21 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
C21 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?

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
V O1 C1 C2 -118.88(14) . . . . ?
V O1 C1 C6 62.15(16) . . . . ?
O1 C1 C2 C3 179.65(14) . . . . ?
C6 C1 C2 C3 -1.4(2) . . . . ?
C1 C2 C3 C4 -0.4(2) . . . . ?
C2 C3 C4 C5 0.8(2) . . . . ?
C2 C3 C4 C19 -179.97(15) . . . . ?
C3 C4 C5 C6 0.6(2) . . . . ?
C19 C4 C5 C6 -178.64(15) . . . . ?
C4 C5 C6 C1 -2.4(2) . . . . ?
C4 C5 C6 C7 174.14(14) . . . . ?
O1 C1 C6 C5 -178.25(13) . . . . ?
C2 C1 C6 C5 2.7(2) . . . . ?
O1 C1 C6 C7 5.0(2) . . . . ?
C2 C1 C6 C7 -174.01(13) . . . . ?
C5 C6 C7 N1 120.99(16) . . . . ?
C1 C6 C7 N1 -62.38(18) . . . . ?
C6 C7 N1 C8 -76.83(15) . . . . ?
C6 C7 N1 C9 164.08(12) . . . . ?
C6 C7 N1 V 48.26(14) . . . . ?
C8 N1 C9 C10 165.66(12) . . . . ?
C7 N1 C9 C10 -75.61(15) . . . . ?
V N1 C9 C10 45.91(13) . . . . ?
N1 C9 C10 N2 -48.79(17) . . . . ?
C9 C10 N2 C11 144.06(13) . . . . ?
C9 C10 N2 C12 -98.22(15) . . . . ?
C9 C10 N2 V 23.41(15) . . . . ?
C11 N2 C12 C18 176.80(13) . . . . ?
C10 N2 C12 C18 57.66(17) . . . . ?
V N2 C12 C18 -63.88(14) . . . . ?
V O2 C13 C14 162.50(11) . . . . ?
V O2 C13 C18 -15.2(2) . . . . ?
O2 C13 C14 C15 -179.37(13) . . . . ?
C18 C13 C14 C15 -1.5(2) . . . . ?
C13 C14 C15 C16 -0.5(2) . . . . ?
C14 C15 C16 C17 1.6(2) . . . . ?
C14 C15 C16 C20 179.79(15) . . . . ?
C15 C16 C17 C18 -0.6(2) . . . . ?
C20 C16 C17 C18 -178.81(15) . . . . ?
C16 C17 C18 C13 -1.4(2) . . . . ?
C16 C17 C18 C12 -179.23(14) . . . . ?
O2 C13 C18 C17 -179.76(13) . . . . ?
C14 C13 C18 C17 2.5(2) . . . . ?
O2 C13 C18 C12 -2.0(2) . . . . ?
C14 C13 C18 C12 -179.76(13) . . . . ?
N2 C12 C18 C17 -135.63(14) . . . . ?
N2 C12 C18 C13 46.58(19) . . . . ?
V O3 C21 C22 10.0(2) . . . . ?
V O3 C21 C25 -171.39(10) . . . . ?
O3 C21 C22 C23 6.6(2) . . . . ?
C25 C21 C22 C23 -171.91(15) . . . . ?
V O4 C23 C22 -14.9(2) . . . . ?
V O4 C23 C24 167.35(10) . . . . ?
C21 C22 C23 O4 -4.0(3) . . . . ?
C21 C22 C23 C24 173.57(15) . . . . ?

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
C8 H8C O2 0.98 2.51 3.0735(19) 116.6 .
C11 H11C O1 0.98 2.43 2.941(2) 111.8 .
C24 H24C O1 0.98 2.51 3.487(2) 176.3 4_565

_refine_diff_density_max         0.425
_refine_diff_density_min         -0.346
_refine_diff_density_rms         0.060

_shelxl_version_number           2013-2



####################################################################### 
# 
# 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_4
_database_code_depnum_ccdc_archive 'CCDC 1997039'
loop_
_audit_author_name
_audit_author_address
'Marta S. Krawczyk '
;Faculty of Pharmacy, Wroclaw Medical University
Poland
;
_audit_update_record             
;
2020-04-15 deposited with the CCDC.	2021-03-05 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C27 H37 N2 O4 V, 0.25(C2 H3 N)'
_chemical_formula_sum            'C27.50 H37.75 N2.25 O4 V'
_chemical_formula_weight         514.79

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
V V 0.3005 0.5294 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   13.237(3)
_cell_length_b                   15.650(4)
_cell_length_c                   25.711(7)
_cell_angle_alpha                90
_cell_angle_beta                 99.83(3)
_cell_angle_gamma                90
_cell_volume                     5248(2)
_cell_formula_units_Z            8
_cell_measurement_temperature    103(2)
_cell_measurement_reflns_used    12741
_cell_measurement_theta_min      2.9
_cell_measurement_theta_max      56

_exptl_crystal_description       NEEDLE
_exptl_crystal_colour            ORANGE
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.303
_exptl_crystal_F_000             2188
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.600
_exptl_crystal_size_mid          0.130
_exptl_crystal_size_min          0.060
_exptl_absorpt_coefficient_mu    0.414
_shelx_estimated_absorpt_T_min   0.789
_shelx_estimated_absorpt_T_max   0.976
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_correction_T_min  0.842
_exptl_absorpt_correction_T_max  0.976
_exptl_absorpt_process_details   
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.33.66 (release 28-04-2010 CrysAlis171 .NET)
(compiled Apr 28 2010,14:27:37)
Analytical numeric absorption correction using a multifaceted crystal 
model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
;
_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      103(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
__diffrn_radiation_source        'normal-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'KUMA-4m4 with CCD camera'
_diffrn_measurement_method       /w
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            42392
_diffrn_reflns_av_unetI/netI     0.0965
_diffrn_reflns_av_R_equivalents  0.0830
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_theta_min         2.944
_diffrn_reflns_theta_max         28.061
_diffrn_reflns_theta_full        25.500
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             12638
_reflns_number_gt                7700
_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       'CrysAlisPro, Agilent Technologies(2011)'
_computing_cell_refinement       'CrysAlisPro, Agilent Technologies(2011)'
_computing_data_reduction        'CrysAlisPro, Agilent Technologies(2011)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_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)+(0.0500P)²]
 where P=(Fo²+2Fc²)/3
;
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         12638
_refine_ls_number_parameters     651
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0892
_refine_ls_R_factor_gt           0.0513
_refine_ls_wR_factor_ref         0.1195
_refine_ls_wR_factor_gt          0.1127
_refine_ls_goodness_of_fit_ref   1.004
_refine_ls_restrained_S_all      1.004
_refine_ls_shift/su_max          0.004
_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 0.61580(3) 0.44766(3) 0.32988(2) 0.01335(10) Uani 1 1 d . . . . .
O1A O 0.65163(13) 0.54402(10) 0.28975(7) 0.0178(4) Uani 1 1 d . . . . .
O2A O 0.59967(12) 0.35494(10) 0.37736(6) 0.0163(4) Uani 1 1 d . . . . .
N1A N 0.78182(15) 0.44584(12) 0.36536(8) 0.0148(4) Uani 1 1 d . . . . .
N2A N 0.66727(15) 0.35345(12) 0.27806(8) 0.0155(4) Uani 1 1 d . . . . .
C1A C 0.69786(19) 0.61132(15) 0.31745(10) 0.0166(5) Uani 1 1 d . . . . .
C2A C 0.64884(19) 0.69125(16) 0.31790(10) 0.0187(6) Uani 1 1 d . . . . .
C3A C 0.6997(2) 0.75504(16) 0.35022(10) 0.0194(6) Uani 1 1 d . . . . .
H3A H 0.6660 0.8083 0.3519 0.023 Uiso 1 1 calc R U . . .
C4A C 0.7966(2) 0.74482(16) 0.37993(10) 0.0221(6) Uani 1 1 d . . . . .
C5A C 0.84515(19) 0.66624(16) 0.37739(10) 0.0192(6) Uani 1 1 d . . . . .
H5A H 0.9121 0.6577 0.3969 0.023 Uiso 1 1 calc R U . . .
C6A C 0.79622(19) 0.59985(15) 0.34649(10) 0.0161(5) Uani 1 1 d . . . . .
C7A C 0.84354(18) 0.51312(15) 0.34372(10) 0.0180(5) Uani 1 1 d . . . . .
H7A1 H 0.8478 0.4996 0.3065 0.022 Uiso 1 1 calc R U . . .
H7A2 H 0.9141 0.5135 0.3641 0.022 Uiso 1 1 calc R U . . .
C8A C 0.7973(2) 0.45567(17) 0.42323(10) 0.0209(6) Uani 1 1 d . . . . .
H8A1 H 0.8700 0.4475 0.4379 0.031 Uiso 1 1 calc R U . . .
H8A2 H 0.7564 0.4129 0.4382 0.031 Uiso 1 1 calc R U . . .
H8A3 H 0.7759 0.5131 0.4321 0.031 Uiso 1 1 calc R U . . .
C9A C 0.81828(19) 0.35980(15) 0.35170(10) 0.0192(6) Uani 1 1 d . . . . .
H9A1 H 0.7939 0.3162 0.3745 0.023 Uiso 1 1 calc R U . . .
H9A2 H 0.8942 0.3588 0.3585 0.023 Uiso 1 1 calc R U . . .
C10A C 0.77955(19) 0.33781(16) 0.29408(10) 0.0199(6) Uani 1 1 d . . . . .
H10A H 0.8173 0.3725 0.2715 0.024 Uiso 1 1 calc R U . . .
H10B H 0.7941 0.2769 0.2881 0.024 Uiso 1 1 calc R U . . .
C11A C 0.6470(2) 0.38635(17) 0.22295(10) 0.0244(6) Uani 1 1 d . . . . .
H11A H 0.6838 0.4403 0.2211 0.037 Uiso 1 1 calc R U . . .
H11B H 0.5732 0.3960 0.2121 0.037 Uiso 1 1 calc R U . . .
H11C H 0.6705 0.3444 0.1993 0.037 Uiso 1 1 calc R U . . .
C12A C 0.6059(2) 0.27331(15) 0.27805(10) 0.0177(5) Uani 1 1 d . . . . .
H12A H 0.6240 0.2344 0.2507 0.021 Uiso 1 1 calc R U . . .
H12B H 0.5323 0.2877 0.2681 0.021 Uiso 1 1 calc R U . . .
C13A C 0.61456(18) 0.27006(15) 0.37703(10) 0.0159(5) Uani 1 1 d . . . . .
C14A C 0.62673(18) 0.22477(16) 0.42471(10) 0.0172(5) Uani 1 1 d . . . . .
C15A C 0.64348(19) 0.13696(16) 0.42398(11) 0.0210(6) Uani 1 1 d . . . . .
H15A H 0.6522 0.1064 0.4564 0.025 Uiso 1 1 calc R U . . .
C16A C 0.64797(19) 0.09241(16) 0.37781(11) 0.0213(6) Uani 1 1 d . . . . .
C17A C 0.63771(18) 0.13836(16) 0.33134(11) 0.0194(6) Uani 1 1 d . . . . .
H17A H 0.6417 0.1091 0.2994 0.023 Uiso 1 1 calc R U . . .
C18A C 0.62156(18) 0.22669(15) 0.33002(10) 0.0159(5) Uani 1 1 d . . . . .
C19A C 0.8479(2) 0.81523(17) 0.41485(12) 0.0336(8) Uani 1 1 d . . . . .
H19A H 0.8377 0.8698 0.3960 0.050 Uiso 1 1 calc R U . . .
H19B H 0.9214 0.8033 0.4242 0.050 Uiso 1 1 calc R U . . .
H19C H 0.8177 0.8183 0.4471 0.050 Uiso 1 1 calc R U . . .
C20A C 0.6641(2) -0.00371(16) 0.37865(12) 0.0302(7) Uani 1 1 d . . . . .
H20A H 0.5985 -0.0325 0.3789 0.045 Uiso 1 1 calc R U . . .
H20B H 0.7125 -0.0196 0.4104 0.045 Uiso 1 1 calc R U . . .
H20C H 0.6917 -0.0210 0.3472 0.045 Uiso 1 1 calc R U . . .
C21A C 0.6189(2) 0.27015(18) 0.47555(10) 0.0240(6) Uani 1 1 d . . . . .
H21A H 0.6441 0.3288 0.4740 0.036 Uiso 1 1 calc R U . . .
H21B H 0.6605 0.2400 0.5051 0.036 Uiso 1 1 calc R U . . .
H21C H 0.5472 0.2712 0.4806 0.036 Uiso 1 1 calc R U . . .
C22A C 0.54435(19) 0.70598(16) 0.28540(11) 0.0223(6) Uani 1 1 d . . . . .
H22A H 0.5099 0.7525 0.3010 0.033 Uiso 1 1 calc R U . . .
H22B H 0.5035 0.6537 0.2848 0.033 Uiso 1 1 calc R U . . .
H22C H 0.5517 0.7214 0.2493 0.033 Uiso 1 1 calc R U . . .
O3A O 0.47854(12) 0.44121(10) 0.28592(6) 0.0163(4) Uani 1 1 d . . . . .
O4A O 0.55990(12) 0.52595(10) 0.38050(7) 0.0174(4) Uani 1 1 d . . . . .
C23A C 0.31298(19) 0.47861(18) 0.24398(11) 0.0247(6) Uani 1 1 d . . . . .
H23A H 0.3330 0.5028 0.2121 0.037 Uiso 1 1 calc R U . . .
H23B H 0.2528 0.5092 0.2520 0.037 Uiso 1 1 calc R U . . .
H23C H 0.2963 0.4180 0.2382 0.037 Uiso 1 1 calc R U . . .
C24A C 0.40002(18) 0.48773(16) 0.28944(10) 0.0171(5) Uani 1 1 d . . . . .
C25A C 0.39212(18) 0.54273(15) 0.33067(10) 0.0172(5) Uani 1 1 d . . . . .
H25A H 0.3289 0.5719 0.3297 0.021 Uiso 1 1 calc R U . . .
C26A C 0.47073(19) 0.55880(15) 0.37400(10) 0.0161(5) Uani 1 1 d . . . . .
C27A C 0.4510(2) 0.61991(18) 0.41613(12) 0.0279(7) Uani 1 1 d . . . . .
H27A H 0.4699 0.5929 0.4508 0.042 Uiso 1 1 calc R U . . .
H27B H 0.3781 0.6350 0.4104 0.042 Uiso 1 1 calc R U . . .
H27C H 0.4921 0.6717 0.4147 0.042 Uiso 1 1 calc R U . . .
V2 V 0.14949(3) 0.26141(3) 0.40338(2) 0.01393(10) Uani 1 1 d . . . . .
O1B O 0.10259(12) 0.35147(10) 0.35304(6) 0.0157(4) Uani 1 1 d . . . . .
O2B O 0.21117(13) 0.16938(10) 0.44763(7) 0.0169(4) Uani 1 1 d . . . . .
N1B N 0.24882(15) 0.35809(12) 0.44743(8) 0.0154(4) Uani 1 1 d . . . . .
N2B N 0.28072(15) 0.24917(12) 0.36136(8) 0.0157(4) Uani 1 1 d . . . . .
C1B C 0.11024(18) 0.43616(15) 0.35270(10) 0.0147(5) Uani 1 1 d . . . . .
C2B C 0.07628(18) 0.48143(15) 0.30559(10) 0.0152(5) Uani 1 1 d . . . . .
C3B C 0.08061(19) 0.56999(15) 0.30508(10) 0.0182(6) Uani 1 1 d . . . . .
H3B H 0.0567 0.5995 0.2730 0.022 Uiso 1 1 calc R U . . .
C4B C 0.11906(19) 0.61709(16) 0.35022(10) 0.0191(6) Uani 1 1 d . . . . .
C5B C 0.15602(18) 0.57213(15) 0.39578(10) 0.0165(5) Uani 1 1 d . . . . .
H5B H 0.1846 0.6029 0.4266 0.020 Uiso 1 1 calc R U . . .
C6B C 0.15282(18) 0.48277(15) 0.39806(10) 0.0153(5) Uani 1 1 d . . . . .
C7B C 0.18906(19) 0.43863(15) 0.45006(10) 0.0175(5) Uani 1 1 d . . . . .
H7B1 H 0.2322 0.4792 0.4737 0.021 Uiso 1 1 calc R U . . .
H7B2 H 0.1284 0.4252 0.4664 0.021 Uiso 1 1 calc R U . . .
C8B C 0.2812(2) 0.33031(16) 0.50340(10) 0.0234(6) Uani 1 1 d . . . . .
H8B1 H 0.3202 0.2769 0.5043 0.035 Uiso 1 1 calc R U . . .
H8B2 H 0.2204 0.3211 0.5197 0.035 Uiso 1 1 calc R U . . .
H8B3 H 0.3243 0.3746 0.5229 0.035 Uiso 1 1 calc R U . . .
C9B C 0.34053(18) 0.37075(16) 0.42212(10) 0.0194(6) Uani 1 1 d . . . . .
H9B1 H 0.3998 0.3419 0.4437 0.023 Uiso 1 1 calc R U . . .
H9B2 H 0.3562 0.4326 0.4218 0.023 Uiso 1 1 calc R U . . .
C10B C 0.32763(19) 0.33670(15) 0.36571(10) 0.0179(5) Uani 1 1 d . . . . .
H10C H 0.2834 0.3762 0.3418 0.021 Uiso 1 1 calc R U . . .
H10D H 0.3954 0.3345 0.3544 0.021 Uiso 1 1 calc R U . . .
C11B C 0.2478(2) 0.22783(17) 0.30499(10) 0.0208(6) Uani 1 1 d . . . . .
H11D H 0.3069 0.2307 0.2867 0.031 Uiso 1 1 calc R U . . .
H11E H 0.1955 0.2687 0.2890 0.031 Uiso 1 1 calc R U . . .
H11F H 0.2191 0.1700 0.3019 0.031 Uiso 1 1 calc R U . . .
C12B C 0.35992(18) 0.18593(15) 0.38548(10) 0.0167(5) Uani 1 1 d . . . . .
H12C H 0.3956 0.2087 0.4196 0.020 Uiso 1 1 calc R U . . .
H12D H 0.4114 0.1792 0.3620 0.020 Uiso 1 1 calc R U . . .
C13B C 0.24248(18) 0.09679(15) 0.42771(10) 0.0158(5) Uani 1 1 d . . . . .
C14B C 0.20519(19) 0.01654(16) 0.44125(10) 0.0179(5) Uani 1 1 d . . . . .
C15B C 0.24439(19) -0.05648(16) 0.42115(10) 0.0189(6) Uani 1 1 d . . . . .
H15B H 0.2196 -0.1105 0.4303 0.023 Uiso 1 1 calc R U . . .
C16B C 0.31810(19) -0.05477(16) 0.38833(10) 0.0181(5) Uani 1 1 d . . . . .
C17B C 0.35276(19) 0.02504(16) 0.37520(10) 0.0187(6) Uani 1 1 d . . . . .
H17B H 0.4024 0.0286 0.3526 0.022 Uiso 1 1 calc R U . . .
C18B C 0.31601(18) 0.09966(15) 0.39456(10) 0.0162(5) Uani 1 1 d . . . . .
C19B C 0.1204(2) 0.71394(16) 0.34890(12) 0.0265(6) Uani 1 1 d . . . . .
H19D H 0.0499 0.7356 0.3439 0.040 Uiso 1 1 calc R U . . .
H19E H 0.1534 0.7332 0.3196 0.040 Uiso 1 1 calc R U . . .
H19F H 0.1587 0.7357 0.3823 0.040 Uiso 1 1 calc R U . . .
C20B C 0.3597(2) -0.13626(17) 0.36852(11) 0.0261(6) Uani 1 1 d . . . . .
H20D H 0.3186 -0.1519 0.3345 0.039 Uiso 1 1 calc R U . . .
H20E H 0.3564 -0.1822 0.3941 0.039 Uiso 1 1 calc R U . . .
H20F H 0.4311 -0.1274 0.3642 0.039 Uiso 1 1 calc R U . . .
C21B C 0.1267(2) 0.01086(16) 0.47668(10) 0.0219(6) Uani 1 1 d . . . . .
H21D H 0.1134 -0.0493 0.4837 0.033 Uiso 1 1 calc R U . . .
H21E H 0.0630 0.0381 0.4595 0.033 Uiso 1 1 calc R U . . .
H21F H 0.1522 0.0400 0.5101 0.033 Uiso 1 1 calc R U . . .
C22B C 0.0345(2) 0.43185(16) 0.25624(10) 0.0200(6) Uani 1 1 d . . . . .
H22D H 0.0050 0.4716 0.2283 0.030 Uiso 1 1 calc R U . . .
H22E H -0.0188 0.3924 0.2636 0.030 Uiso 1 1 calc R U . . .
H22F H 0.0900 0.3994 0.2448 0.030 Uiso 1 1 calc R U . . .
O3B O 0.05833(13) 0.17731(10) 0.35989(7) 0.0175(4) Uani 1 1 d . . . . .
O4B O 0.04470(12) 0.28058(10) 0.44886(7) 0.0173(4) Uani 1 1 d . . . . .
C23B C -0.0649(2) 0.06778(17) 0.33967(11) 0.0296(7) Uani 1 1 d . . . . .
H23D H -0.0757 0.0833 0.3022 0.044 Uiso 1 1 calc R U . . .
H23E H -0.1305 0.0513 0.3495 0.044 Uiso 1 1 calc R U . . .
H23F H -0.0170 0.0197 0.3459 0.044 Uiso 1 1 calc R U . . .
C24B C -0.02135(19) 0.14307(15) 0.37240(10) 0.0179(6) Uani 1 1 d . . . . .
C25B C -0.06892(19) 0.16934(15) 0.41436(10) 0.0173(5) Uani 1 1 d . . . . .
H25B H -0.1294 0.1398 0.4192 0.021 Uiso 1 1 calc R U . . .
C26B C -0.03525(18) 0.23499(16) 0.44965(10) 0.0164(5) Uani 1 1 d . . . . .
C27B C -0.09568(19) 0.25534(17) 0.49269(10) 0.0219(6) Uani 1 1 d . . . . .
H27D H -0.0645 0.2265 0.5253 0.033 Uiso 1 1 calc R U . . .
H27E H -0.1665 0.2355 0.4822 0.033 Uiso 1 1 calc R U . . .
H27F H -0.0954 0.3172 0.4985 0.033 Uiso 1 1 calc R U . . .
N1 N 0.5525(4) -0.1463(5) 0.4699(2) 0.0531(17) Uani 0.5 1 d . . P A -1
C1 C 0.5278(5) -0.0820(5) 0.4826(3) 0.0400(15) Uani 0.5 1 d . . P A -1
C2 C 0.4897(10) 0.0044(12) 0.5009(8) 0.0400(15) Uani 0.5 1 d . . P A -1
H2A H 0.4146 0.0055 0.4939 0.060 Uiso 0.5 1 calc R U P A -1
H2B H 0.5163 0.0510 0.4816 0.060 Uiso 0.5 1 calc R U P A -1
H2C H 0.5141 0.0115 0.5389 0.060 Uiso 0.5 1 calc R U P A -1


_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 O1A 1.9314(18) . ?
V1 O2A 1.9315(17) . ?
V1 O3A 1.9717(17) . ?
V1 O4A 2.0176(18) . ?
V1 N2A 2.173(2) . ?
V1 N1A 2.231(2) . ?
O1A C1A 1.357(3) . ?
O2A C13A 1.343(3) . ?
N1A C8A 1.475(3) . ?
N1A C9A 1.492(3) . ?
N1A C7A 1.497(3) . ?
N2A C11A 1.488(3) . ?
N2A C10A 1.493(3) . ?
N2A C12A 1.494(3) . ?
C1A C6A 1.397(3) . ?
C1A C2A 1.410(3) . ?
C2A C3A 1.396(4) . ?
C2A C22A 1.507(3) . ?
C3A C4A 1.386(4) . ?
C3A H3A 0.9500 . ?
C4A C5A 1.394(4) . ?
C4A C19A 1.507(4) . ?
C5A C6A 1.398(3) . ?
C5A H5A 0.9500 . ?
C6A C7A 1.502(3) . ?
C7A H7A1 0.9900 . ?
C7A H7A2 0.9900 . ?
C8A H8A1 0.9800 . ?
C8A H8A2 0.9800 . ?
C8A H8A3 0.9800 . ?
C9A C10A 1.522(4) . ?
C9A H9A1 0.9900 . ?
C9A H9A2 0.9900 . ?
C10A H10A 0.9900 . ?
C10A H10B 0.9900 . ?
C11A H11A 0.9800 . ?
C11A H11B 0.9800 . ?
C11A H11C 0.9800 . ?
C12A C18A 1.505(3) . ?
C12A H12A 0.9900 . ?
C12A H12B 0.9900 . ?
C13A C14A 1.401(3) . ?
C13A C18A 1.403(3) . ?
C14A C15A 1.393(3) . ?
C14A C21A 1.507(4) . ?
C15A C16A 1.387(4) . ?
C15A H15A 0.9500 . ?
C16A C17A 1.381(4) . ?
C16A C20A 1.519(3) . ?
C17A C18A 1.398(3) . ?
C17A H17A 0.9500 . ?
C19A H19A 0.9800 . ?
C19A H19B 0.9800 . ?
C19A H19C 0.9800 . ?
C20A H20A 0.9800 . ?
C20A H20B 0.9800 . ?
C20A H20C 0.9800 . ?
C21A H21A 0.9800 . ?
C21A H21B 0.9800 . ?
C21A H21C 0.9800 . ?
C22A H22A 0.9800 . ?
C22A H22B 0.9800 . ?
C22A H22C 0.9800 . ?
O3A C24A 1.285(3) . ?
O4A C26A 1.272(3) . ?
C23A C24A 1.501(3) . ?
C23A H23A 0.9800 . ?
C23A H23B 0.9800 . ?
C23A H23C 0.9800 . ?
C24A C25A 1.383(4) . ?
C25A C26A 1.411(3) . ?
C25A H25A 0.9500 . ?
C26A C27A 1.501(4) . ?
C27A H27A 0.9800 . ?
C27A H27B 0.9800 . ?
C27A H27C 0.9800 . ?
V2 O2B 1.9282(17) . ?
V2 O1B 1.9425(17) . ?
V2 O4B 1.9837(19) . ?
V2 O3B 1.9945(17) . ?
V2 N1B 2.189(2) . ?
V2 N2B 2.205(2) . ?
O1B C1B 1.329(3) . ?
O2B C13B 1.340(3) . ?
N1B C9B 1.485(3) . ?
N1B C8B 1.494(3) . ?
N1B C7B 1.496(3) . ?
N2B C11B 1.479(3) . ?
N2B C12B 1.497(3) . ?
N2B C10B 1.500(3) . ?
C1B C6B 1.409(3) . ?
C1B C2B 1.409(3) . ?
C2B C3B 1.387(3) . ?
C2B C22B 1.509(3) . ?
C3B C4B 1.395(3) . ?
C3B H3B 0.9500 . ?
C4B C5B 1.382(3) . ?
C4B C19B 1.516(3) . ?
C5B C6B 1.401(3) . ?
C5B H5B 0.9500 . ?
C6B C7B 1.509(3) . ?
C7B H7B1 0.9900 . ?
C7B H7B2 0.9900 . ?
C8B H8B1 0.9800 . ?
C8B H8B2 0.9800 . ?
C8B H8B3 0.9800 . ?
C9B C10B 1.527(4) . ?
C9B H9B1 0.9900 . ?
C9B H9B2 0.9900 . ?
C10B H10C 0.9900 . ?
C10B H10D 0.9900 . ?
C11B H11D 0.9800 . ?
C11B H11E 0.9800 . ?
C11B H11F 0.9800 . ?
C12B C18B 1.504(3) . ?
C12B H12C 0.9900 . ?
C12B H12D 0.9900 . ?
C13B C18B 1.400(4) . ?
C13B C14B 1.415(3) . ?
C14B C15B 1.391(3) . ?
C14B C21B 1.497(4) . ?
C15B C16B 1.395(4) . ?
C15B H15B 0.9500 . ?
C16B C17B 1.392(3) . ?
C16B C20B 1.512(4) . ?
C17B C18B 1.390(3) . ?
C17B H17B 0.9500 . ?
C19B H19D 0.9800 . ?
C19B H19E 0.9800 . ?
C19B H19F 0.9800 . ?
C20B H20D 0.9800 . ?
C20B H20E 0.9800 . ?
C20B H20F 0.9800 . ?
C21B H21D 0.9800 . ?
C21B H21E 0.9800 . ?
C21B H21F 0.9800 . ?
C22B H22D 0.9800 . ?
C22B H22E 0.9800 . ?
C22B H22F 0.9800 . ?
O3B C24B 1.272(3) . ?
O4B C26B 1.279(3) . ?
C23B C24B 1.505(3) . ?
C23B H23D 0.9800 . ?
C23B H23E 0.9800 . ?
C23B H23F 0.9800 . ?
C24B C25B 1.400(4) . ?
C25B C26B 1.393(3) . ?
C25B H25B 0.9500 . ?
C26B C27B 1.506(4) . ?
C27B H27D 0.9800 . ?
C27B H27E 0.9800 . ?
C27B H27F 0.9800 . ?
N1 C1 1.124(9) . ?
C1 C2 1.54(2) . ?
C2 H2A 0.9800 . ?
C2 H2B 0.9800 . ?
C2 H2C 0.9800 . ?

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
O1A V1 O2A 171.09(7) . . ?
O1A V1 O3A 91.14(7) . . ?
O2A V1 O3A 97.67(7) . . ?
O1A V1 O4A 91.20(8) . . ?
O2A V1 O4A 87.49(7) . . ?
O3A V1 O4A 89.85(7) . . ?
O1A V1 N2A 94.06(8) . . ?
O2A V1 N2A 87.59(8) . . ?
O3A V1 N2A 88.19(7) . . ?
O4A V1 N2A 174.41(8) . . ?
O1A V1 N1A 85.06(7) . . ?
O2A V1 N1A 86.53(7) . . ?
O3A V1 N1A 168.71(8) . . ?
O4A V1 N1A 100.84(7) . . ?
N2A V1 N1A 81.49(8) . . ?
C1A O1A V1 117.09(15) . . ?
C13A O2A V1 134.97(16) . . ?
C8A N1A C9A 109.67(19) . . ?
C8A N1A C7A 108.11(19) . . ?
C9A N1A C7A 109.16(19) . . ?
C8A N1A V1 111.65(15) . . ?
C9A N1A V1 104.53(14) . . ?
C7A N1A V1 113.64(14) . . ?
C11A N2A C10A 109.2(2) . . ?
C11A N2A C12A 106.29(19) . . ?
C10A N2A C12A 112.18(18) . . ?
C11A N2A V1 108.94(15) . . ?
C10A N2A V1 110.10(14) . . ?
C12A N2A V1 110.02(15) . . ?
O1A C1A C6A 118.4(2) . . ?
O1A C1A C2A 121.7(2) . . ?
C6A C1A C2A 119.8(2) . . ?
C3A C2A C1A 117.6(2) . . ?
C3A C2A C22A 121.6(2) . . ?
C1A C2A C22A 120.7(2) . . ?
C4A C3A C2A 123.5(2) . . ?
C4A C3A H3A 118.2 . . ?
C2A C3A H3A 118.2 . . ?
C3A C4A C5A 117.8(2) . . ?
C3A C4A C19A 121.6(2) . . ?
C5A C4A C19A 120.6(2) . . ?
C4A C5A C6A 120.6(2) . . ?
C4A C5A H5A 119.7 . . ?
C6A C5A H5A 119.7 . . ?
C1A C6A C5A 120.5(2) . . ?
C1A C6A C7A 116.7(2) . . ?
C5A C6A C7A 122.8(2) . . ?
N1A C7A C6A 111.1(2) . . ?
N1A C7A H7A1 109.4 . . ?
C6A C7A H7A1 109.4 . . ?
N1A C7A H7A2 109.4 . . ?
C6A C7A H7A2 109.4 . . ?
H7A1 C7A H7A2 108.0 . . ?
N1A C8A H8A1 109.5 . . ?
N1A C8A H8A2 109.5 . . ?
H8A1 C8A H8A2 109.5 . . ?
N1A C8A H8A3 109.5 . . ?
H8A1 C8A H8A3 109.5 . . ?
H8A2 C8A H8A3 109.5 . . ?
N1A C9A C10A 111.36(19) . . ?
N1A C9A H9A1 109.4 . . ?
C10A C9A H9A1 109.4 . . ?
N1A C9A H9A2 109.4 . . ?
C10A C9A H9A2 109.4 . . ?
H9A1 C9A H9A2 108.0 . . ?
N2A C10A C9A 112.7(2) . . ?
N2A C10A H10A 109.1 . . ?
C9A C10A H10A 109.1 . . ?
N2A C10A H10B 109.1 . . ?
C9A C10A H10B 109.1 . . ?
H10A C10A H10B 107.8 . . ?
N2A C11A H11A 109.5 . . ?
N2A C11A H11B 109.5 . . ?
H11A C11A H11B 109.5 . . ?
N2A C11A H11C 109.5 . . ?
H11A C11A H11C 109.5 . . ?
H11B C11A H11C 109.5 . . ?
N2A C12A C18A 114.49(19) . . ?
N2A C12A H12A 108.6 . . ?
C18A C12A H12A 108.6 . . ?
N2A C12A H12B 108.6 . . ?
C18A C12A H12B 108.6 . . ?
H12A C12A H12B 107.6 . . ?
O2A C13A C14A 119.3(2) . . ?
O2A C13A C18A 121.0(2) . . ?
C14A C13A C18A 119.6(2) . . ?
C15A C14A C13A 118.8(2) . . ?
C15A C14A C21A 120.8(2) . . ?
C13A C14A C21A 120.4(2) . . ?
C16A C15A C14A 122.5(2) . . ?
C16A C15A H15A 118.7 . . ?
C14A C15A H15A 118.7 . . ?
C17A C16A C15A 117.8(2) . . ?
C17A C16A C20A 121.4(3) . . ?
C15A C16A C20A 120.8(2) . . ?
C16A C17A C18A 121.9(3) . . ?
C16A C17A H17A 119.1 . . ?
C18A C17A H17A 119.1 . . ?
C17A C18A C13A 119.3(2) . . ?
C17A C18A C12A 119.9(2) . . ?
C13A C18A C12A 120.7(2) . . ?
C4A C19A H19A 109.5 . . ?
C4A C19A H19B 109.5 . . ?
H19A C19A H19B 109.5 . . ?
C4A C19A H19C 109.5 . . ?
H19A C19A H19C 109.5 . . ?
H19B C19A H19C 109.5 . . ?
C16A C20A H20A 109.5 . . ?
C16A C20A H20B 109.5 . . ?
H20A C20A H20B 109.5 . . ?
C16A C20A H20C 109.5 . . ?
H20A C20A H20C 109.5 . . ?
H20B C20A H20C 109.5 . . ?
C14A C21A H21A 109.5 . . ?
C14A C21A H21B 109.5 . . ?
H21A C21A H21B 109.5 . . ?
C14A C21A H21C 109.5 . . ?
H21A C21A H21C 109.5 . . ?
H21B C21A H21C 109.5 . . ?
C2A C22A H22A 109.5 . . ?
C2A C22A H22B 109.5 . . ?
H22A C22A H22B 109.5 . . ?
C2A C22A H22C 109.5 . . ?
H22A C22A H22C 109.5 . . ?
H22B C22A H22C 109.5 . . ?
C24A O3A V1 127.44(15) . . ?
C26A O4A V1 126.51(16) . . ?
C24A C23A H23A 109.5 . . ?
C24A C23A H23B 109.5 . . ?
H23A C23A H23B 109.5 . . ?
C24A C23A H23C 109.5 . . ?
H23A C23A H23C 109.5 . . ?
H23B C23A H23C 109.5 . . ?
O3A C24A C25A 125.1(2) . . ?
O3A C24A C23A 114.4(2) . . ?
C25A C24A C23A 120.5(2) . . ?
C24A C25A C26A 125.0(2) . . ?
C24A C25A H25A 117.5 . . ?
C26A C25A H25A 117.5 . . ?
O4A C26A C25A 125.0(2) . . ?
O4A C26A C27A 115.8(2) . . ?
C25A C26A C27A 119.2(2) . . ?
C26A C27A H27A 109.5 . . ?
C26A C27A H27B 109.5 . . ?
H27A C27A H27B 109.5 . . ?
C26A C27A H27C 109.5 . . ?
H27A C27A H27C 109.5 . . ?
H27B C27A H27C 109.5 . . ?
O2B V2 O1B 171.94(8) . . ?
O2B V2 O4B 91.92(7) . . ?
O1B V2 O4B 96.14(7) . . ?
O2B V2 O3B 89.58(7) . . ?
O1B V2 O3B 90.64(7) . . ?
O4B V2 O3B 90.76(7) . . ?
O2B V2 N1B 93.13(8) . . ?
O1B V2 N1B 86.48(7) . . ?
O4B V2 N1B 90.53(7) . . ?
O3B V2 N1B 176.96(7) . . ?
O2B V2 N2B 86.25(7) . . ?
O1B V2 N2B 85.72(7) . . ?
O4B V2 N2B 172.13(7) . . ?
O3B V2 N2B 96.88(8) . . ?
N1B V2 N2B 81.94(8) . . ?
C1B O1B V2 135.37(15) . . ?
C13B O2B V2 122.34(15) . . ?
C9B N1B C8B 109.80(19) . . ?
C9B N1B C7B 112.67(19) . . ?
C8B N1B C7B 105.59(19) . . ?
C9B N1B V2 109.22(15) . . ?
C8B N1B V2 110.22(15) . . ?
C7B N1B V2 109.29(14) . . ?
C11B N2B C12B 108.96(19) . . ?
C11B N2B C10B 109.16(19) . . ?
C12B N2B C10B 108.73(18) . . ?
C11B N2B V2 112.03(15) . . ?
C12B N2B V2 114.14(15) . . ?
C10B N2B V2 103.58(14) . . ?
O1B C1B C6B 122.1(2) . . ?
O1B C1B C2B 119.6(2) . . ?
C6B C1B C2B 118.4(2) . . ?
C3B C2B C1B 120.2(2) . . ?
C3B C2B C22B 121.0(2) . . ?
C1B C2B C22B 118.8(2) . . ?
C2B C3B C4B 122.0(2) . . ?
C2B C3B H3B 119.0 . . ?
C4B C3B H3B 119.0 . . ?
C5B C4B C3B 117.5(2) . . ?
C5B C4B C19B 121.6(2) . . ?
C3B C4B C19B 120.9(2) . . ?
C4B C5B C6B 122.3(2) . . ?
C4B C5B H5B 118.8 . . ?
C6B C5B H5B 118.8 . . ?
C5B C6B C1B 119.5(2) . . ?
C5B C6B C7B 119.1(2) . . ?
C1B C6B C7B 121.2(2) . . ?
N1B C7B C6B 115.9(2) . . ?
N1B C7B H7B1 108.3 . . ?
C6B C7B H7B1 108.3 . . ?
N1B C7B H7B2 108.3 . . ?
C6B C7B H7B2 108.3 . . ?
H7B1 C7B H7B2 107.4 . . ?
N1B C8B H8B1 109.5 . . ?
N1B C8B H8B2 109.5 . . ?
H8B1 C8B H8B2 109.5 . . ?
N1B C8B H8B3 109.5 . . ?
H8B1 C8B H8B3 109.5 . . ?
H8B2 C8B H8B3 109.5 . . ?
N1B C9B C10B 113.7(2) . . ?
N1B C9B H9B1 108.8 . . ?
C10B C9B H9B1 108.8 . . ?
N1B C9B H9B2 108.8 . . ?
C10B C9B H9B2 108.8 . . ?
H9B1 C9B H9B2 107.7 . . ?
N2B C10B C9B 111.5(2) . . ?
N2B C10B H10C 109.3 . . ?
C9B C10B H10C 109.3 . . ?
N2B C10B H10D 109.3 . . ?
C9B C10B H10D 109.3 . . ?
H10C C10B H10D 108.0 . . ?
N2B C11B H11D 109.5 . . ?
N2B C11B H11E 109.5 . . ?
H11D C11B H11E 109.5 . . ?
N2B C11B H11F 109.5 . . ?
H11D C11B H11F 109.5 . . ?
H11E C11B H11F 109.5 . . ?
N2B C12B C18B 113.33(19) . . ?
N2B C12B H12C 108.9 . . ?
C18B C12B H12C 108.9 . . ?
N2B C12B H12D 108.9 . . ?
C18B C12B H12D 108.9 . . ?
H12C C12B H12D 107.7 . . ?
O2B C13B C18B 119.9(2) . . ?
O2B C13B C14B 121.0(2) . . ?
C18B C13B C14B 119.1(2) . . ?
C15B C14B C13B 118.0(2) . . ?
C15B C14B C21B 121.3(2) . . ?
C13B C14B C21B 120.7(2) . . ?
C14B C15B C16B 123.6(2) . . ?
C14B C15B H15B 118.2 . . ?
C16B C15B H15B 118.2 . . ?
C17B C16B C15B 117.2(2) . . ?
C17B C16B C20B 121.4(2) . . ?
C15B C16B C20B 121.3(2) . . ?
C18B C17B C16B 121.1(2) . . ?
C18B C17B H17B 119.4 . . ?
C16B C17B H17B 119.4 . . ?
C17B C18B C13B 120.9(2) . . ?
C17B C18B C12B 122.1(2) . . ?
C13B C18B C12B 116.8(2) . . ?
C4B C19B H19D 109.5 . . ?
C4B C19B H19E 109.5 . . ?
H19D C19B H19E 109.5 . . ?
C4B C19B H19F 109.5 . . ?
H19D C19B H19F 109.5 . . ?
H19E C19B H19F 109.5 . . ?
C16B C20B H20D 109.5 . . ?
C16B C20B H20E 109.5 . . ?
H20D C20B H20E 109.5 . . ?
C16B C20B H20F 109.5 . . ?
H20D C20B H20F 109.5 . . ?
H20E C20B H20F 109.5 . . ?
C14B C21B H21D 109.5 . . ?
C14B C21B H21E 109.5 . . ?
H21D C21B H21E 109.5 . . ?
C14B C21B H21F 109.5 . . ?
H21D C21B H21F 109.5 . . ?
H21E C21B H21F 109.5 . . ?
C2B C22B H22D 109.5 . . ?
C2B C22B H22E 109.5 . . ?
H22D C22B H22E 109.5 . . ?
C2B C22B H22F 109.5 . . ?
H22D C22B H22F 109.5 . . ?
H22E C22B H22F 109.5 . . ?
C24B O3B V2 125.76(16) . . ?
C26B O4B V2 126.06(16) . . ?
C24B C23B H23D 109.5 . . ?
C24B C23B H23E 109.5 . . ?
H23D C23B H23E 109.5 . . ?
C24B C23B H23F 109.5 . . ?
H23D C23B H23F 109.5 . . ?
H23E C23B H23F 109.5 . . ?
O3B C24B C25B 124.9(2) . . ?
O3B C24B C23B 116.3(2) . . ?
C25B C24B C23B 118.7(2) . . ?
C26B C25B C24B 125.6(2) . . ?
C26B C25B H25B 117.2 . . ?
C24B C25B H25B 117.2 . . ?
O4B C26B C25B 125.1(2) . . ?
O4B C26B C27B 116.0(2) . . ?
C25B C26B C27B 118.9(2) . . ?
C26B C27B H27D 109.5 . . ?
C26B C27B H27E 109.5 . . ?
H27D C27B H27E 109.5 . . ?
C26B C27B H27F 109.5 . . ?
H27D C27B H27F 109.5 . . ?
H27E C27B H27F 109.5 . . ?
N1 C1 C2 177.4(9) . . ?
C1 C2 H2A 109.5 . . ?
C1 C2 H2B 109.5 . . ?
H2A C2 H2B 109.5 . . ?
C1 C2 H2C 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?

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
V1 O1A C1A C6A 66.6(3) . . . . ?
V1 O1A C1A C2A -112.8(2) . . . . ?
O1A C1A C2A C3A 176.0(2) . . . . ?
C6A C1A C2A C3A -3.4(4) . . . . ?
O1A C1A C2A C22A -2.8(4) . . . . ?
C6A C1A C2A C22A 177.9(2) . . . . ?
C1A C2A C3A C4A 2.6(4) . . . . ?
C22A C2A C3A C4A -178.7(3) . . . . ?
C2A C3A C4A C5A -0.4(4) . . . . ?
C2A C3A C4A C19A -179.1(3) . . . . ?
C3A C4A C5A C6A -1.1(4) . . . . ?
C19A C4A C5A C6A 177.7(3) . . . . ?
O1A C1A C6A C5A -177.3(2) . . . . ?
C2A C1A C6A C5A 2.1(4) . . . . ?
O1A C1A C6A C7A 1.0(4) . . . . ?
C2A C1A C6A C7A -179.6(2) . . . . ?
C4A C5A C6A C1A 0.2(4) . . . . ?
C4A C5A C6A C7A -178.0(2) . . . . ?
C8A N1A C7A C6A -72.5(2) . . . . ?
C9A N1A C7A C6A 168.24(19) . . . . ?
V1 N1A C7A C6A 52.0(2) . . . . ?
C1A C6A C7A N1A -62.1(3) . . . . ?
C5A C6A C7A N1A 116.2(3) . . . . ?
C8A N1A C9A C10A 165.4(2) . . . . ?
C7A N1A C9A C10A -76.3(2) . . . . ?
V1 N1A C9A C10A 45.6(2) . . . . ?
C11A N2A C10A C9A 143.2(2) . . . . ?
C12A N2A C10A C9A -99.2(2) . . . . ?
V1 N2A C10A C9A 23.7(2) . . . . ?
N1A C9A C10A N2A -48.4(3) . . . . ?
C11A N2A C12A C18A 176.2(2) . . . . ?
C10A N2A C12A C18A 56.9(3) . . . . ?
V1 N2A C12A C18A -66.0(2) . . . . ?
V1 O2A C13A C14A 159.63(17) . . . . ?
V1 O2A C13A C18A -18.2(3) . . . . ?
O2A C13A C14A C15A -179.2(2) . . . . ?
C18A C13A C14A C15A -1.3(4) . . . . ?
O2A C13A C14A C21A 2.5(3) . . . . ?
C18A C13A C14A C21A -179.7(2) . . . . ?
C13A C14A C15A C16A -0.4(4) . . . . ?
C21A C14A C15A C16A 178.0(2) . . . . ?
C14A C15A C16A C17A 1.6(4) . . . . ?
C14A C15A C16A C20A -178.7(2) . . . . ?
C15A C16A C17A C18A -1.1(4) . . . . ?
C20A C16A C17A C18A 179.2(2) . . . . ?
C16A C17A C18A C13A -0.6(4) . . . . ?
C16A C17A C18A C12A -177.2(2) . . . . ?
O2A C13A C18A C17A 179.6(2) . . . . ?
C14A C13A C18A C17A 1.8(4) . . . . ?
O2A C13A C18A C12A -3.9(4) . . . . ?
C14A C13A C18A C12A 178.3(2) . . . . ?
N2A C12A C18A C17A -133.5(2) . . . . ?
N2A C12A C18A C13A 50.1(3) . . . . ?
V1 O3A C24A C25A -11.1(4) . . . . ?
V1 O3A C24A C23A 168.84(16) . . . . ?
O3A C24A C25A C26A 2.8(4) . . . . ?
C23A C24A C25A C26A -177.1(2) . . . . ?
V1 O4A C26A C25A 3.3(3) . . . . ?
V1 O4A C26A C27A -175.86(17) . . . . ?
C24A C25A C26A O4A 1.2(4) . . . . ?
C24A C25A C26A C27A -179.6(2) . . . . ?
V2 O1B C1B C6B -6.9(4) . . . . ?
V2 O1B C1B C2B 172.18(17) . . . . ?
O1B C1B C2B C3B 177.8(2) . . . . ?
C6B C1B C2B C3B -3.0(4) . . . . ?
O1B C1B C2B C22B -1.6(4) . . . . ?
C6B C1B C2B C22B 177.6(2) . . . . ?
C1B C2B C3B C4B 0.7(4) . . . . ?
C22B C2B C3B C4B -179.9(2) . . . . ?
C2B C3B C4B C5B 1.9(4) . . . . ?
C2B C3B C4B C19B -178.4(2) . . . . ?
C3B C4B C5B C6B -2.1(4) . . . . ?
C19B C4B C5B C6B 178.2(2) . . . . ?
C4B C5B C6B C1B -0.3(4) . . . . ?
C4B C5B C6B C7B -176.5(2) . . . . ?
O1B C1B C6B C5B -178.1(2) . . . . ?
C2B C1B C6B C5B 2.8(4) . . . . ?
O1B C1B C6B C7B -2.0(4) . . . . ?
C2B C1B C6B C7B 178.9(2) . . . . ?
C9B N1B C7B C6B 56.6(3) . . . . ?
C8B N1B C7B C6B 176.4(2) . . . . ?
V2 N1B C7B C6B -65.1(2) . . . . ?
C5B C6B C7B N1B -140.6(2) . . . . ?
C1B C6B C7B N1B 43.3(3) . . . . ?
C8B N1B C9B C10B 138.4(2) . . . . ?
C7B N1B C9B C10B -104.2(2) . . . . ?
V2 N1B C9B C10B 17.4(2) . . . . ?
C11B N2B C10B C9B 166.9(2) . . . . ?
C12B N2B C10B C9B -74.4(3) . . . . ?
V2 N2B C10B C9B 47.4(2) . . . . ?
N1B C9B C10B N2B -45.6(3) . . . . ?
C11B N2B C12B C18B -74.2(3) . . . . ?
C10B N2B C12B C18B 166.9(2) . . . . ?
V2 N2B C12B C18B 51.8(2) . . . . ?
V2 O2B C13B C18B 58.6(3) . . . . ?
V2 O2B C13B C14B -123.8(2) . . . . ?
O2B C13B C14B C15B -177.1(2) . . . . ?
C18B C13B C14B C15B 0.6(3) . . . . ?
O2B C13B C14B C21B 2.3(3) . . . . ?
C18B C13B C14B C21B 179.9(2) . . . . ?
C13B C14B C15B C16B -0.2(4) . . . . ?
C21B C14B C15B C16B -179.5(2) . . . . ?
C14B C15B C16B C17B -0.4(4) . . . . ?
C14B C15B C16B C20B 178.7(2) . . . . ?
C15B C16B C17B C18B 0.7(3) . . . . ?
C20B C16B C17B C18B -178.4(2) . . . . ?
C16B C17B C18B C13B -0.3(4) . . . . ?
C16B C17B C18B C12B 173.6(2) . . . . ?
O2B C13B C18B C17B 177.3(2) . . . . ?
C14B C13B C18B C17B -0.3(3) . . . . ?
O2B C13B C18B C12B 3.0(3) . . . . ?
C14B C13B C18B C12B -174.6(2) . . . . ?
N2B C12B C18B C17B 126.3(2) . . . . ?
N2B C12B C18B C13B -59.5(3) . . . . ?
V2 O3B C24B C25B 11.8(3) . . . . ?
V2 O3B C24B C23B -167.01(17) . . . . ?
O3B C24B C25B C26B -1.9(4) . . . . ?
C23B C24B C25B C26B 176.8(2) . . . . ?
V2 O4B C26B C25B -7.7(3) . . . . ?
V2 O4B C26B C27B 172.06(15) . . . . ?
C24B C25B C26B O4B -0.4(4) . . . . ?
C24B C25B C26B C27B 179.9(2) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C8A H8A2 O2A 0.98 2.54 3.109(3) 116.8 .
C11A H11A O1A 0.98 2.49 3.001(3) 112.4 .
C11A H11B O3A 0.98 2.55 3.092(3) 115.1 .
C7B H7B2 O4B 0.99 2.53 3.123(3) 118.5 .
C23B H23D O1A 0.98 2.48 3.350(3) 147.3 2_545

_refine_diff_density_max         0.406
_refine_diff_density_min         -0.561
_refine_diff_density_rms         0.090

_shelxl_version_number           2013-2



####################################################################### 
# 
# 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 1997043'
loop_
_audit_author_name
_audit_author_address
'Marta S. Krawczyk '
;Faculty of Pharmacy, Wroclaw Medical University
Poland
;
_audit_update_record             
;
2020-04-15 deposited with the CCDC.	2021-03-05 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C22 H30 N2 O3 V'
_chemical_formula_weight         421.42

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
V V 0.3005 0.5294 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   13.376(5)
_cell_length_b                   11.010(3)
_cell_length_c                   15.427(6)
_cell_angle_alpha                90
_cell_angle_beta                 113.00(4)
_cell_angle_gamma                90
_cell_volume                     2091.3(14)
_cell_formula_units_Z            4
_cell_measurement_temperature    101(2)
_cell_measurement_reflns_used    25764
_cell_measurement_theta_min      2
_cell_measurement_theta_max      37

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            VIOLET
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.338
_exptl_crystal_F_000             892
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.600
_exptl_crystal_size_mid          0.530
_exptl_crystal_size_min          0.400
_exptl_absorpt_coefficient_mu    0.499
_shelx_estimated_absorpt_T_min   0.754
_shelx_estimated_absorpt_T_max   0.825
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_correction_T_min  0.775
_exptl_absorpt_correction_T_max  0.849
_exptl_absorpt_process_details   
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.32.5
Analytical numeric absorption correction using a
multifaceted crystal model based on expressions
derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
;
_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      101(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'normal-focus sealed tube'
_diffrn_measurement_device_type  
;
Kuma KM4 diffractometer with a CCD detector
;
_diffrn_measurement_method       w/
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            34826
_diffrn_reflns_av_unetI/netI     0.0325
_diffrn_reflns_av_R_equivalents  0.0558
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         2.869
_diffrn_reflns_theta_max         36.945
_diffrn_reflns_theta_full        25.500
_diffrn_measured_fraction_theta_max 0.959
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.959
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.959
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             10167
_reflns_number_gt                8559
_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 PRO (Agilent, 2011)'
_computing_cell_refinement       'CrysAlis PRO (Agilent, 2011)'
_computing_data_reduction        'CrysAlis PRO (Agilent, 2011)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_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)+(0.0951P)²+0.2060P]
 where P=(Fo²+2Fc²)/3
;
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         10167
_refine_ls_number_parameters     259
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0549
_refine_ls_R_factor_gt           0.0478
_refine_ls_wR_factor_ref         0.1430
_refine_ls_wR_factor_gt          0.1382
_refine_ls_goodness_of_fit_ref   1.093
_refine_ls_restrained_S_all      1.093
_refine_ls_shift/su_max          0.002
_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
V V 0.56409(2) 0.61098(2) 0.67611(2) 0.01264(5) Uani 1 1 d . . . . .
O2 O 0.62759(6) 0.70675(7) 0.75720(6) 0.02074(14) Uani 1 1 d . . . . .
O1 O 0.41215(6) 0.63967(7) 0.62046(5) 0.01666(12) Uani 1 1 d . . . . .
C1 C 0.33201(8) 0.61407(8) 0.64853(7) 0.01472(15) Uani 1 1 d . . . . .
C2 C 0.24144(8) 0.69192(9) 0.62260(7) 0.01725(16) Uani 1 1 d . . . . .
C3 C 0.15665(8) 0.66104(10) 0.64978(7) 0.01983(17) Uani 1 1 d . . . . .
H3 H 0.0951 0.7129 0.6318 0.024 Uiso 1 1 calc R U . . .
C4 C 0.15847(8) 0.55733(11) 0.70216(7) 0.02040(18) Uani 1 1 d . . . . .
C5 C 0.24785(8) 0.48010(10) 0.72538(7) 0.01908(17) Uani 1 1 d . . . . .
H5 H 0.2507 0.4084 0.7605 0.023 Uiso 1 1 calc R U . . .
C6 C 0.33295(7) 0.50652(9) 0.69782(6) 0.01538(15) Uani 1 1 d . . . . .
C7 C 0.42218(7) 0.41657(8) 0.71199(7) 0.01546(15) Uani 1 1 d . . . . .
H7A H 0.4126 0.3468 0.7485 0.019 Uiso 1 1 calc R U . . .
H7B H 0.4158 0.3857 0.6497 0.019 Uiso 1 1 calc R U . . .
N1 N 0.53352(6) 0.46775(7) 0.76217(5) 0.01396(13) Uani 1 1 d . . . . .
C8 C 0.54332(9) 0.51479(10) 0.85586(7) 0.02063(18) Uani 1 1 d . . . . .
H8A H 0.4910 0.5807 0.8469 0.031 Uiso 1 1 calc R U . . .
H8B H 0.6171 0.5455 0.8903 0.031 Uiso 1 1 calc R U . . .
H8C H 0.5283 0.4491 0.8919 0.031 Uiso 1 1 calc R U . . .
C9 C 0.61471(8) 0.36898(9) 0.77676(7) 0.01784(16) Uani 1 1 d . . . . .
H9A H 0.5840 0.2907 0.7864 0.021 Uiso 1 1 calc R U . . .
H9B H 0.6806 0.3863 0.8337 0.021 Uiso 1 1 calc R U . . .
C10 C 0.64428(8) 0.36005(9) 0.69171(7) 0.01711(16) Uani 1 1 d . . . . .
H10A H 0.7013 0.2977 0.7029 0.021 Uiso 1 1 calc R U . . .
H10B H 0.5797 0.3356 0.6358 0.021 Uiso 1 1 calc R U . . .
N2 N 0.68468(6) 0.48063(7) 0.67435(6) 0.01377(13) Uani 1 1 d . . . . .
C11 C 0.79257(8) 0.50861(9) 0.74955(7) 0.01884(16) Uani 1 1 d . . . . .
H11A H 0.7842 0.5232 0.8090 0.028 Uiso 1 1 calc R U . . .
H11B H 0.8228 0.5812 0.7321 0.028 Uiso 1 1 calc R U . . .
H11C H 0.8417 0.4398 0.7570 0.028 Uiso 1 1 calc R U . . .
C12 C 0.69816(8) 0.47087(8) 0.58234(7) 0.01706(16) Uani 1 1 d . . . . .
H12A H 0.7587 0.4144 0.5902 0.020 Uiso 1 1 calc R U . . .
H12B H 0.6312 0.4358 0.5345 0.020 Uiso 1 1 calc R U . . .
C13 C 0.64718(8) 0.68559(8) 0.53558(6) 0.01563(15) Uani 1 1 d . . . . .
C14 C 0.66074(8) 0.79630(9) 0.49569(7) 0.01688(16) Uani 1 1 d . . . . .
C15 C 0.74609(9) 0.80783(9) 0.46610(7) 0.01934(17) Uani 1 1 d . . . . .
H15 H 0.7546 0.8821 0.4384 0.023 Uiso 1 1 calc R U . . .
C16 C 0.81972(8) 0.71376(10) 0.47583(7) 0.01928(17) Uani 1 1 d . . . . .
C17 C 0.80622(9) 0.60555(9) 0.51693(7) 0.01846(17) Uani 1 1 d . . . . .
H17 H 0.8560 0.5408 0.5248 0.022 Uiso 1 1 calc R U . . .
C18 C 0.72081(8) 0.59044(9) 0.54685(7) 0.01646(15) Uani 1 1 d . . . . .
C19 C 0.06555(9) 0.52764(14) 0.73097(9) 0.0284(2) Uani 1 1 d . . . . .
H19A H 0.0762 0.5697 0.7899 0.043 Uiso 1 1 calc R U . . .
H19B H 0.0632 0.4398 0.7402 0.043 Uiso 1 1 calc R U . . .
H19C H -0.0030 0.5542 0.6815 0.043 Uiso 1 1 calc R U . . .
C20 C 0.90823(10) 0.72879(12) 0.43889(8) 0.0262(2) Uani 1 1 d . . . . .
H20A H 0.8754 0.7420 0.3707 0.039 Uiso 1 1 calc R U . . .
H20B H 0.9532 0.6554 0.4526 0.039 Uiso 1 1 calc R U . . .
H20C H 0.9535 0.7988 0.4694 0.039 Uiso 1 1 calc R U . . .
C21 C 0.58073(10) 0.89722(9) 0.48435(8) 0.0231(2) Uani 1 1 d . . . . .
H21A H 0.6096 0.9733 0.4705 0.035 Uiso 1 1 calc R U . . .
H21B H 0.5687 0.9063 0.5427 0.035 Uiso 1 1 calc R U . . .
H21C H 0.5118 0.8778 0.4324 0.035 Uiso 1 1 calc R U . . .
C22 C 0.23672(10) 0.80208(10) 0.56343(8) 0.0238(2) Uani 1 1 d . . . . .
H22A H 0.1748 0.8528 0.5593 0.036 Uiso 1 1 calc R U . . .
H22B H 0.2282 0.7764 0.5001 0.036 Uiso 1 1 calc R U . . .
H22C H 0.3040 0.8488 0.5924 0.036 Uiso 1 1 calc R U . . .
O3 O 0.56039(6) 0.67051(7) 0.55778(5) 0.01891(13) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
V O2 1.6025(9) . ?
V O1 1.8983(12) . ?
V O3 1.9219(10) . ?
V N2 2.1672(9) . ?
V N1 2.2003(9) . ?
O1 C1 1.3337(12) . ?
C1 C6 1.4046(13) . ?
C1 C2 1.4084(14) . ?
C2 C3 1.3962(15) . ?
C2 C22 1.5044(15) . ?
C3 C4 1.3935(16) . ?
C3 H3 0.9500 . ?
C4 C5 1.3950(15) . ?
C4 C19 1.5103(15) . ?
C5 C6 1.3927(14) . ?
C5 H5 0.9500 . ?
C6 C7 1.4997(14) . ?
C7 N1 1.4946(14) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
N1 C9 1.4906(13) . ?
N1 C8 1.4921(14) . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C9 C10 1.5142(15) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 N2 1.4964(13) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
N2 C11 1.4882(15) . ?
N2 C12 1.5031(13) . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 C18 1.5014(14) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 O3 1.3428(13) . ?
C13 C18 1.4013(14) . ?
C13 C14 1.4087(13) . ?
C14 C15 1.3911(15) . ?
C14 C21 1.5048(15) . ?
C15 C16 1.3963(16) . ?
C15 H15 0.9500 . ?
C16 C17 1.3941(15) . ?
C16 C20 1.5104(15) . ?
C17 C18 1.3992(15) . ?
C17 H17 0.9500 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O2 V O1 113.00(5) . . ?
O2 V O3 109.04(5) . . ?
O1 V O3 83.57(5) . . ?
O2 V N2 105.99(5) . . ?
O1 V N2 140.81(3) . . ?
O3 V N2 87.54(4) . . ?
O2 V N1 99.63(5) . . ?
O1 V N1 88.49(4) . . ?
O3 V N1 151.13(3) . . ?
N2 V N1 81.23(4) . . ?
C1 O1 V 132.24(7) . . ?
O1 C1 C6 121.04(8) . . ?
O1 C1 C2 119.37(9) . . ?
C6 C1 C2 119.44(9) . . ?
C3 C2 C1 118.43(9) . . ?
C3 C2 C22 122.15(9) . . ?
C1 C2 C22 119.37(9) . . ?
C4 C3 C2 122.78(9) . . ?
C4 C3 H3 118.6 . . ?
C2 C3 H3 118.6 . . ?
C3 C4 C5 117.87(9) . . ?
C3 C4 C19 121.21(10) . . ?
C5 C4 C19 120.91(11) . . ?
C6 C5 C4 121.00(10) . . ?
C6 C5 H5 119.5 . . ?
C4 C5 H5 119.5 . . ?
C5 C6 C1 120.39(9) . . ?
C5 C6 C7 121.09(9) . . ?
C1 C6 C7 118.29(8) . . ?
N1 C7 C6 113.68(8) . . ?
N1 C7 H7A 108.8 . . ?
C6 C7 H7A 108.8 . . ?
N1 C7 H7B 108.8 . . ?
C6 C7 H7B 108.8 . . ?
H7A C7 H7B 107.7 . . ?
C9 N1 C8 108.90(8) . . ?
C9 N1 C7 108.84(8) . . ?
C8 N1 C7 108.98(8) . . ?
C9 N1 V 108.52(6) . . ?
C8 N1 V 111.66(6) . . ?
C7 N1 V 109.88(6) . . ?
N1 C8 H8A 109.5 . . ?
N1 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
N1 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
N1 C9 C10 109.77(8) . . ?
N1 C9 H9A 109.7 . . ?
C10 C9 H9A 109.7 . . ?
N1 C9 H9B 109.7 . . ?
C10 C9 H9B 109.7 . . ?
H9A C9 H9B 108.2 . . ?
N2 C10 C9 109.40(8) . . ?
N2 C10 H10A 109.8 . . ?
C9 C10 H10A 109.8 . . ?
N2 C10 H10B 109.8 . . ?
C9 C10 H10B 109.8 . . ?
H10A C10 H10B 108.2 . . ?
C11 N2 C10 110.62(8) . . ?
C11 N2 C12 108.26(8) . . ?
C10 N2 C12 106.89(7) . . ?
C11 N2 V 110.67(6) . . ?
C10 N2 V 105.23(6) . . ?
C12 N2 V 115.07(6) . . ?
N2 C11 H11A 109.5 . . ?
N2 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
N2 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C18 C12 N2 113.42(8) . . ?
C18 C12 H12A 108.9 . . ?
N2 C12 H12A 108.9 . . ?
C18 C12 H12B 108.9 . . ?
N2 C12 H12B 108.9 . . ?
H12A C12 H12B 107.7 . . ?
O3 C13 C18 120.77(8) . . ?
O3 C13 C14 119.34(9) . . ?
C18 C13 C14 119.79(9) . . ?
C15 C14 C13 118.99(9) . . ?
C15 C14 C21 122.14(9) . . ?
C13 C14 C21 118.85(9) . . ?
C14 C15 C16 122.12(9) . . ?
C14 C15 H15 118.9 . . ?
C16 C15 H15 118.9 . . ?
C17 C16 C15 118.14(9) . . ?
C17 C16 C20 121.68(10) . . ?
C15 C16 C20 120.14(10) . . ?
C16 C17 C18 121.28(9) . . ?
C16 C17 H17 119.4 . . ?
C18 C17 H17 119.4 . . ?
C17 C18 C13 119.67(9) . . ?
C17 C18 C12 122.12(9) . . ?
C13 C18 C12 117.94(9) . . ?
C4 C19 H19A 109.5 . . ?
C4 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C4 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C16 C20 H20A 109.5 . . ?
C16 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C16 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C14 C21 H21A 109.5 . . ?
C14 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C14 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C2 C22 H22A 109.5 . . ?
C2 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C2 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C13 O3 V 125.48(7) . . ?

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 V O1 C1 -79.09(10) . . . . ?
O3 V O1 C1 172.93(9) . . . . ?
N2 V O1 C1 94.86(10) . . . . ?
N1 V O1 C1 20.74(9) . . . . ?
V O1 C1 C6 -35.98(14) . . . . ?
V O1 C1 C2 148.49(8) . . . . ?
O1 C1 C2 C3 177.67(9) . . . . ?
C6 C1 C2 C3 2.07(14) . . . . ?
O1 C1 C2 C22 0.26(14) . . . . ?
C6 C1 C2 C22 -175.34(9) . . . . ?
C1 C2 C3 C4 0.68(15) . . . . ?
C22 C2 C3 C4 178.01(10) . . . . ?
C2 C3 C4 C5 -2.02(16) . . . . ?
C2 C3 C4 C19 179.43(10) . . . . ?
C3 C4 C5 C6 0.60(15) . . . . ?
C19 C4 C5 C6 179.15(10) . . . . ?
C4 C5 C6 C1 2.12(15) . . . . ?
C4 C5 C6 C7 -172.27(9) . . . . ?
O1 C1 C6 C5 -178.99(9) . . . . ?
C2 C1 C6 C5 -3.46(14) . . . . ?
O1 C1 C6 C7 -4.44(14) . . . . ?
C2 C1 C6 C7 171.08(9) . . . . ?
C5 C6 C7 N1 -127.84(10) . . . . ?
C1 C6 C7 N1 57.66(12) . . . . ?
C6 C7 N1 C9 176.95(7) . . . . ?
C6 C7 N1 C8 58.30(10) . . . . ?
C6 C7 N1 V -64.34(9) . . . . ?
C8 N1 C9 C10 -153.74(8) . . . . ?
C7 N1 C9 C10 87.57(10) . . . . ?
V N1 C9 C10 -31.99(9) . . . . ?
N1 C9 C10 N2 56.20(10) . . . . ?
C9 C10 N2 C11 69.87(10) . . . . ?
C9 C10 N2 C12 -172.48(8) . . . . ?
C9 C10 N2 V -49.69(9) . . . . ?
C11 N2 C12 C18 -70.27(10) . . . . ?
C10 N2 C12 C18 170.54(8) . . . . ?
V N2 C12 C18 54.11(10) . . . . ?
O3 C13 C14 C15 -175.01(9) . . . . ?
C18 C13 C14 C15 1.51(14) . . . . ?
O3 C13 C14 C21 3.53(14) . . . . ?
C18 C13 C14 C21 -179.95(9) . . . . ?
C13 C14 C15 C16 -0.89(15) . . . . ?
C21 C14 C15 C16 -179.38(10) . . . . ?
C14 C15 C16 C17 -0.19(15) . . . . ?
C14 C15 C16 C20 177.42(10) . . . . ?
C15 C16 C17 C18 0.68(15) . . . . ?
C20 C16 C17 C18 -176.89(10) . . . . ?
C16 C17 C18 C13 -0.07(15) . . . . ?
C16 C17 C18 C12 173.77(10) . . . . ?
O3 C13 C18 C17 175.43(9) . . . . ?
C14 C13 C18 C17 -1.04(15) . . . . ?
O3 C13 C18 C12 1.33(14) . . . . ?
C14 C13 C18 C12 -175.14(9) . . . . ?
N2 C12 C18 C17 130.66(10) . . . . ?
N2 C12 C18 C13 -55.40(12) . . . . ?
C18 C13 O3 V 52.52(12) . . . . ?
C14 C13 O3 V -130.99(8) . . . . ?

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
C10 H10A O2 0.99 2.35 3.3018(16) 161.2 2_646
C12 H12B O1 0.99 2.38 3.1366(18) 132.8 3_666

_refine_diff_density_max         1.046
_refine_diff_density_min         -0.985
_refine_diff_density_rms         0.101

_shelxl_version_number           2013-2



####################################################################### 
# 
# 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 1997041'
loop_
_audit_author_name
_audit_author_address
'Marta S. Krawczyk '
;Faculty of Pharmacy, Wroclaw Medical University
Poland
;
_audit_update_record             
;
2020-04-15 deposited with the CCDC.	2021-03-05 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C40 H52 N4 O6 V2, 2(C2 H3 N)'
_chemical_formula_sum            'C44 H58 N6 O6 V2'
_chemical_formula_weight         868.84

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
V V 0.3005 0.5294 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   13.687(4)
_cell_length_b                   11.336(5)
_cell_length_c                   13.947(4)
_cell_angle_alpha                90
_cell_angle_beta                 94.91(3)
_cell_angle_gamma                90
_cell_volume                     2156.0(13)
_cell_formula_units_Z            2
_cell_measurement_temperature    125(2)
_cell_measurement_reflns_used    2989
_cell_measurement_theta_min      2.8
_cell_measurement_theta_max      31

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            BLUE
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.338
_exptl_crystal_F_000             916
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.280
_exptl_crystal_size_mid          0.130
_exptl_crystal_size_min          0.080
_exptl_absorpt_coefficient_mu    0.487
_shelx_estimated_absorpt_T_min   0.876
_shelx_estimated_absorpt_T_max   0.962
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_correction_T_min  0.917
_exptl_absorpt_correction_T_max  0.967
_exptl_absorpt_process_details   
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.33.66 (release 28-04-2010 CrysAlis171 .NET)
(compiled Apr 28 2010,14:27:37)
Analytical numeric absorption correction using a multifaceted crystal
                        model based on expressions derived by R.C. Clark & J.S.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
;
_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      125(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_measurement_device_type  'Xcalibur, ccd camera Ruby'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            12067
_diffrn_reflns_av_unetI/netI     0.0872
_diffrn_reflns_av_R_equivalents  0.0433
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.825
_diffrn_reflns_theta_max         30.853
_diffrn_reflns_theta_full        25.500
_diffrn_measured_fraction_theta_max 0.892
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.892
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.892
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             6054
_reflns_number_gt                4159
_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 CCD; Oxford-Diffraction Poland, 2003'
_computing_cell_refinement       'CrysAlis RED; Oxford-Diffraction Poland, 2003'
_computing_data_reduction        'CrysAlis RED; Oxford-Diffraction Poland, 2003'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_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)+(0.0332P)²+0.7224P]
 where P=(Fo²+2Fc²)/3
;
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         6054
_refine_ls_number_parameters     267
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0969
_refine_ls_R_factor_gt           0.0568
_refine_ls_wR_factor_ref         0.1124
_refine_ls_wR_factor_gt          0.0978
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_restrained_S_all      1.032
_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 0.54347(3) 0.44949(4) 0.60401(2) 0.01403(10) Uani 1 1 d . . . . .
O1 O 0.66790(11) 0.49656(16) 0.66530(10) 0.0183(4) Uani 1 1 d . . . . .
O2 O 0.55708(11) 0.31072(16) 0.58392(10) 0.0201(4) Uani 1 1 d . . . . .
O3 O 0.41759(10) 0.47224(15) 0.51693(10) 0.0151(3) Uani 1 1 d . . . . .
C1 C 0.71036(16) 0.4864(2) 0.75533(15) 0.0177(5) Uani 1 1 d . . . . .
C2 C 0.79832(16) 0.5455(2) 0.78035(16) 0.0216(5) Uani 1 1 d . . . . .
H2 H 0.8284 0.5894 0.7328 0.026 Uiso 1 1 calc R U . . .
C3 C 0.84261(18) 0.5410(3) 0.87370(17) 0.0263(6) Uani 1 1 d . . . . .
H3 H 0.9030 0.5810 0.8888 0.032 Uiso 1 1 calc R U . . .
C4 C 0.80006(19) 0.4792(3) 0.94514(17) 0.0276(6) Uani 1 1 d . . . . .
C5 C 0.71311(18) 0.4199(2) 0.91968(16) 0.0233(6) Uani 1 1 d . . . . .
H5 H 0.6831 0.3772 0.9679 0.028 Uiso 1 1 calc R U . . .
C6 C 0.66776(16) 0.4205(2) 0.82608(15) 0.0181(5) Uani 1 1 d . . . . .
C7 C 0.57973(16) 0.3445(2) 0.80129(15) 0.0193(5) Uani 1 1 d . . . . .
H7A H 0.5576 0.3126 0.8619 0.023 Uiso 1 1 calc R U . . .
H7B H 0.6003 0.2766 0.7631 0.023 Uiso 1 1 calc R U . . .
N1 N 0.49319(13) 0.40266(19) 0.74605(12) 0.0176(4) Uani 1 1 d . . . . .
C8 C 0.41572(17) 0.3106(2) 0.73697(16) 0.0228(5) Uani 1 1 d . . . . .
H8A H 0.3990 0.2872 0.8012 0.034 Uiso 1 1 calc R U . . .
H8B H 0.4398 0.2418 0.7036 0.034 Uiso 1 1 calc R U . . .
H8C H 0.3573 0.3421 0.7001 0.034 Uiso 1 1 calc R U . . .
C9 C 0.45640(17) 0.5041(2) 0.80159(15) 0.0197(5) Uani 1 1 d . . . . .
H9A H 0.4742 0.4916 0.8711 0.024 Uiso 1 1 calc R U . . .
H9B H 0.3840 0.5075 0.7912 0.024 Uiso 1 1 calc R U . . .
C10 C 0.49874(16) 0.6189(2) 0.77132(14) 0.0176(5) Uani 1 1 d . . . . .
H10A H 0.4661 0.6848 0.8025 0.021 Uiso 1 1 calc R U . . .
H10B H 0.5695 0.6216 0.7931 0.021 Uiso 1 1 calc R U . . .
N2 N 0.48597(13) 0.63402(18) 0.66533(12) 0.0151(4) Uani 1 1 d . . . . .
C11 C 0.54979(17) 0.7325(2) 0.63891(16) 0.0198(5) Uani 1 1 d . . . . .
H11A H 0.5308 0.8049 0.6708 0.030 Uiso 1 1 calc R U . . .
H11B H 0.5424 0.7438 0.5690 0.030 Uiso 1 1 calc R U . . .
H11C H 0.6183 0.7137 0.6595 0.030 Uiso 1 1 calc R U . . .
C12 C 0.38218(16) 0.6672(2) 0.63340(15) 0.0175(5) Uani 1 1 d . . . . .
H12A H 0.3826 0.7126 0.5728 0.021 Uiso 1 1 calc R U . . .
H12B H 0.3582 0.7206 0.6824 0.021 Uiso 1 1 calc R U . . .
C13 C 0.32743(16) 0.4778(2) 0.55230(14) 0.0146(5) Uani 1 1 d . . . . .
C14 C 0.25624(16) 0.3933(2) 0.52663(15) 0.0174(5) Uani 1 1 d . . . . .
H14 H 0.2692 0.3320 0.4830 0.021 Uiso 1 1 calc R U . . .
C15 C 0.16607(17) 0.3990(2) 0.56521(16) 0.0218(5) Uani 1 1 d . . . . .
H15 H 0.1170 0.3424 0.5464 0.026 Uiso 1 1 calc R U . . .
C16 C 0.14643(17) 0.4867(2) 0.63114(16) 0.0205(5) Uani 1 1 d . . . . .
C17 C 0.21928(16) 0.5691(2) 0.65592(15) 0.0193(5) Uani 1 1 d . . . . .
H17 H 0.2071 0.6287 0.7013 0.023 Uiso 1 1 calc R U . . .
C18 C 0.30954(15) 0.5679(2) 0.61680(14) 0.0151(5) Uani 1 1 d . . . . .
C19 C 0.8472(2) 0.4757(3) 1.04760(18) 0.0426(8) Uani 1 1 d . . . . .
H19A H 0.8010 0.5061 1.0915 0.064 Uiso 1 1 calc R U . . .
H19B H 0.9065 0.5246 1.0524 0.064 Uiso 1 1 calc R U . . .
H19C H 0.8647 0.3942 1.0650 0.064 Uiso 1 1 calc R U . . .
C20 C 0.04729(18) 0.4945(3) 0.67097(19) 0.0303(6) Uani 1 1 d . . . . .
H20A H 0.0562 0.5090 0.7404 0.045 Uiso 1 1 calc R U . . .
H20B H 0.0118 0.4202 0.6588 0.045 Uiso 1 1 calc R U . . .
H20C H 0.0096 0.5594 0.6395 0.045 Uiso 1 1 calc R U . . .
N1X N 0.06105(19) 0.7952(3) 0.50288(15) 0.0470(8) Uani 1 1 d . . . . .
C1X C 0.1192(2) 0.7509(3) 0.46239(16) 0.0278(6) Uani 1 1 d . . . . .
C2X C 0.19187(18) 0.6928(3) 0.40829(17) 0.0294(6) Uani 1 1 d . . . . .
H22A H 0.1964 0.6093 0.4264 0.044 Uiso 1 1 calc R U . . .
H22B H 0.2558 0.7306 0.4228 0.044 Uiso 1 1 calc R U . . .
H22C H 0.1723 0.6994 0.3392 0.044 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 O2 1.6115(19) . ?
V1 O1 1.9148(16) . ?
V1 O3 2.0174(16) 3_666 ?
V1 O3 2.0377(16) . ?
V1 N1 2.2166(19) . ?
V1 N2 2.417(2) . ?
O1 C1 1.343(2) . ?
O3 C13 1.369(3) . ?
O3 V1 2.0175(16) 3_666 ?
C1 C2 1.396(3) . ?
C1 C6 1.404(3) . ?
C2 C3 1.389(3) . ?
C2 H2 0.9500 . ?
C3 C4 1.387(4) . ?
C3 H3 0.9500 . ?
C4 C5 1.386(4) . ?
C4 C19 1.517(3) . ?
C5 C6 1.397(3) . ?
C5 H5 0.9500 . ?
C6 C7 1.498(3) . ?
C7 N1 1.508(3) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
N1 C8 1.485(3) . ?
N1 C9 1.498(3) . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C9 C10 1.500(3) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 N2 1.484(3) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
N2 C11 1.483(3) . ?
N2 C12 1.500(3) . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 C18 1.506(3) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 C14 1.391(3) . ?
C13 C18 1.396(3) . ?
C14 C15 1.389(3) . ?
C14 H14 0.9500 . ?
C15 C16 1.396(4) . ?
C15 H15 0.9500 . ?
C16 C17 1.389(3) . ?
C16 C20 1.512(3) . ?
C17 C18 1.393(3) . ?
C17 H17 0.9500 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
N1X C1X 1.132(3) . ?
C1X C2X 1.457(4) . ?
C2X H22A 0.9800 . ?
C2X H22B 0.9800 . ?
C2X H22C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O2 V1 O1 103.77(8) . . ?
O2 V1 O3 103.96(7) . 3_666 ?
O1 V1 O3 87.83(7) . 3_666 ?
O2 V1 O3 97.14(7) . . ?
O1 V1 O3 154.84(7) . . ?
O3 V1 O3 73.52(7) 3_666 . ?
O2 V1 N1 88.34(8) . . ?
O1 V1 N1 90.01(7) . . ?
O3 V1 N1 167.68(7) 3_666 . ?
O3 V1 N1 104.58(7) . . ?
O2 V1 N2 162.25(7) . . ?
O1 V1 N2 84.55(7) . . ?
O3 V1 N2 91.86(7) 3_666 . ?
O3 V1 N2 79.46(6) . . ?
N1 V1 N2 75.86(7) . . ?
C1 O1 V1 133.70(15) . . ?
C13 O3 V1 126.28(13) . 3_666 ?
C13 O3 V1 122.23(12) . . ?
V1 O3 V1 106.48(7) 3_666 . ?
O1 C1 C2 119.2(2) . . ?
O1 C1 C6 122.0(2) . . ?
C2 C1 C6 118.8(2) . . ?
C3 C2 C1 121.0(2) . . ?
C3 C2 H2 119.5 . . ?
C1 C2 H2 119.5 . . ?
C4 C3 C2 121.0(2) . . ?
C4 C3 H3 119.5 . . ?
C2 C3 H3 119.5 . . ?
C5 C4 C3 117.7(2) . . ?
C5 C4 C19 121.0(2) . . ?
C3 C4 C19 121.2(2) . . ?
C4 C5 C6 122.7(2) . . ?
C4 C5 H5 118.6 . . ?
C6 C5 H5 118.6 . . ?
C5 C6 C1 118.8(2) . . ?
C5 C6 C7 119.8(2) . . ?
C1 C6 C7 121.23(19) . . ?
C6 C7 N1 116.6(2) . . ?
C6 C7 H7A 108.1 . . ?
N1 C7 H7A 108.1 . . ?
C6 C7 H7B 108.1 . . ?
N1 C7 H7B 108.1 . . ?
H7A C7 H7B 107.3 . . ?
C8 N1 C9 108.32(18) . . ?
C8 N1 C7 105.07(19) . . ?
C9 N1 C7 110.83(17) . . ?
C8 N1 V1 111.48(13) . . ?
C9 N1 V1 114.97(15) . . ?
C7 N1 V1 105.72(13) . . ?
N1 C8 H8A 109.5 . . ?
N1 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
N1 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
N1 C9 C10 111.45(18) . . ?
N1 C9 H9A 109.3 . . ?
C10 C9 H9A 109.3 . . ?
N1 C9 H9B 109.3 . . ?
C10 C9 H9B 109.3 . . ?
H9A C9 H9B 108.0 . . ?
N2 C10 C9 111.41(18) . . ?
N2 C10 H10A 109.3 . . ?
C9 C10 H10A 109.3 . . ?
N2 C10 H10B 109.3 . . ?
C9 C10 H10B 109.3 . . ?
H10A C10 H10B 108.0 . . ?
C11 N2 C10 108.22(17) . . ?
C11 N2 C12 107.51(18) . . ?
C10 N2 C12 110.64(16) . . ?
C11 N2 V1 110.29(13) . . ?
C10 N2 V1 103.81(14) . . ?
C12 N2 V1 116.14(14) . . ?
N2 C11 H11A 109.5 . . ?
N2 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
N2 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
N2 C12 C18 117.0(2) . . ?
N2 C12 H12A 108.0 . . ?
C18 C12 H12A 108.0 . . ?
N2 C12 H12B 108.0 . . ?
C18 C12 H12B 108.0 . . ?
H12A C12 H12B 107.3 . . ?
O3 C13 C14 120.6(2) . . ?
O3 C13 C18 118.6(2) . . ?
C14 C13 C18 120.8(2) . . ?
C15 C14 C13 119.6(2) . . ?
C15 C14 H14 120.2 . . ?
C13 C14 H14 120.2 . . ?
C14 C15 C16 121.1(2) . . ?
C14 C15 H15 119.5 . . ?
C16 C15 H15 119.5 . . ?
C17 C16 C15 117.9(2) . . ?
C17 C16 C20 121.1(2) . . ?
C15 C16 C20 120.9(2) . . ?
C16 C17 C18 122.5(2) . . ?
C16 C17 H17 118.7 . . ?
C18 C17 H17 118.7 . . ?
C17 C18 C13 118.0(2) . . ?
C17 C18 C12 121.9(2) . . ?
C13 C18 C12 119.71(19) . . ?
C4 C19 H19A 109.5 . . ?
C4 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C4 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C16 C20 H20A 109.5 . . ?
C16 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C16 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
N1X C1X C2X 178.4(3) . . ?
C1X C2X H22A 109.5 . . ?
C1X C2X H22B 109.5 . . ?
H22A C2X H22B 109.5 . . ?
C1X C2X H22C 109.5 . . ?
H22A C2X H22C 109.5 . . ?
H22B C2X H22C 109.5 . . ?

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
V1 O1 C1 C2 -171.11(17) . . . . ?
V1 O1 C1 C6 7.2(4) . . . . ?
O1 C1 C2 C3 177.5(2) . . . . ?
C6 C1 C2 C3 -0.9(4) . . . . ?
C1 C2 C3 C4 -0.9(4) . . . . ?
C2 C3 C4 C5 1.4(4) . . . . ?
C2 C3 C4 C19 -179.0(3) . . . . ?
C3 C4 C5 C6 0.0(4) . . . . ?
C19 C4 C5 C6 -179.7(3) . . . . ?
C4 C5 C6 C1 -1.8(4) . . . . ?
C4 C5 C6 C7 173.6(2) . . . . ?
O1 C1 C6 C5 -176.1(2) . . . . ?
C2 C1 C6 C5 2.3(4) . . . . ?
O1 C1 C6 C7 8.5(4) . . . . ?
C2 C1 C6 C7 -173.1(2) . . . . ?
C5 C6 C7 N1 132.4(2) . . . . ?
C1 C6 C7 N1 -52.2(3) . . . . ?
C6 C7 N1 C8 -176.55(19) . . . . ?
C6 C7 N1 C9 -59.8(2) . . . . ?
C6 C7 N1 V1 65.4(2) . . . . ?
C8 N1 C9 C10 -149.44(18) . . . . ?
C7 N1 C9 C10 95.8(2) . . . . ?
V1 N1 C9 C10 -24.0(2) . . . . ?
N1 C9 C10 N2 51.1(2) . . . . ?
C9 C10 N2 C11 -166.18(19) . . . . ?
C9 C10 N2 C12 76.3(2) . . . . ?
C9 C10 N2 V1 -48.99(19) . . . . ?
C11 N2 C12 C18 157.06(18) . . . . ?
C10 N2 C12 C18 -85.0(2) . . . . ?
V1 N2 C12 C18 33.0(2) . . . . ?
V1 O3 C13 C14 91.3(2) 3_666 . . . ?
V1 O3 C13 C14 -117.19(19) . . . . ?
V1 O3 C13 C18 -90.6(2) 3_666 . . . ?
V1 O3 C13 C18 60.9(3) . . . . ?
O3 C13 C14 C15 178.5(2) . . . . ?
C18 C13 C14 C15 0.4(3) . . . . ?
C13 C14 C15 C16 -1.5(4) . . . . ?
C14 C15 C16 C17 1.0(4) . . . . ?
C14 C15 C16 C20 178.4(2) . . . . ?
C15 C16 C17 C18 0.7(3) . . . . ?
C20 C16 C17 C18 -176.7(2) . . . . ?
C16 C17 C18 C13 -1.8(3) . . . . ?
C16 C17 C18 C12 171.2(2) . . . . ?
O3 C13 C18 C17 -176.87(19) . . . . ?
C14 C13 C18 C17 1.2(3) . . . . ?
O3 C13 C18 C12 10.0(3) . . . . ?
C14 C13 C18 C12 -172.0(2) . . . . ?
N2 C12 C18 C17 130.9(2) . . . . ?
N2 C12 C18 C13 -56.2(3) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C7 H7A N1X 0.99 2.60 3.519(3) 154.5 2_546
C7 H7B O2 0.99 2.55 3.045(3) 110.9 .
C11 H11B O2 0.98 2.51 3.356(3) 144.7 3_666
C11 H11C O1 0.98 2.55 3.130(3) 117.6 .
C12 H12A O2 0.99 2.42 3.221(3) 137.9 3_666

_refine_diff_density_max         0.375
_refine_diff_density_min         -0.468
_refine_diff_density_rms         0.078

_shelxl_version_number           2013-2



####################################################################### 
# 
# 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 1997042'
loop_
_audit_author_name
_audit_author_address
'Marta S. Krawczyk '
;Faculty of Pharmacy, Wroclaw Medical University
Poland
;
_audit_update_record             
;
2020-04-15 deposited with the CCDC.	2021-03-05 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C36 H40 Cl4 N4 O6 V2, 2(C2 H3 N)'
_chemical_formula_sum            'C40 H46 Cl4 N6 O6 V2'
_chemical_formula_weight         950.51

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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
V V 0.3005 0.5294 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   13.557(4)
_cell_length_b                   11.269(3)
_cell_length_c                   13.829(5)
_cell_angle_alpha                90
_cell_angle_beta                 94.93(3)
_cell_angle_gamma                90
_cell_volume                     2104.9(11)
_cell_formula_units_Z            2
_cell_measurement_temperature    90(2)
_cell_measurement_reflns_used    3042
_cell_measurement_theta_min      2
_cell_measurement_theta_max      31

_exptl_crystal_description       block
_exptl_crystal_colour            dark-violet
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.500
_exptl_crystal_F_000             980
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.430
_exptl_crystal_size_mid          0.270
_exptl_crystal_size_min          0.180
_exptl_absorpt_coefficient_mu    0.752
_shelx_estimated_absorpt_T_min   0.738
_shelx_estimated_absorpt_T_max   0.877
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_correction_T_min  0.835
_exptl_absorpt_correction_T_max  0.921
_exptl_absorpt_process_details   
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.32.5
Analytical numeric absorption correction using a
multifaceted crystal model based on expressions
derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
;
_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      90(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_measurement_device_type  
;
Xcalibur R kappa-geometry diffractometer with a Ruby CCD detector
;
_diffrn_measurement_method       w/
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            10198
_diffrn_reflns_av_unetI/netI     0.0666
_diffrn_reflns_av_R_equivalents  0.0330
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         2.848
_diffrn_reflns_theta_max         30.628
_diffrn_reflns_theta_full        25.500
_diffrn_measured_fraction_theta_max 0.890
_diffrn_measured_fraction_theta_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.890
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.890
_diffrn_reflns_point_group_measured_fraction_full 0.989
_reflns_number_total             5777
_reflns_number_gt                4290
_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 PRO (Agilent, 2011)'
_computing_cell_refinement       'CrysAlis PRO (Agilent, 2011)'
_computing_data_reduction        'CrysAlis PRO (Agilent, 2011)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_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)+(0.0396P)²+0.2535P]
 where P=(Fo²+2Fc²)/3
;
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5777
_refine_ls_number_parameters     265
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0712
_refine_ls_R_factor_gt           0.0462
_refine_ls_wR_factor_ref         0.1071
_refine_ls_wR_factor_gt          0.0940
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_restrained_S_all      1.026
_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 0.54349(3) 0.45307(3) 0.60650(3) 0.01360(10) Uani 1 1 d . . . . .
Cl2 Cl 0.03005(4) 0.49061(5) 0.67781(5) 0.02628(14) Uani 1 1 d . . . . .
Cl1 Cl 0.85067(5) 0.48005(6) 1.07151(5) 0.03603(17) Uani 1 1 d . . . . .
O3 O 0.41632(11) 0.47000(12) 0.51638(11) 0.0139(3) Uani 1 1 d . . . . .
O2 O 0.56029(11) 0.31358(13) 0.58849(11) 0.0184(3) Uani 1 1 d . . . . .
O1 O 0.66855(11) 0.50315(13) 0.67023(11) 0.0173(3) Uani 1 1 d . . . . .
C1 C 0.70993(16) 0.49213(18) 0.76073(16) 0.0164(4) Uani 1 1 d . . . . .
C2 C 0.80041(17) 0.55006(19) 0.78720(17) 0.0196(5) Uani 1 1 d . . . . .
H2 H 0.8320 0.5931 0.7395 0.024 Uiso 1 1 calc R U . . .
C3 C 0.84436(18) 0.5456(2) 0.88178(18) 0.0236(5) Uani 1 1 d . . . . .
H3 H 0.9056 0.5845 0.8985 0.028 Uiso 1 1 calc R U . . .
C4 C 0.79778(18) 0.4837(2) 0.95118(18) 0.0230(5) Uani 1 1 d . . . . .
C5 C 0.70965(18) 0.42422(19) 0.92716(17) 0.0211(5) Uani 1 1 d . . . . .
H5 H 0.6788 0.3822 0.9759 0.025 Uiso 1 1 calc R U . . .
C6 C 0.66586(16) 0.42543(19) 0.83228(17) 0.0176(5) Uani 1 1 d . . . . .
C7 C 0.57694(16) 0.34919(19) 0.80613(16) 0.0175(5) Uani 1 1 d . . . . .
H7A H 0.5534 0.3179 0.8669 0.021 Uiso 1 1 calc R U . . .
H7B H 0.5982 0.2804 0.7685 0.021 Uiso 1 1 calc R U . . .
N1 N 0.49067(13) 0.40737(15) 0.74865(13) 0.0154(4) Uani 1 1 d . . . . .
C8 C 0.41207(16) 0.3146(2) 0.73951(17) 0.0205(5) Uani 1 1 d . . . . .
H8A H 0.3967 0.2894 0.8043 0.031 Uiso 1 1 calc R U . . .
H8B H 0.4355 0.2463 0.7041 0.031 Uiso 1 1 calc R U . . .
H8C H 0.3524 0.3472 0.7041 0.031 Uiso 1 1 calc R U . . .
C9 C 0.45302(16) 0.51061(19) 0.80328(16) 0.0176(5) Uani 1 1 d . . . . .
H9A H 0.4711 0.4997 0.8736 0.021 Uiso 1 1 calc R U . . .
H9B H 0.3799 0.5137 0.7927 0.021 Uiso 1 1 calc R U . . .
C10 C 0.49595(16) 0.62573(18) 0.77052(16) 0.0174(5) Uani 1 1 d . . . . .
H10A H 0.4630 0.6929 0.8008 0.021 Uiso 1 1 calc R U . . .
H10B H 0.5674 0.6288 0.7924 0.021 Uiso 1 1 calc R U . . .
N2 N 0.48286(13) 0.63819(15) 0.66306(13) 0.0148(4) Uani 1 1 d . . . . .
C11 C 0.54665(16) 0.73828(18) 0.63560(17) 0.0187(5) Uani 1 1 d . . . . .
H11A H 0.5260 0.8115 0.6663 0.028 Uiso 1 1 calc R U . . .
H11B H 0.5401 0.7480 0.5649 0.028 Uiso 1 1 calc R U . . .
H11C H 0.6159 0.7212 0.6575 0.028 Uiso 1 1 calc R U . . .
C12 C 0.37811(16) 0.66990(19) 0.63028(16) 0.0164(4) Uani 1 1 d . . . . .
H12A H 0.3782 0.7148 0.5688 0.020 Uiso 1 1 calc R U . . .
H12B H 0.3532 0.7239 0.6791 0.020 Uiso 1 1 calc R U . . .
C13 C 0.32538(15) 0.47620(18) 0.55067(15) 0.0142(4) Uani 1 1 d . . . . .
C14 C 0.25360(15) 0.39046(18) 0.52496(16) 0.0162(4) Uani 1 1 d . . . . .
H14 H 0.2674 0.3288 0.4812 0.019 Uiso 1 1 calc R U . . .
C15 C 0.16222(17) 0.39489(19) 0.56297(17) 0.0193(5) Uani 1 1 d . . . . .
H15 H 0.1126 0.3377 0.5445 0.023 Uiso 1 1 calc R U . . .
C16 C 0.14441(16) 0.4842(2) 0.62840(17) 0.0184(5) Uani 1 1 d . . . . .
C17 C 0.21519(16) 0.56964(19) 0.65457(16) 0.0178(5) Uani 1 1 d . . . . .
H17 H 0.2018 0.6293 0.7002 0.021 Uiso 1 1 calc R U . . .
C18 C 0.30593(16) 0.56852(18) 0.61430(15) 0.0148(4) Uani 1 1 d . . . . .
N1X N 0.93708(18) 0.1981(2) 0.50001(16) 0.0353(6) Uani 1 1 d . . . . .
C1X C 0.88173(18) 0.2498(2) 0.54109(17) 0.0231(5) Uani 1 1 d . . . . .
C2X C 0.81338(17) 0.3154(2) 0.59662(17) 0.0241(5) Uani 1 1 d . . . . .
H2A H 0.7472 0.2804 0.5860 0.036 Uiso 1 1 calc R U . . .
H2B H 0.8110 0.3984 0.5754 0.036 Uiso 1 1 calc R U . . .
H2C H 0.8359 0.3116 0.6658 0.036 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 O2 1.6108(15) . ?
V1 O1 1.9268(16) . ?
V1 O3 2.0236(16) 3_666 ?
V1 O3 2.0476(16) . ?
V1 N1 2.210(2) . ?
V1 N2 2.3979(18) . ?
Cl2 C16 1.749(2) . ?
Cl1 C4 1.755(2) . ?
O3 C13 1.360(2) . ?
O3 V1 2.0236(16) 3_666 ?
O1 C1 1.333(3) . ?
C1 C2 1.410(3) . ?
C1 C6 1.415(3) . ?
C2 C3 1.391(3) . ?
C2 H2 0.9500 . ?
C3 C4 1.382(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.385(3) . ?
C5 C6 1.393(3) . ?
C5 H5 0.9500 . ?
C6 C7 1.499(3) . ?
C7 N1 1.507(3) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
N1 C8 1.490(3) . ?
N1 C9 1.500(3) . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C9 C10 1.507(3) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 N2 1.488(3) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
N2 C11 1.490(3) . ?
N2 C12 1.496(3) . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 C18 1.508(3) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 C14 1.395(3) . ?
C13 C18 1.402(3) . ?
C14 C15 1.388(3) . ?
C14 H14 0.9500 . ?
C15 C16 1.388(3) . ?
C15 H15 0.9500 . ?
C16 C17 1.386(3) . ?
C17 C18 1.393(3) . ?
C17 H17 0.9500 . ?
N1X C1X 1.139(3) . ?
C1X C2X 1.455(3) . ?
C2X H2A 0.9800 . ?
C2X H2B 0.9800 . ?
C2X H2C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O2 V1 O1 103.06(7) . . ?
O2 V1 O3 103.68(7) . 3_666 ?
O1 V1 O3 88.21(7) . 3_666 ?
O2 V1 O3 96.87(7) . . ?
O1 V1 O3 155.90(6) . . ?
O3 V1 O3 73.88(7) 3_666 . ?
O2 V1 N1 88.34(7) . . ?
O1 V1 N1 90.06(7) . . ?
O3 V1 N1 167.94(6) 3_666 . ?
O3 V1 N1 104.05(7) . . ?
O2 V1 N2 163.02(7) . . ?
O1 V1 N2 84.77(6) . . ?
O3 V1 N2 91.48(6) 3_666 . ?
O3 V1 N2 79.81(6) . . ?
N1 V1 N2 76.48(6) . . ?
C13 O3 V1 126.03(13) . 3_666 ?
C13 O3 V1 122.25(13) . . ?
V1 O3 V1 106.12(7) 3_666 . ?
C1 O1 V1 133.25(14) . . ?
O1 C1 C2 119.2(2) . . ?
O1 C1 C6 122.49(19) . . ?
C2 C1 C6 118.3(2) . . ?
C3 C2 C1 121.4(2) . . ?
C3 C2 H2 119.3 . . ?
C1 C2 H2 119.3 . . ?
C4 C3 C2 119.1(2) . . ?
C4 C3 H3 120.4 . . ?
C2 C3 H3 120.4 . . ?
C3 C4 C5 120.9(2) . . ?
C3 C4 Cl1 119.75(18) . . ?
C5 C4 Cl1 119.33(19) . . ?
C4 C5 C6 120.7(2) . . ?
C4 C5 H5 119.7 . . ?
C6 C5 H5 119.7 . . ?
C5 C6 C1 119.5(2) . . ?
C5 C6 C7 119.4(2) . . ?
C1 C6 C7 121.0(2) . . ?
C6 C7 N1 116.71(18) . . ?
C6 C7 H7A 108.1 . . ?
N1 C7 H7A 108.1 . . ?
C6 C7 H7B 108.1 . . ?
N1 C7 H7B 108.1 . . ?
H7A C7 H7B 107.3 . . ?
C8 N1 C9 108.35(17) . . ?
C8 N1 C7 104.87(16) . . ?
C9 N1 C7 110.73(17) . . ?
C8 N1 V1 111.84(13) . . ?
C9 N1 V1 114.68(13) . . ?
C7 N1 V1 105.93(13) . . ?
N1 C8 H8A 109.5 . . ?
N1 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
N1 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
N1 C9 C10 111.04(18) . . ?
N1 C9 H9A 109.4 . . ?
C10 C9 H9A 109.4 . . ?
N1 C9 H9B 109.4 . . ?
C10 C9 H9B 109.4 . . ?
H9A C9 H9B 108.0 . . ?
N2 C10 C9 111.44(17) . . ?
N2 C10 H10A 109.3 . . ?
C9 C10 H10A 109.3 . . ?
N2 C10 H10B 109.3 . . ?
C9 C10 H10B 109.3 . . ?
H10A C10 H10B 108.0 . . ?
C10 N2 C11 107.69(17) . . ?
C10 N2 C12 110.71(17) . . ?
C11 N2 C12 107.37(16) . . ?
C10 N2 V1 103.23(12) . . ?
C11 N2 V1 110.65(13) . . ?
C12 N2 V1 116.87(12) . . ?
N2 C11 H11A 109.5 . . ?
N2 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
N2 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
N2 C12 C18 116.77(17) . . ?
N2 C12 H12A 108.1 . . ?
C18 C12 H12A 108.1 . . ?
N2 C12 H12B 108.1 . . ?
C18 C12 H12B 108.1 . . ?
H12A C12 H12B 107.3 . . ?
O3 C13 C14 120.58(18) . . ?
O3 C13 C18 118.80(18) . . ?
C14 C13 C18 120.6(2) . . ?
C15 C14 C13 120.3(2) . . ?
C15 C14 H14 119.9 . . ?
C13 C14 H14 119.9 . . ?
C14 C15 C16 118.9(2) . . ?
C14 C15 H15 120.5 . . ?
C16 C15 H15 120.5 . . ?
C17 C16 C15 121.3(2) . . ?
C17 C16 Cl2 119.10(17) . . ?
C15 C16 Cl2 119.64(17) . . ?
C16 C17 C18 120.3(2) . . ?
C16 C17 H17 119.8 . . ?
C18 C17 H17 119.8 . . ?
C17 C18 C13 118.53(19) . . ?
C17 C18 C12 121.24(19) . . ?
C13 C18 C12 119.96(19) . . ?
N1X C1X C2X 178.0(3) . . ?
C1X C2X H2A 109.5 . . ?
C1X C2X H2B 109.5 . . ?
H2A C2X H2B 109.5 . . ?
C1X C2X H2C 109.5 . . ?
H2A C2X H2C 109.5 . . ?
H2B C2X H2C 109.5 . . ?

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
V1 O1 C1 C2 -173.67(15) . . . . ?
V1 O1 C1 C6 5.5(3) . . . . ?
O1 C1 C2 C3 177.2(2) . . . . ?
C6 C1 C2 C3 -2.0(3) . . . . ?
C1 C2 C3 C4 -0.5(3) . . . . ?
C2 C3 C4 C5 1.5(3) . . . . ?
C2 C3 C4 Cl1 -178.48(18) . . . . ?
C3 C4 C5 C6 0.0(3) . . . . ?
Cl1 C4 C5 C6 -179.98(17) . . . . ?
C4 C5 C6 C1 -2.6(3) . . . . ?
C4 C5 C6 C7 173.1(2) . . . . ?
O1 C1 C6 C5 -175.6(2) . . . . ?
C2 C1 C6 C5 3.5(3) . . . . ?
O1 C1 C6 C7 8.8(3) . . . . ?
C2 C1 C6 C7 -172.07(19) . . . . ?
C5 C6 C7 N1 132.9(2) . . . . ?
C1 C6 C7 N1 -51.5(3) . . . . ?
C6 C7 N1 C8 -176.18(19) . . . . ?
C6 C7 N1 C9 -59.5(2) . . . . ?
C6 C7 N1 V1 65.4(2) . . . . ?
C8 N1 C9 C10 -148.68(18) . . . . ?
C7 N1 C9 C10 96.8(2) . . . . ?
V1 N1 C9 C10 -23.0(2) . . . . ?
N1 C9 C10 N2 51.2(2) . . . . ?
C9 C10 N2 C11 -167.10(17) . . . . ?
C9 C10 N2 C12 75.8(2) . . . . ?
C9 C10 N2 V1 -50.02(19) . . . . ?
C10 N2 C12 C18 -85.6(2) . . . . ?
C11 N2 C12 C18 157.11(18) . . . . ?
V1 N2 C12 C18 32.2(2) . . . . ?
V1 O3 C13 C14 91.3(2) 3_666 . . . ?
V1 O3 C13 C14 -118.85(19) . . . . ?
V1 O3 C13 C18 -90.4(2) 3_666 . . . ?
V1 O3 C13 C18 59.5(2) . . . . ?
O3 C13 C14 C15 177.67(19) . . . . ?
C18 C13 C14 C15 -0.7(3) . . . . ?
C13 C14 C15 C16 -1.4(3) . . . . ?
C14 C15 C16 C17 1.3(3) . . . . ?
C14 C15 C16 Cl2 -179.53(17) . . . . ?
C15 C16 C17 C18 0.9(3) . . . . ?
Cl2 C16 C17 C18 -178.25(16) . . . . ?
C16 C17 C18 C13 -2.9(3) . . . . ?
C16 C17 C18 C12 171.1(2) . . . . ?
O3 C13 C18 C17 -175.51(18) . . . . ?
C14 C13 C18 C17 2.8(3) . . . . ?
O3 C13 C18 C12 10.4(3) . . . . ?
C14 C13 C18 C12 -171.26(19) . . . . ?
N2 C12 C18 C17 130.4(2) . . . . ?
N2 C12 C18 C13 -55.6(3) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C7 H7A N1X 0.99 2.53 3.456(3) 155.5 4_566
C7 H7B O2 0.99 2.53 3.026(3) 111.0 .
C8 H8B O2 0.98 2.54 3.020(3) 110.0 .
C11 H11B O2 0.98 2.52 3.358(3) 143.7 3_666
C12 H12A O2 0.99 2.42 3.212(3) 137.0 3_666

_refine_diff_density_max         0.440
_refine_diff_density_min         -0.407
_refine_diff_density_rms         0.084

_shelxl_version_number           2013-2



####################################################################### 
# 
# 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 1997040'
loop_
_audit_author_name
_audit_author_address
'Marta S. Krawczyk '
;Faculty of Pharmacy, Wroclaw Medical University
Poland
;
_audit_update_record             
;
2020-04-15 deposited with the CCDC.	2021-03-05 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C68 H108 N4 O6 V2'
_chemical_formula_sum            'C68 H108 N4 O6 V2'
_chemical_formula_weight         1179.46

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
V V 0.3005 0.5294 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   20.300(9)
_cell_length_b                   8.107(2)
_cell_length_c                   22.043(10)
_cell_angle_alpha                90
_cell_angle_beta                 112.25(5)
_cell_angle_gamma                90
_cell_volume                     3358(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    5247
_cell_measurement_theta_min      3
_cell_measurement_theta_max      27

_exptl_crystal_description       plate
_exptl_crystal_colour            violet
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.167
_exptl_crystal_F_000             1276
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.410
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.050
_exptl_absorpt_coefficient_mu    0.329
_shelx_estimated_absorpt_T_min   0.877
_shelx_estimated_absorpt_T_max   0.984
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_correction_T_min  0.916
_exptl_absorpt_correction_T_max  0.982
_exptl_absorpt_process_details   
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.33.66 (release 28-04-2010 CrysAlis171 .NET)
(compiled Apr 28 2010,14:27:37)
Analytical numeric absorption correction using a multifaceted crystal
                        model based on expressions derived by R.C. Clark & J.S.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
;
_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_measurement_device_type  'Kuma KM4 with ccd camera'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            26589
_diffrn_reflns_av_unetI/netI     0.1012
_diffrn_reflns_av_R_equivalents  0.1151
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_theta_min         3.019
_diffrn_reflns_theta_max         27.059
_diffrn_reflns_theta_full        25.500
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             7341
_reflns_number_gt                4533
_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 CCD; Oxford-Diffraction Poland, 2003'
_computing_cell_refinement       'CrysAlis RED; Oxford-Diffraction Poland, 2003'
_computing_data_reduction        'CrysAlis RED; Oxford-Diffraction Poland, 2003'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_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)+(0.0875P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         7341
_refine_ls_number_parameters     398
_refine_ls_number_restraints     21
_refine_ls_R_factor_all          0.1247
_refine_ls_R_factor_gt           0.0732
_refine_ls_wR_factor_ref         0.1961
_refine_ls_wR_factor_gt          0.1636
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_restrained_S_all      1.034
_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 0.42654(3) 0.52421(6) 0.51194(3) 0.02731(19) Uani 1 1 d . . . . .
O2 O 0.39375(11) 0.6911(3) 0.47289(12) 0.0348(6) Uani 1 1 d . . . . .
O1 O 0.34885(12) 0.3704(3) 0.48193(12) 0.0350(6) Uani 1 1 d . . . . .
O3 O 0.53138(10) 0.5922(2) 0.54587(10) 0.0268(5) Uani 1 1 d . . . . .
C1 C 0.29576(17) 0.3345(4) 0.50115(18) 0.0350(9) Uani 1 1 d . . . . .
C2 C 0.25890(19) 0.1847(4) 0.48238(19) 0.0412(9) Uani 1 1 d . . . . .
H2 H 0.2711 0.1103 0.4550 0.049 Uiso 1 1 calc R U . . .
C3 C 0.2046(2) 0.1447(5) 0.50370(19) 0.0456(10) Uani 1 1 d . . . . .
H3 H 0.1798 0.0437 0.4894 0.055 Uiso 1 1 calc R U . . .
C4 C 0.18467(19) 0.2461(5) 0.54518(19) 0.0434(10) Uani 1 1 d . . . . .
C5 C 0.22198(17) 0.3934(5) 0.56283(19) 0.0396(9) Uani 1 1 d . . . . .
H5 H 0.2104 0.4657 0.5912 0.048 Uiso 1 1 calc R U . . .
C6 C 0.27582(16) 0.4419(4) 0.54127(18) 0.0332(8) Uani 1 1 d . . . . .
C7 C 0.30895(16) 0.6070(4) 0.5585(2) 0.0379(9) Uani 1 1 d . . . . .
H7A H 0.2903 0.6601 0.5892 0.045 Uiso 1 1 calc R U . . .
H7B H 0.2936 0.6749 0.5182 0.045 Uiso 1 1 calc R U . . .
N1 N 0.38872(13) 0.6099(3) 0.58905(14) 0.0314(7) Uani 1 1 d . . . . .
C8 C 0.40896(18) 0.7866(4) 0.6059(2) 0.0382(9) Uani 1 1 d . . . . .
H8A H 0.3910 0.8236 0.6391 0.057 Uiso 1 1 calc R U . . .
H8B H 0.3883 0.8548 0.5665 0.057 Uiso 1 1 calc R U . . .
H8C H 0.4609 0.7971 0.6232 0.057 Uiso 1 1 calc R U . . .
C9 C 0.41542(19) 0.5120(4) 0.65116(18) 0.0389(9) Uani 1 1 d . . . . .
H9A H 0.3792 0.5130 0.6712 0.047 Uiso 1 1 calc R U . . .
H9B H 0.4592 0.5640 0.6825 0.047 Uiso 1 1 calc R U . . .
C10 C 0.43134(18) 0.3354(4) 0.63899(19) 0.0369(9) Uani 1 1 d . . . . .
H10A H 0.4547 0.2783 0.6815 0.044 Uiso 1 1 calc R U . . .
H10B H 0.3862 0.2773 0.6143 0.044 Uiso 1 1 calc R U . . .
N2 N 0.47806(14) 0.3287(3) 0.60163(14) 0.0302(7) Uani 1 1 d . . . . .
C11 C 0.47449(19) 0.1603(4) 0.57342(19) 0.0395(9) Uani 1 1 d . . . . .
H11A H 0.4902 0.0790 0.6089 0.059 Uiso 1 1 calc R U . . .
H11B H 0.5055 0.1551 0.5485 0.059 Uiso 1 1 calc R U . . .
H11C H 0.4254 0.1362 0.5442 0.059 Uiso 1 1 calc R U . . .
C12 C 0.55419(17) 0.3579(4) 0.64494(17) 0.0312(8) Uani 1 1 d . . . . .
H12A H 0.5845 0.3072 0.6239 0.037 Uiso 1 1 calc R U . . .
H12B H 0.5639 0.2990 0.6868 0.037 Uiso 1 1 calc R U . . .
C13 C 0.56863(15) 0.6431(4) 0.60901(16) 0.0259(7) Uani 1 1 d . . . . .
C14 C 0.59623(16) 0.8013(4) 0.62205(17) 0.0300(8) Uani 1 1 d . . . . .
H14 H 0.5903 0.8753 0.5870 0.036 Uiso 1 1 calc R U . . .
C15 C 0.63229(17) 0.8512(4) 0.68603(18) 0.0337(8) Uani 1 1 d . . . . .
H15 H 0.6517 0.9594 0.6941 0.040 Uiso 1 1 calc R U . . .
C16 C 0.64118(17) 0.7476(4) 0.73940(17) 0.0337(8) Uani 1 1 d . . . . .
C17 C 0.61303(17) 0.5899(4) 0.72437(17) 0.0340(8) Uani 1 1 d . . . . .
H17 H 0.6187 0.5160 0.7594 0.041 Uiso 1 1 calc R U . . .
C18 C 0.57700(16) 0.5348(4) 0.66059(17) 0.0286(7) Uani 1 1 d . . . . .
C19 C 0.1218(2) 0.2034(5) 0.5654(2) 0.0516(11) Uani 1 1 d . . . . .
C20 C 0.1156(2) 0.3259(6) 0.6159(3) 0.0690(15) Uani 1 1 d . . . . .
H20A H 0.1611 0.3320 0.6534 0.104 Uiso 1 1 calc R U . . .
H20B H 0.0783 0.2890 0.6309 0.104 Uiso 1 1 calc R U . . .
H20C H 0.1033 0.4352 0.5958 0.104 Uiso 1 1 calc R U . . .
C21 C 0.0533(2) 0.2194(8) 0.5034(3) 0.095(2) Uani 1 1 d . . . . .
H21A H 0.0516 0.3289 0.4841 0.142 Uiso 1 1 calc R U . . .
H21B H 0.0117 0.2047 0.5152 0.142 Uiso 1 1 calc R U . . .
H21C H 0.0530 0.1347 0.4716 0.142 Uiso 1 1 calc R U . . .
C22 C 0.1247(3) 0.0246(5) 0.5907(2) 0.0587(12) Uani 1 1 d . . . . .
H22A H 0.0769 0.0011 0.5910 0.070 Uiso 1 1 calc R U . . .
H22B H 0.1301 -0.0475 0.5566 0.070 Uiso 1 1 calc R U . . .
C23 C 0.1784(3) -0.0370(6) 0.6563(3) 0.0668(13) Uani 1 1 d . . . . .
C24 C 0.2548(3) 0.0119(7) 0.6674(3) 0.0790(16) Uani 1 1 d . . . . .
H24A H 0.2607 0.1311 0.6751 0.119 Uiso 1 1 calc R U . . .
H24B H 0.2649 -0.0169 0.6286 0.119 Uiso 1 1 calc R U . . .
H24C H 0.2878 -0.0470 0.7056 0.119 Uiso 1 1 calc R U . . .
C25 C 0.1606(3) 0.0178(8) 0.7145(3) 0.092(2) Uani 1 1 d . . . . .
H25A H 0.1735 0.1341 0.7241 0.138 Uiso 1 1 calc R U . . .
H25B H 0.1873 -0.0494 0.7529 0.138 Uiso 1 1 calc R U . . .
H25C H 0.1095 0.0041 0.7039 0.138 Uiso 1 1 calc R U . . .
C26 C 0.1717(4) -0.2270(7) 0.6525(4) 0.123(3) Uani 1 1 d . . . . .
H26A H 0.2082 -0.2758 0.6915 0.185 Uiso 1 1 calc R U . . .
H26B H 0.1783 -0.2663 0.6131 0.185 Uiso 1 1 calc R U . . .
H26C H 0.1244 -0.2593 0.6505 0.185 Uiso 1 1 calc R U . . .
C27 C 0.6839(2) 0.8052(5) 0.8094(2) 0.0420(10) Uani 0.913(4) 1 d D . P A 1
C28 C 0.7589(2) 0.8514(6) 0.8132(2) 0.0575(14) Uani 0.913(4) 1 d D . P A 1
H28A H 0.7790 0.7600 0.7966 0.086 Uiso 0.913(4) 1 d R U P A 1
H28B H 0.7896 0.8745 0.8588 0.086 Uiso 0.913(4) 1 d R U P A 1
H28C H 0.7557 0.9498 0.7864 0.086 Uiso 0.913(4) 1 d R U P A 1
C29 C 0.6932(3) 0.6678(6) 0.8597(2) 0.0698(17) Uani 0.913(4) 1 d D . P A 1
H29A H 0.6463 0.6275 0.8560 0.105 Uiso 0.913(4) 1 calc R U P A 1
H29B H 0.7188 0.7111 0.9039 0.105 Uiso 0.913(4) 1 calc R U P A 1
H29C H 0.7204 0.5769 0.8512 0.105 Uiso 0.913(4) 1 calc R U P A 1
C30 C 0.6530(2) 0.9648(5) 0.8277(2) 0.0440(11) Uani 0.913(4) 1 d D . P A 1
H30A H 0.6901 1.0065 0.8686 0.053 Uiso 0.913(4) 1 calc R U P A 1
H30B H 0.6493 1.0465 0.7932 0.053 Uiso 0.913(4) 1 calc R U P A 1
C31 C 0.5827(2) 0.9736(8) 0.8380(2) 0.0590(15) Uani 0.913(4) 1 d D . P A 1
C32 C 0.5891(3) 0.8978(9) 0.9042(3) 0.0823(19) Uani 0.913(4) 1 d D . P A 1
H32A H 0.5903 0.7775 0.9005 0.124 Uiso 0.913(4) 1 d R U P A 1
H32B H 0.5477 0.9298 0.9143 0.124 Uiso 0.913(4) 1 d R U P A 1
H32C H 0.6327 0.9356 0.9394 0.124 Uiso 0.913(4) 1 d R U P A 1
C33 C 0.5649(3) 1.1605(8) 0.8403(3) 0.0808(19) Uani 0.913(4) 1 d D . P A 1
H33A H 0.6029 1.2147 0.8766 0.121 Uiso 0.913(4) 1 d R U P A 1
H33B H 0.5198 1.1715 0.8465 0.121 Uiso 0.913(4) 1 d R U P A 1
H33C H 0.5605 1.2125 0.7988 0.121 Uiso 0.913(4) 1 d R U P A 1
C34 C 0.5206(2) 0.8947(9) 0.7816(3) 0.079(2) Uani 0.913(4) 1 d D . P A 1
H34A H 0.5214 0.9294 0.7393 0.118 Uiso 0.913(4) 1 d R U P A 1
H34B H 0.4750 0.9260 0.7839 0.118 Uiso 0.913(4) 1 d R U P A 1
H34C H 0.5264 0.7747 0.7859 0.118 Uiso 0.913(4) 1 d R U P A 1
C37 C 0.6970(10) 0.809(3) 0.8100(11) 0.0420(10) Uani 0.087(4) 1 d D . P A 2
C38 C 0.7240(16) 0.986(3) 0.8114(17) 0.025(8) Uiso 0.087(4) 1 d D . P A 2
H38A H 0.6840 1.0628 0.8011 0.037 Uiso 0.087(4) 1 calc R U P A 2
H38B H 0.7594 1.0103 0.8551 0.037 Uiso 0.087(4) 1 calc R U P A 2
H38C H 0.7459 0.9976 0.7789 0.037 Uiso 0.087(4) 1 calc R U P A 2
C39 C 0.7613(13) 0.694(3) 0.8263(16) 0.021(8) Uiso 0.087(4) 1 d D . P A 2
H39A H 0.7459 0.5797 0.8258 0.032 Uiso 0.087(4) 1 calc R U P A 2
H39B H 0.7828 0.7087 0.7936 0.032 Uiso 0.087(4) 1 calc R U P A 2
H39C H 0.7963 0.7215 0.8699 0.032 Uiso 0.087(4) 1 calc R U P A 2
C40 C 0.6633(11) 0.799(4) 0.8619(12) 0.046(12) Uiso 0.087(4) 1 d D . P A 2
H40A H 0.6661 0.6809 0.8743 0.055 Uiso 0.087(4) 1 calc R U P A 2
H40B H 0.6969 0.8573 0.9007 0.055 Uiso 0.087(4) 1 calc R U P A 2
C41 C 0.5896(9) 0.855(3) 0.8561(10) 0.046(12) Uiso 0.087(4) 1 d D . P A 2
C42 C 0.5752(15) 0.811(4) 0.9182(12) 0.030 Uiso 0.087(4) 1 d D U P A 2
H42A H 0.5275 0.8485 0.9130 0.045 Uiso 0.087(4) 1 calc R U P A 2
H42B H 0.5784 0.6911 0.9247 0.045 Uiso 0.087(4) 1 calc R U P A 2
H42C H 0.6106 0.8652 0.9564 0.045 Uiso 0.087(4) 1 calc R U P A 2
C43 C 0.5874(17) 1.047(3) 0.8508(18) 0.030 Uiso 0.087(4) 1 d D U P A 2
H43A H 0.5404 1.0868 0.8470 0.045 Uiso 0.087(4) 1 calc R U P A 2
H43B H 0.6239 1.0943 0.8901 0.045 Uiso 0.087(4) 1 calc R U P A 2
H43C H 0.5965 1.0807 0.8120 0.045 Uiso 0.087(4) 1 calc R U P A 2
C44 C 0.5295(12) 0.787(4) 0.7948(12) 0.030 Uiso 0.087(4) 1 d D U P A 2
H44A H 0.4836 0.8277 0.7939 0.045 Uiso 0.087(4) 1 calc R U P A 2
H44B H 0.5366 0.8252 0.7555 0.045 Uiso 0.087(4) 1 calc R U P A 2
H44C H 0.5301 0.6666 0.7961 0.045 Uiso 0.087(4) 1 calc R U P A 2


_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 O2 1.606(2) . ?
V1 O1 1.921(2) . ?
V1 O3 2.017(2) 3_666 ?
V1 O3 2.046(2) . ?
V1 N1 2.225(3) . ?
V1 N2 2.439(3) . ?
O1 C1 1.331(4) . ?
O3 C13 1.372(4) . ?
O3 V1 2.017(2) 3_666 ?
C1 C2 1.404(5) . ?
C1 C6 1.405(5) . ?
C2 C3 1.391(5) . ?
C2 H2 0.9500 . ?
C3 C4 1.398(6) . ?
C3 H3 0.9500 . ?
C4 C5 1.388(5) . ?
C4 C19 1.542(5) . ?
C5 C6 1.403(5) . ?
C5 H5 0.9500 . ?
C6 C7 1.481(4) . ?
C7 N1 1.500(4) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
N1 C9 1.496(5) . ?
N1 C8 1.498(4) . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C9 C10 1.514(5) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 N2 1.474(5) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
N2 C11 1.490(4) . ?
N2 C12 1.496(4) . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 C18 1.506(4) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 C14 1.385(4) . ?
C13 C18 1.395(5) . ?
C14 C15 1.381(5) . ?
C14 H14 0.9500 . ?
C15 C16 1.401(5) . ?
C15 H15 0.9500 . ?
C16 C17 1.388(5) . ?
C16 C27 1.529(5) . ?
C16 C37 1.62(2) . ?
C17 C18 1.390(5) . ?
C17 H17 0.9500 . ?
C19 C20 1.533(6) . ?
C19 C21 1.543(6) . ?
C19 C22 1.546(6) . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C22 C23 1.529(7) . ?
C22 H22A 0.9900 . ?
C22 H22B 0.9900 . ?
C23 C25 1.524(7) . ?
C23 C24 1.529(7) . ?
C23 C26 1.546(7) . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 0.9800 . ?
C25 H25A 0.9800 . ?
C25 H25B 0.9800 . ?
C25 H25C 0.9800 . ?
C26 H26A 0.9800 . ?
C26 H26B 0.9800 . ?
C26 H26C 0.9800 . ?
C27 C29 1.532(5) . ?
C27 C28 1.539(5) . ?
C27 C30 1.555(5) . ?
C28 H28A 0.9800 . ?
C28 H28B 0.9800 . ?
C28 H28C 0.9800 . ?
C29 H29A 0.9800 . ?
C29 H29B 0.9800 . ?
C29 H29C 0.9800 . ?
C30 C31 1.532(6) . ?
C30 H30A 0.9900 . ?
C30 H30B 0.9900 . ?
C31 C34 1.536(6) . ?
C31 C32 1.543(8) . ?
C31 C33 1.563(8) . ?
C32 H32A 0.9800 . ?
C32 H32B 0.9800 . ?
C32 H32C 0.9800 . ?
C33 H33A 0.9800 . ?
C33 H33B 0.9800 . ?
C33 H33C 0.9800 . ?
C34 H34A 0.9800 . ?
C34 H34B 0.9800 . ?
C34 H34C 0.9800 . ?
C37 C39 1.528(6) . ?
C37 C38 1.533(6) . ?
C37 C40 1.541(6) . ?
C38 H38A 0.9800 . ?
C38 H38B 0.9800 . ?
C38 H38C 0.9800 . ?
C39 H39A 0.9800 . ?
C39 H39B 0.9800 . ?
C39 H39C 0.9800 . ?
C40 C41 1.522(6) . ?
C40 H40A 0.9900 . ?
C40 H40B 0.9900 . ?
C41 C44 1.536(8) . ?
C41 C42 1.547(9) . ?
C41 C43 1.563(9) . ?
C42 H42A 0.9800 . ?
C42 H42B 0.9800 . ?
C42 H42C 0.9800 . ?
C43 H43A 0.9800 . ?
C43 H43B 0.9800 . ?
C43 H43C 0.9800 . ?
C44 H44A 0.9800 . ?
C44 H44B 0.9800 . ?
C44 H44C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O2 V1 O1 104.04(11) . . ?
O2 V1 O3 104.12(11) . 3_666 ?
O1 V1 O3 88.14(10) . 3_666 ?
O2 V1 O3 97.57(10) . . ?
O1 V1 O3 154.86(9) . . ?
O3 V1 O3 74.11(10) 3_666 . ?
O2 V1 N1 87.34(12) . . ?
O1 V1 N1 89.43(11) . . ?
O3 V1 N1 168.54(9) 3_666 . ?
O3 V1 N1 104.40(10) . . ?
O2 V1 N2 160.95(11) . . ?
O1 V1 N2 84.34(10) . . ?
O3 V1 N2 93.09(10) 3_666 . ?
O3 V1 N2 79.12(10) . . ?
N1 V1 N2 75.52(10) . . ?
C1 O1 V1 133.7(2) . . ?
C13 O3 V1 125.39(18) . 3_666 ?
C13 O3 V1 123.3(2) . . ?
V1 O3 V1 105.90(10) 3_666 . ?
O1 C1 C2 120.0(3) . . ?
O1 C1 C6 121.7(3) . . ?
C2 C1 C6 118.2(3) . . ?
C3 C2 C1 120.3(4) . . ?
C3 C2 H2 119.9 . . ?
C1 C2 H2 119.9 . . ?
C2 C3 C4 123.1(3) . . ?
C2 C3 H3 118.4 . . ?
C4 C3 H3 118.4 . . ?
C5 C4 C3 115.3(4) . . ?
C5 C4 C19 122.4(4) . . ?
C3 C4 C19 122.2(3) . . ?
C4 C5 C6 123.9(4) . . ?
C4 C5 H5 118.0 . . ?
C6 C5 H5 118.0 . . ?
C5 C6 C1 119.1(3) . . ?
C5 C6 C7 120.2(3) . . ?
C1 C6 C7 120.7(3) . . ?
C6 C7 N1 116.0(3) . . ?
C6 C7 H7A 108.3 . . ?
N1 C7 H7A 108.3 . . ?
C6 C7 H7B 108.3 . . ?
N1 C7 H7B 108.3 . . ?
H7A C7 H7B 107.4 . . ?
C9 N1 C8 108.1(3) . . ?
C9 N1 C7 111.0(3) . . ?
C8 N1 C7 105.9(2) . . ?
C9 N1 V1 115.0(2) . . ?
C8 N1 V1 110.3(2) . . ?
C7 N1 V1 106.2(2) . . ?
N1 C8 H8A 109.5 . . ?
N1 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
N1 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
N1 C9 C10 111.6(3) . . ?
N1 C9 H9A 109.3 . . ?
C10 C9 H9A 109.3 . . ?
N1 C9 H9B 109.3 . . ?
C10 C9 H9B 109.3 . . ?
H9A C9 H9B 108.0 . . ?
N2 C10 C9 111.1(3) . . ?
N2 C10 H10A 109.4 . . ?
C9 C10 H10A 109.4 . . ?
N2 C10 H10B 109.4 . . ?
C9 C10 H10B 109.4 . . ?
H10A C10 H10B 108.0 . . ?
C10 N2 C11 109.1(3) . . ?
C10 N2 C12 111.4(3) . . ?
C11 N2 C12 106.7(3) . . ?
C10 N2 V1 105.04(19) . . ?
C11 N2 V1 108.6(2) . . ?
C12 N2 V1 115.88(19) . . ?
N2 C11 H11A 109.5 . . ?
N2 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
N2 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
N2 C12 C18 116.8(3) . . ?
N2 C12 H12A 108.1 . . ?
C18 C12 H12A 108.1 . . ?
N2 C12 H12B 108.1 . . ?
C18 C12 H12B 108.1 . . ?
H12A C12 H12B 107.3 . . ?
O3 C13 C14 120.9(3) . . ?
O3 C13 C18 119.2(3) . . ?
C14 C13 C18 119.9(3) . . ?
C15 C14 C13 120.0(3) . . ?
C15 C14 H14 120.0 . . ?
C13 C14 H14 120.0 . . ?
C14 C15 C16 122.1(3) . . ?
C14 C15 H15 118.9 . . ?
C16 C15 H15 118.9 . . ?
C17 C16 C15 116.2(3) . . ?
C17 C16 C27 123.2(3) . . ?
C15 C16 C27 120.5(3) . . ?
C17 C16 C37 126.0(8) . . ?
C15 C16 C37 116.4(8) . . ?
C16 C17 C18 123.3(3) . . ?
C16 C17 H17 118.4 . . ?
C18 C17 H17 118.4 . . ?
C17 C18 C13 118.5(3) . . ?
C17 C18 C12 122.4(3) . . ?
C13 C18 C12 118.7(3) . . ?
C20 C19 C4 111.7(3) . . ?
C20 C19 C21 107.1(4) . . ?
C4 C19 C21 107.0(4) . . ?
C20 C19 C22 110.4(4) . . ?
C4 C19 C22 113.1(4) . . ?
C21 C19 C22 107.2(4) . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C19 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C19 C21 H21A 109.5 . . ?
C19 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C19 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C23 C22 C19 124.3(4) . . ?
C23 C22 H22A 106.3 . . ?
C19 C22 H22A 106.3 . . ?
C23 C22 H22B 106.3 . . ?
C19 C22 H22B 106.3 . . ?
H22A C22 H22B 106.4 . . ?
C25 C23 C22 112.9(4) . . ?
C25 C23 C24 109.8(5) . . ?
C22 C23 C24 112.6(4) . . ?
C25 C23 C26 107.0(5) . . ?
C22 C23 C26 104.9(5) . . ?
C24 C23 C26 109.3(5) . . ?
C23 C24 H24A 109.5 . . ?
C23 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
C23 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C23 C25 H25A 109.5 . . ?
C23 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
C23 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
C23 C26 H26A 109.5 . . ?
C23 C26 H26B 109.5 . . ?
H26A C26 H26B 109.5 . . ?
C23 C26 H26C 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
C16 C27 C29 112.0(3) . . ?
C16 C27 C28 107.5(3) . . ?
C29 C27 C28 106.8(4) . . ?
C16 C27 C30 112.7(3) . . ?
C29 C27 C30 111.6(4) . . ?
C28 C27 C30 105.7(3) . . ?
C27 C28 H28A 109.8 . . ?
C27 C28 H28B 109.5 . . ?
H28A C28 H28B 109.5 . . ?
C27 C28 H28C 109.1 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?
C27 C29 H29A 109.5 . . ?
C27 C29 H29B 109.5 . . ?
H29A C29 H29B 109.5 . . ?
C27 C29 H29C 109.5 . . ?
H29A C29 H29C 109.5 . . ?
H29B C29 H29C 109.5 . . ?
C31 C30 C27 124.6(4) . . ?
C31 C30 H30A 106.2 . . ?
C27 C30 H30A 106.2 . . ?
C31 C30 H30B 106.2 . . ?
C27 C30 H30B 106.2 . . ?
H30A C30 H30B 106.4 . . ?
C30 C31 C34 112.7(4) . . ?
C30 C31 C32 111.9(4) . . ?
C34 C31 C32 110.5(5) . . ?
C30 C31 C33 106.9(4) . . ?
C34 C31 C33 107.5(5) . . ?
C32 C31 C33 107.1(5) . . ?
C31 C32 H32A 108.3 . . ?
C31 C32 H32B 109.6 . . ?
H32A C32 H32B 109.5 . . ?
C31 C32 H32C 110.6 . . ?
H32A C32 H32C 109.5 . . ?
H32B C32 H32C 109.5 . . ?
C31 C33 H33A 109.9 . . ?
C31 C33 H33B 109.4 . . ?
H33A C33 H33B 109.5 . . ?
C31 C33 H33C 109.1 . . ?
H33A C33 H33C 109.5 . . ?
H33B C33 H33C 109.5 . . ?
C31 C34 H34A 110.3 . . ?
C31 C34 H34B 110.5 . . ?
H34A C34 H34B 109.5 . . ?
C31 C34 H34C 107.6 . . ?
H34A C34 H34C 109.5 . . ?
H34B C34 H34C 109.5 . . ?
C39 C37 C38 107.2(8) . . ?
C39 C37 C40 111.9(8) . . ?
C38 C37 C40 106.8(8) . . ?
C39 C37 C16 105.4(15) . . ?
C38 C37 C16 115.0(17) . . ?
C40 C37 C16 110.6(13) . . ?
C37 C38 H38A 109.5 . . ?
C37 C38 H38B 109.5 . . ?
H38A C38 H38B 109.5 . . ?
C37 C38 H38C 109.5 . . ?
H38A C38 H38C 109.5 . . ?
H38B C38 H38C 109.5 . . ?
C37 C39 H39A 109.5 . . ?
C37 C39 H39B 109.5 . . ?
H39A C39 H39B 109.5 . . ?
C37 C39 H39C 109.5 . . ?
H39A C39 H39C 109.5 . . ?
H39B C39 H39C 109.5 . . ?
C41 C40 C37 128.4(9) . . ?
C41 C40 H40A 105.2 . . ?
C37 C40 H40A 105.2 . . ?
C41 C40 H40B 105.2 . . ?
C37 C40 H40B 105.2 . . ?
H40A C40 H40B 105.9 . . ?
C40 C41 C44 113.3(8) . . ?
C40 C41 C42 111.5(7) . . ?
C44 C41 C42 110.1(8) . . ?
C40 C41 C43 107.6(8) . . ?
C44 C41 C43 107.4(8) . . ?
C42 C41 C43 106.6(8) . . ?
C41 C42 H42A 109.5 . . ?
C41 C42 H42B 109.5 . . ?
H42A C42 H42B 109.5 . . ?
C41 C42 H42C 109.5 . . ?
H42A C42 H42C 109.5 . . ?
H42B C42 H42C 109.5 . . ?
C41 C43 H43A 109.5 . . ?
C41 C43 H43B 109.5 . . ?
H43A C43 H43B 109.5 . . ?
C41 C43 H43C 109.5 . . ?
H43A C43 H43C 109.5 . . ?
H43B C43 H43C 109.5 . . ?
C41 C44 H44A 109.5 . . ?
C41 C44 H44B 109.5 . . ?
H44A C44 H44B 109.5 . . ?
C41 C44 H44C 109.5 . . ?
H44A C44 H44C 109.5 . . ?
H44B C44 H44C 109.5 . . ?

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
V1 O1 C1 C2 -161.5(2) . . . . ?
V1 O1 C1 C6 17.3(5) . . . . ?
O1 C1 C2 C3 178.4(3) . . . . ?
C6 C1 C2 C3 -0.5(5) . . . . ?
C1 C2 C3 C4 -1.5(6) . . . . ?
C2 C3 C4 C5 1.5(6) . . . . ?
C2 C3 C4 C19 176.9(4) . . . . ?
C3 C4 C5 C6 0.4(6) . . . . ?
C19 C4 C5 C6 -175.0(4) . . . . ?
C4 C5 C6 C1 -2.3(5) . . . . ?
C4 C5 C6 C7 175.3(3) . . . . ?
O1 C1 C6 C5 -176.6(3) . . . . ?
C2 C1 C6 C5 2.2(5) . . . . ?
O1 C1 C6 C7 5.9(5) . . . . ?
C2 C1 C6 C7 -175.3(3) . . . . ?
C5 C6 C7 N1 128.1(4) . . . . ?
C1 C6 C7 N1 -54.4(5) . . . . ?
C6 C7 N1 C9 -59.2(4) . . . . ?
C6 C7 N1 C8 -176.3(3) . . . . ?
C6 C7 N1 V1 66.4(4) . . . . ?
C8 N1 C9 C10 -151.6(3) . . . . ?
C7 N1 C9 C10 92.7(3) . . . . ?
V1 N1 C9 C10 -27.9(3) . . . . ?
N1 C9 C10 N2 51.7(4) . . . . ?
C9 C10 N2 C11 -162.9(3) . . . . ?
C9 C10 N2 C12 79.6(3) . . . . ?
C9 C10 N2 V1 -46.6(3) . . . . ?
C10 N2 C12 C18 -81.6(4) . . . . ?
C11 N2 C12 C18 159.4(3) . . . . ?
V1 N2 C12 C18 38.4(4) . . . . ?
V1 O3 C13 C14 92.6(3) 3_666 . . . ?
V1 O3 C13 C14 -117.0(3) . . . . ?
V1 O3 C13 C18 -89.0(3) 3_666 . . . ?
V1 O3 C13 C18 61.3(3) . . . . ?
O3 C13 C14 C15 178.7(3) . . . . ?
C18 C13 C14 C15 0.3(5) . . . . ?
C13 C14 C15 C16 -1.2(5) . . . . ?
C14 C15 C16 C17 1.4(5) . . . . ?
C14 C15 C16 C27 177.7(3) . . . . ?
C14 C15 C16 C37 168.5(8) . . . . ?
C15 C16 C17 C18 -0.8(5) . . . . ?
C27 C16 C17 C18 -176.9(3) . . . . ?
C37 C16 C17 C18 -166.5(8) . . . . ?
C16 C17 C18 C13 0.0(5) . . . . ?
C16 C17 C18 C12 172.9(3) . . . . ?
O3 C13 C18 C17 -178.1(3) . . . . ?
C14 C13 C18 C17 0.3(5) . . . . ?
O3 C13 C18 C12 8.8(4) . . . . ?
C14 C13 C18 C12 -172.9(3) . . . . ?
N2 C12 C18 C17 129.1(3) . . . . ?
N2 C12 C18 C13 -58.0(4) . . . . ?
C5 C4 C19 C20 -10.1(6) . . . . ?
C3 C4 C19 C20 174.8(4) . . . . ?
C5 C4 C19 C21 106.8(5) . . . . ?
C3 C4 C19 C21 -68.4(5) . . . . ?
C5 C4 C19 C22 -135.4(4) . . . . ?
C3 C4 C19 C22 49.5(5) . . . . ?
C20 C19 C22 C23 -54.9(6) . . . . ?
C4 C19 C22 C23 71.1(5) . . . . ?
C21 C19 C22 C23 -171.2(4) . . . . ?
C19 C22 C23 C25 76.5(6) . . . . ?
C19 C22 C23 C24 -48.6(6) . . . . ?
C19 C22 C23 C26 -167.3(4) . . . . ?
C17 C16 C27 C29 1.5(5) . . . . ?
C15 C16 C27 C29 -174.4(4) . . . . ?
C17 C16 C27 C28 118.6(4) . . . . ?
C15 C16 C27 C28 -57.4(5) . . . . ?
C17 C16 C27 C30 -125.4(4) . . . . ?
C15 C16 C27 C30 58.7(5) . . . . ?
C16 C27 C30 C31 70.1(5) . . . . ?
C29 C27 C30 C31 -57.1(5) . . . . ?
C28 C27 C30 C31 -172.8(4) . . . . ?
C27 C30 C31 C34 -50.0(7) . . . . ?
C27 C30 C31 C32 75.2(6) . . . . ?
C27 C30 C31 C33 -167.9(4) . . . . ?
C17 C16 C37 C39 57.4(12) . . . . ?
C15 C16 C37 C39 -108.3(10) . . . . ?
C17 C16 C37 C38 175.2(11) . . . . ?
C15 C16 C37 C38 9.6(14) . . . . ?
C17 C16 C37 C40 -63.7(12) . . . . ?
C15 C16 C37 C40 130.7(10) . . . . ?
C39 C37 C40 C41 -162(2) . . . . ?
C38 C37 C40 C41 80(2) . . . . ?
C16 C37 C40 C41 -45(2) . . . . ?
C37 C40 C41 C44 51(2) . . . . ?
C37 C40 C41 C42 176(2) . . . . ?
C37 C40 C41 C43 -67(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
C11 H11C O1 0.98 2.51 3.095(4) 118.3 .
C12 H12A O2 0.99 2.34 3.178(5) 142.3 3_666

_refine_diff_density_max         0.357
_refine_diff_density_min         -0.468
_refine_diff_density_rms         0.079



