# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2019

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_2
_database_code_depnum_ccdc_archive 'CCDC 1887600'
_audit_update_record             
;
2018-12-27 deposited with the CCDC.	2019-10-01 downloaded from the CCDC.
;




_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C28 H23 N5 O3 V'
_chemical_formula_weight         528.45

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      triclinic
_space_group_IT_number           1
_space_group_name_H-M_alt        'P 1'
_space_group_name_Hall           'P 1'

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

loop_
_space_group_symop_operation_xyz
'x, y, z'

_cell_length_a                   10.2716(10)
_cell_length_b                   10.6456(9)
_cell_length_c                   12.1344(9)
_cell_angle_alpha                81.817(7)
_cell_angle_beta                 70.266(8)
_cell_angle_gamma                82.082(7)
_cell_volume                     1230.48(19)
_cell_formula_units_Z            2
_cell_measurement_temperature    100.00(2)
_cell_measurement_reflns_used    2157
_cell_measurement_theta_min      1.9190
_cell_measurement_theta_max      25.0080

_exptl_crystal_description       block
_exptl_crystal_colour            red
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.426
_exptl_crystal_F_000             546
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.03
_exptl_absorpt_coefficient_mu    0.444
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.63839
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33c (release 11-04-2014 CrysAlis171 .NET)
(compiled Apr 11 2014,15:12:41)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100.00(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            7234
_diffrn_reflns_av_unetI/netI     0.1216
_diffrn_reflns_av_R_equivalents  0.0666
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         1.792
_diffrn_reflns_theta_max         25.016
_diffrn_reflns_theta_full        25.016
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.669
_diffrn_reflns_point_group_measured_fraction_full 0.669
_reflns_number_total             5834
_reflns_number_gt                4539
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.339
_reflns_Friedel_fraction_max     0.339
_reflns_Friedel_fraction_full    0.339

_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_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33c (release 11-04-2014 CrysAlis171 .NET)
(compiled Apr 11 2014,15:12:41)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33c (release 11-04-2014 CrysAlis171 .NET)
(compiled Apr 11 2014,15:12:41)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33c (release 11-04-2014 CrysAlis171 .NET)
(compiled Apr 11 2014,15:12:41)
;
_computing_molecular_graphics    
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material  
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement  
;
SHELXL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution    
;
SHELXS, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_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)+(0.0413P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Classical Flack method preferred over Parsons because s.u. lower.
;
_refine_ls_abs_structure_Flack   0.01(4)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         5834
_refine_ls_number_parameters     683
_refine_ls_number_restraints     9
_refine_ls_R_factor_all          0.0856
_refine_ls_R_factor_gt           0.0621
_refine_ls_wR_factor_ref         0.1349
_refine_ls_wR_factor_gt          0.1198
_refine_ls_goodness_of_fit_ref   1.006
_refine_ls_restrained_S_all      1.005
_refine_ls_shift/su_max          0.005
_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 0.32615(14) 0.05815(14) 0.39433(13) 0.0225(4) Uani 1 1 d . . . . .
V2 V -0.19599(14) 0.55536(14) 0.88616(13) 0.0214(4) Uani 1 1 d . . . . .
N1A N 0.4855(8) 0.0469(7) 0.2360(6) 0.0220(18) Uani 1 1 d . . . . .
N2A N 0.4666(7) -0.0383(7) 0.1645(6) 0.0228(17) Uani 1 1 d . . . . .
N3A N 0.5174(8) -0.1762(7) -0.0169(6) 0.0256(18) Uani 1 1 d D . . . .
N4A N 0.4353(7) -0.1348(7) 0.4558(6) 0.0225(17) Uani 1 1 d . . . . .
N5A N 0.1913(7) -0.0085(7) 0.5610(6) 0.0202(17) Uani 1 1 d . . . . .
O1A O 0.4582(6) 0.1225(5) 0.4499(5) 0.0255(15) Uani 1 1 d . . . . .
O2A O 0.2623(6) -0.0632(6) 0.3197(6) 0.0269(16) Uani 1 1 d . . . . .
O3A O 0.2267(6) 0.1857(6) 0.3813(5) 0.0309(17) Uani 1 1 d . . . . .
C1A C 0.6309(9) 0.1886(9) 0.2636(8) 0.020(2) Uani 1 1 d . . . . .
C2A C 0.5592(9) 0.1958(8) 0.3859(8) 0.021(2) Uani 1 1 d . . . . .
C3A C 0.6017(9) 0.2776(8) 0.4451(8) 0.024(2) Uani 1 1 d . . . . .
H3A H 0.555561 0.281695 0.525084 0.029 Uiso 1 1 calc R U . . .
C4A C 0.7087(9) 0.3518(8) 0.3895(8) 0.025(2) Uani 1 1 d . . . . .
H4A H 0.734270 0.404840 0.431788 0.030 Uiso 1 1 calc R U . . .
C5A C 0.7802(9) 0.3479(8) 0.2680(8) 0.022(2) Uani 1 1 d . . . . .
C6A C 0.7372(10) 0.2686(8) 0.2104(8) 0.025(2) Uani 1 1 d . . . . .
H6A H 0.781969 0.267929 0.129789 0.029 Uiso 1 1 calc R U . . .
C7A C 0.5992(9) 0.1007(8) 0.1965(7) 0.023(2) Uani 1 1 d . . . . .
C8A C 0.3464(9) -0.0873(8) 0.2156(8) 0.021(2) Uani 1 1 d . . . . .
C9A C 0.3072(8) -0.1781(8) 0.1512(7) 0.0156(19) Uani 1 1 d . . . . .
C10A C 0.3932(9) -0.2217(8) 0.0453(8) 0.023(2) Uani 1 1 d . . . . .
C11A C 0.3459(10) -0.3114(8) -0.0022(8) 0.029(2) Uani 1 1 d . . . . .
H11A H 0.400789 -0.340348 -0.073786 0.035 Uiso 1 1 calc R U . . .
C12A C 0.2174(10) -0.3579(9) 0.0566(9) 0.032(2) Uani 1 1 d . . . . .
H12A H 0.188615 -0.419628 0.025259 0.038 Uiso 1 1 calc R U . . .
C13A C 0.1343(11) -0.3140(9) 0.1586(8) 0.037(3) Uani 1 1 d . . . . .
H13A H 0.047501 -0.343529 0.196462 0.044 Uiso 1 1 calc R U . . .
C14A C 0.1794(10) -0.2246(9) 0.2065(8) 0.033(2) Uani 1 1 d . . . . .
H14A H 0.122477 -0.195393 0.277403 0.040 Uiso 1 1 calc R U . . .
C15A C 0.7058(10) 0.0705(11) 0.0768(8) 0.043(3) Uani 1 1 d . . . . .
H15A H 0.759917 -0.008701 0.086766 0.064 Uiso 1 1 calc R U . . .
H15B H 0.766128 0.137581 0.046498 0.064 Uiso 1 1 calc R U . . .
H15C H 0.657938 0.063883 0.022579 0.064 Uiso 1 1 calc R U . . .
C16A C 0.8999(10) 0.4304(9) 0.2045(8) 0.034(2) Uani 1 1 d . . . . .
H16A H 0.977186 0.400442 0.231930 0.051 Uiso 1 1 calc R U . . .
H16B H 0.869996 0.517385 0.220506 0.051 Uiso 1 1 calc R U . . .
H16C H 0.927484 0.425209 0.121289 0.051 Uiso 1 1 calc R U . . .
C17A C 0.5598(10) -0.1945(9) 0.4045(9) 0.034(3) Uani 1 1 d . . . . .
H17A H 0.616777 -0.155195 0.334878 0.041 Uiso 1 1 calc R U . . .
C18A C 0.6089(10) -0.3108(9) 0.4485(9) 0.033(2) Uani 1 1 d . . . . .
H18A H 0.696329 -0.348532 0.408473 0.040 Uiso 1 1 calc R U . . .
C19A C 0.5274(11) -0.3709(9) 0.5525(9) 0.036(3) Uani 1 1 d . . . . .
H19A H 0.558504 -0.450013 0.582989 0.044 Uiso 1 1 calc R U . . .
C20A C 0.3958(9) -0.3100(8) 0.6116(8) 0.026(2) Uani 1 1 d . . . . .
C21A C 0.3030(11) -0.3640(9) 0.7200(8) 0.034(2) Uani 1 1 d . . . . .
H21A H 0.329242 -0.443066 0.753934 0.041 Uiso 1 1 calc R U . . .
C22A C 0.1785(10) -0.3025(9) 0.7735(9) 0.031(2) Uani 1 1 d . . . . .
H22A H 0.119827 -0.339611 0.843561 0.037 Uiso 1 1 calc R U . . .
C23A C 0.1355(10) -0.1792(9) 0.7228(8) 0.026(2) Uani 1 1 d . . . . .
C24A C 0.0107(9) -0.1089(9) 0.7772(8) 0.027(2) Uani 1 1 d . . . . .
H24A H -0.049580 -0.140073 0.849096 0.032 Uiso 1 1 calc R U . . .
C25A C -0.0210(10) 0.0067(9) 0.7226(9) 0.031(2) Uani 1 1 d . . . . .
H25A H -0.104143 0.054416 0.757815 0.037 Uiso 1 1 calc R U . . .
C26A C 0.0680(9) 0.0541(9) 0.6162(8) 0.026(2) Uani 1 1 d . . . . .
H26A H 0.041862 0.132465 0.581034 0.031 Uiso 1 1 calc R U . . .
C27A C 0.2251(9) -0.1265(8) 0.6154(8) 0.024(2) Uani 1 1 d . . . . .
C28A C 0.3561(10) -0.1936(9) 0.5586(8) 0.027(2) Uani 1 1 d . . . . .
N1B N -0.0385(7) 0.5403(7) 0.7269(6) 0.0218(18) Uani 1 1 d . . . . .
N2B N 0.0561(7) 0.4313(6) 0.7275(6) 0.0197(17) Uani 1 1 d . . . . .
N3B N 0.2752(8) 0.2642(8) 0.6465(7) 0.031(2) Uani 1 1 d D . . . .
N4B N -0.2935(7) 0.4019(7) 0.8291(6) 0.0255(18) Uani 1 1 d . . . . .
N5B N -0.3732(7) 0.5055(7) 1.0316(6) 0.0212(18) Uani 1 1 d . . . . .
O1B O -0.3011(6) 0.6628(5) 0.7955(5) 0.0239(14) Uani 1 1 d . . . . .
O2B O -0.0818(6) 0.3982(5) 0.9221(5) 0.0236(15) Uani 1 1 d . . . . .
O3B O -0.1534(6) 0.6564(6) 0.9515(5) 0.0250(16) Uani 1 1 d . . . . .
C1B C -0.1130(9) 0.7256(8) 0.6178(8) 0.023(2) Uani 1 1 d . . . . .
C2B C -0.2509(9) 0.7452(8) 0.7003(7) 0.021(2) Uani 1 1 d . . . . .
C3B C -0.3371(9) 0.8489(8) 0.6764(8) 0.024(2) Uani 1 1 d . . . . .
H3B H -0.427828 0.859604 0.727161 0.028 Uiso 1 1 calc R U . . .
C4B C -0.2938(9) 0.9375(9) 0.5797(8) 0.025(2) Uani 1 1 d . . . . .
H4B H -0.355189 1.005373 0.565019 0.030 Uiso 1 1 calc R U . . .
C5B C -0.1545(9) 0.9238(9) 0.5030(8) 0.027(2) Uani 1 1 d . . . . .
C6B C -0.0714(10) 0.8189(9) 0.5237(8) 0.029(2) Uani 1 1 d . . . . .
H6B H 0.018897 0.808807 0.471799 0.034 Uiso 1 1 calc R U . . .
C7B C -0.0192(9) 0.6128(8) 0.6295(8) 0.022(2) Uani 1 1 d . . . . .
C9B C 0.1114(9) 0.2433(8) 0.8453(8) 0.020(2) Uani 1 1 d . . . . .
C8B C 0.0264(9) 0.3650(8) 0.8320(8) 0.023(2) Uani 1 1 d . . . . .
C10B C 0.2237(9) 0.1967(8) 0.7525(8) 0.025(2) Uani 1 1 d . . . . .
C11B C 0.2868(9) 0.0733(8) 0.7727(8) 0.027(2) Uani 1 1 d . . . . .
H12B H 0.360170 0.040104 0.711696 0.033 Uiso 1 1 calc R U . . .
C12B C 0.2445(10) 0.0007(9) 0.8779(9) 0.035(3) Uani 1 1 d . . . . .
H12C H 0.288919 -0.080275 0.888043 0.041 Uiso 1 1 calc R U . . .
C13B C 0.1331(10) 0.0488(8) 0.9713(8) 0.031(2) Uani 1 1 d . . . . .
H13B H 0.103206 0.000187 1.043640 0.037 Uiso 1 1 calc R U . . .
C14B C 0.0694(9) 0.1685(9) 0.9541(8) 0.027(2) Uani 1 1 d . . . . .
H14B H -0.003401 0.200953 1.015970 0.033 Uiso 1 1 calc R U . . .
C15B C 0.1045(9) 0.5745(9) 0.5229(8) 0.032(2) Uani 1 1 d . . . . .
H15D H 0.189403 0.588434 0.534056 0.048 Uiso 1 1 calc R U . . .
H15E H 0.096200 0.625167 0.453081 0.048 Uiso 1 1 calc R U . . .
H15F H 0.105364 0.485997 0.514766 0.048 Uiso 1 1 calc R U . . .
C16B C -0.1048(10) 1.0241(9) 0.4012(9) 0.044(3) Uani 1 1 d . . . . .
H16D H -0.111595 0.997394 0.331187 0.066 Uiso 1 1 calc R U . . .
H16E H -0.009766 1.035642 0.389425 0.066 Uiso 1 1 calc R U . . .
H16F H -0.161294 1.103178 0.418117 0.066 Uiso 1 1 calc R U . . .
C17B C -0.2500(9) 0.3466(9) 0.7315(8) 0.027(2) Uani 1 1 d . . . . .
H17B H -0.170532 0.372567 0.672585 0.033 Uiso 1 1 calc R U . . .
C18B C -0.3162(10) 0.2517(9) 0.7115(9) 0.033(3) Uani 1 1 d . . . . .
H18B H -0.279062 0.214139 0.641428 0.039 Uiso 1 1 calc R U . . .
C19B C -0.4337(10) 0.2132(9) 0.7924(8) 0.034(2) Uani 1 1 d . . . . .
H19B H -0.478963 0.150169 0.778513 0.041 Uiso 1 1 calc R U . . .
C20B C -0.4866(11) 0.2702(9) 0.8984(9) 0.031(2) Uani 1 1 d . . . . .
C21B C -0.6093(10) 0.2364(9) 0.9936(9) 0.035(3) Uani 1 1 d . . . . .
H21B H -0.661852 0.176492 0.984664 0.042 Uiso 1 1 calc R U . . .
C22B C -0.6491(10) 0.2900(9) 1.0955(9) 0.032(2) Uani 1 1 d . . . . .
H22B H -0.729588 0.266451 1.154496 0.038 Uiso 1 1 calc R U . . .
C23B C -0.5725(10) 0.3821(8) 1.1170(8) 0.026(2) Uani 1 1 d . . . . .
C24B C -0.6069(10) 0.4380(8) 1.2198(8) 0.031(2) Uani 1 1 d . . . . .
H24B H -0.684338 0.415711 1.282947 0.037 Uiso 1 1 calc R U . . .
C25B C -0.5289(9) 0.5248(9) 1.2293(9) 0.026(2) Uani 1 1 d . . . . .
H25B H -0.553061 0.562701 1.298796 0.032 Uiso 1 1 calc R U . . .
C26B C -0.4119(9) 0.5584(8) 1.1355(8) 0.027(2) Uani 1 1 d . . . . .
H26B H -0.358916 0.618274 1.143897 0.032 Uiso 1 1 calc R U . . .
C27B C -0.4518(9) 0.4197(9) 1.0211(8) 0.024(2) Uani 1 1 d . . . . .
C28B C -0.4097(10) 0.3627(8) 0.9123(8) 0.024(2) Uani 1 1 d . . . . .
HN3A H 0.536(8) -0.113(6) 0.011(5) 0.029 Uiso 1 1 d D U . . .
HN3B H 0.559(9) -0.165(7) -0.092(2) 0.029 Uiso 1 1 d D U . . .
HN3C H 0.325(7) 0.236(7) 0.581(4) 0.029 Uiso 1 1 d D U . . .
HN3D H 0.224(7) 0.331(5) 0.630(6) 0.029 Uiso 1 1 d D U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
V1 O3A 1.606(6) . ?
V1 O1A 1.942(6) . ?
V1 O2A 1.971(6) . ?
V1 N1A 2.067(8) . ?
V1 N5A 2.118(7) . ?
V1 N4A 2.351(8) . ?
V2 O3B 1.608(6) . ?
V2 O1B 1.946(6) . ?
V2 O2B 1.991(6) . ?
V2 N1B 2.070(7) . ?
V2 N5B 2.130(7) . ?
V2 N4B 2.322(7) . ?
N1A C7A 1.285(11) . ?
N1A N2A 1.415(9) . ?
N2A C8A 1.323(10) . ?
N3A C10A 1.359(11) . ?
N3A HN3A 0.86(2) . ?
N3A HN3B 0.87(2) . ?
N4A C17A 1.333(11) . ?
N4A C28A 1.357(11) . ?
N5A C26A 1.348(10) . ?
N5A C27A 1.390(11) . ?
O1A C2A 1.340(10) . ?
O2A C8A 1.305(10) . ?
C1A C6A 1.400(12) . ?
C1A C2A 1.424(12) . ?
C1A C7A 1.458(11) . ?
C2A C3A 1.400(12) . ?
C3A C4A 1.369(12) . ?
C3A H3A 0.9300 . ?
C4A C5A 1.412(12) . ?
C4A H4A 0.9300 . ?
C5A C6A 1.369(12) . ?
C5A C16A 1.531(12) . ?
C6A H6A 0.9300 . ?
C7A C15A 1.541(12) . ?
C8A C9A 1.497(11) . ?
C9A C14A 1.382(12) . ?
C9A C10A 1.391(11) . ?
C10A C11A 1.398(11) . ?
C11A C12A 1.392(12) . ?
C11A H11A 0.9300 . ?
C12A C13A 1.349(13) . ?
C12A H12A 0.9300 . ?
C13A C14A 1.385(13) . ?
C13A H13A 0.9300 . ?
C14A H14A 0.9300 . ?
C15A H15A 0.9600 . ?
C15A H15B 0.9600 . ?
C15A H15C 0.9600 . ?
C16A H16A 0.9600 . ?
C16A H16B 0.9600 . ?
C16A H16C 0.9600 . ?
C17A C18A 1.376(13) . ?
C17A H17A 0.9300 . ?
C18A C19A 1.381(13) . ?
C18A H18A 0.9300 . ?
C19A C20A 1.414(12) . ?
C19A H19A 0.9300 . ?
C20A C28A 1.388(12) . ?
C20A C21A 1.434(12) . ?
C21A C22A 1.347(13) . ?
C21A H21A 0.9300 . ?
C22A C23A 1.446(12) . ?
C22A H22A 0.9300 . ?
C23A C24A 1.394(12) . ?
C23A C27A 1.409(12) . ?
C24A C25A 1.365(13) . ?
C24A H24A 0.9300 . ?
C25A C26A 1.379(12) . ?
C25A H25A 0.9300 . ?
C26A H26A 0.9300 . ?
C27A C28A 1.429(12) . ?
N1B C7B 1.286(11) . ?
N1B N2B 1.408(9) . ?
N2B C8B 1.320(10) . ?
N3B C10B 1.354(11) . ?
N3B HN3C 0.86(2) . ?
N3B HN3D 0.86(2) . ?
N4B C17B 1.311(10) . ?
N4B C28B 1.350(11) . ?
N5B C27B 1.344(11) . ?
N5B C26B 1.366(10) . ?
O1B C2B 1.343(10) . ?
O2B C8B 1.318(10) . ?
C1B C6B 1.392(12) . ?
C1B C2B 1.440(11) . ?
C1B C7B 1.454(12) . ?
C2B C3B 1.378(12) . ?
C3B C4B 1.383(12) . ?
C3B H3B 0.9300 . ?
C4B C5B 1.419(12) . ?
C4B H4B 0.9300 . ?
C5B C6B 1.356(12) . ?
C5B C16B 1.509(12) . ?
C6B H6B 0.9300 . ?
C7B C15B 1.534(12) . ?
C9B C14B 1.405(12) . ?
C9B C10B 1.403(12) . ?
C9B C8B 1.480(12) . ?
C10B C11B 1.410(11) . ?
C11B C12B 1.361(12) . ?
C11B H12B 0.9300 . ?
C12B C13B 1.409(12) . ?
C12B H12C 0.9300 . ?
C13B C14B 1.372(12) . ?
C13B H13B 0.9300 . ?
C14B H14B 0.9300 . ?
C15B H15D 0.9600 . ?
C15B H15E 0.9600 . ?
C15B H15F 0.9600 . ?
C16B H16D 0.9600 . ?
C16B H16E 0.9600 . ?
C16B H16F 0.9600 . ?
C17B C18B 1.382(12) . ?
C17B H17B 0.9300 . ?
C18B C19B 1.346(13) . ?
C18B H18B 0.9300 . ?
C19B C20B 1.406(13) . ?
C19B H19B 0.9300 . ?
C20B C28B 1.405(12) . ?
C20B C21B 1.441(13) . ?
C21B C22B 1.347(12) . ?
C21B H21B 0.9300 . ?
C22B C23B 1.440(12) . ?
C22B H22B 0.9300 . ?
C23B C24B 1.376(12) . ?
C23B C27B 1.442(12) . ?
C24B C25B 1.343(12) . ?
C24B H24B 0.9300 . ?
C25B C26B 1.395(12) . ?
C25B H25B 0.9300 . ?
C26B H26B 0.9300 . ?
C27B C28B 1.439(12) . ?

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
O3A V1 O1A 101.0(3) . . ?
O3A V1 O2A 102.4(3) . . ?
O1A V1 O2A 154.9(2) . . ?
O3A V1 N1A 107.5(3) . . ?
O1A V1 N1A 86.2(3) . . ?
O2A V1 N1A 78.2(3) . . ?
O3A V1 N5A 94.1(3) . . ?
O1A V1 N5A 97.3(3) . . ?
O2A V1 N5A 90.0(3) . . ?
N1A V1 N5A 157.0(3) . . ?
O3A V1 N4A 167.2(3) . . ?
O1A V1 N4A 79.8(2) . . ?
O2A V1 N4A 79.5(3) . . ?
N1A V1 N4A 85.3(3) . . ?
N5A V1 N4A 73.1(3) . . ?
O3B V2 O1B 102.9(3) . . ?
O3B V2 O2B 101.0(3) . . ?
O1B V2 O2B 154.2(2) . . ?
O3B V2 N1B 106.3(3) . . ?
O1B V2 N1B 85.9(3) . . ?
O2B V2 N1B 78.1(3) . . ?
O3B V2 N5B 94.8(3) . . ?
O1B V2 N5B 95.4(3) . . ?
O2B V2 N5B 92.2(3) . . ?
N1B V2 N5B 158.1(3) . . ?
O3B V2 N4B 168.1(3) . . ?
O1B V2 N4B 79.5(3) . . ?
O2B V2 N4B 79.2(3) . . ?
N1B V2 N4B 85.5(3) . . ?
N5B V2 N4B 73.3(3) . . ?
C7A N1A N2A 116.5(7) . . ?
C7A N1A V1 129.9(6) . . ?
N2A N1A V1 113.5(5) . . ?
C8A N2A N1A 110.3(7) . . ?
C10A N3A HN3A 115(5) . . ?
C10A N3A HN3B 130(5) . . ?
HN3A N3A HN3B 105(4) . . ?
C17A N4A C28A 116.4(8) . . ?
C17A N4A V1 130.0(7) . . ?
C28A N4A V1 113.6(6) . . ?
C26A N5A C27A 116.8(8) . . ?
C26A N5A V1 123.6(6) . . ?
C27A N5A V1 119.5(6) . . ?
C2A O1A V1 126.3(5) . . ?
C8A O2A V1 114.3(5) . . ?
C6A C1A C2A 116.6(8) . . ?
C6A C1A C7A 120.9(8) . . ?
C2A C1A C7A 122.5(8) . . ?
O1A C2A C3A 117.5(8) . . ?
O1A C2A C1A 123.6(8) . . ?
C3A C2A C1A 118.7(8) . . ?
C4A C3A C2A 122.4(8) . . ?
C4A C3A H3A 118.8 . . ?
C2A C3A H3A 118.8 . . ?
C3A C4A C5A 120.0(8) . . ?
C3A C4A H4A 120.0 . . ?
C5A C4A H4A 120.0 . . ?
C6A C5A C4A 117.3(8) . . ?
C6A C5A C16A 122.0(8) . . ?
C4A C5A C16A 120.6(8) . . ?
C5A C6A C1A 124.9(8) . . ?
C5A C6A H6A 117.6 . . ?
C1A C6A H6A 117.6 . . ?
N1A C7A C1A 121.3(8) . . ?
N1A C7A C15A 119.7(8) . . ?
C1A C7A C15A 119.0(8) . . ?
O2A C8A N2A 123.6(8) . . ?
O2A C8A C9A 118.5(7) . . ?
N2A C8A C9A 117.8(7) . . ?
C14A C9A C10A 119.7(8) . . ?
C14A C9A C8A 115.9(8) . . ?
C10A C9A C8A 124.3(7) . . ?
N3A C10A C9A 123.1(7) . . ?
N3A C10A C11A 118.6(8) . . ?
C9A C10A C11A 118.3(8) . . ?
C12A C11A C10A 120.6(9) . . ?
C12A C11A H11A 119.7 . . ?
C10A C11A H11A 119.7 . . ?
C13A C12A C11A 120.5(9) . . ?
C13A C12A H12A 119.7 . . ?
C11A C12A H12A 119.7 . . ?
C12A C13A C14A 119.5(9) . . ?
C12A C13A H13A 120.3 . . ?
C14A C13A H13A 120.3 . . ?
C13A C14A C9A 121.3(9) . . ?
C13A C14A H14A 119.3 . . ?
C9A C14A H14A 119.3 . . ?
C7A C15A H15A 109.5 . . ?
C7A C15A H15B 109.5 . . ?
H15A C15A H15B 109.5 . . ?
C7A C15A H15C 109.5 . . ?
H15A C15A H15C 109.5 . . ?
H15B C15A H15C 109.5 . . ?
C5A C16A H16A 109.5 . . ?
C5A C16A H16B 109.5 . . ?
H16A C16A H16B 109.5 . . ?
C5A C16A H16C 109.5 . . ?
H16A C16A H16C 109.5 . . ?
H16B C16A H16C 109.5 . . ?
N4A C17A C18A 123.9(10) . . ?
N4A C17A H17A 118.0 . . ?
C18A C17A H17A 118.0 . . ?
C19A C18A C17A 119.5(9) . . ?
C19A C18A H18A 120.3 . . ?
C17A C18A H18A 120.3 . . ?
C18A C19A C20A 118.7(9) . . ?
C18A C19A H19A 120.6 . . ?
C20A C19A H19A 120.6 . . ?
C28A C20A C19A 116.9(9) . . ?
C28A C20A C21A 119.8(8) . . ?
C19A C20A C21A 123.3(9) . . ?
C22A C21A C20A 121.3(9) . . ?
C22A C21A H21A 119.3 . . ?
C20A C21A H21A 119.3 . . ?
C21A C22A C23A 120.4(9) . . ?
C21A C22A H22A 119.8 . . ?
C23A C22A H22A 119.8 . . ?
C24A C23A C27A 118.6(8) . . ?
C24A C23A C22A 122.8(8) . . ?
C27A C23A C22A 118.6(8) . . ?
C25A C24A C23A 118.6(9) . . ?
C25A C24A H24A 120.7 . . ?
C23A C24A H24A 120.7 . . ?
C24A C25A C26A 121.1(9) . . ?
C24A C25A H25A 119.4 . . ?
C26A C25A H25A 119.4 . . ?
N5A C26A C25A 122.8(9) . . ?
N5A C26A H26A 118.6 . . ?
C25A C26A H26A 118.6 . . ?
N5A C27A C23A 122.0(8) . . ?
N5A C27A C28A 117.5(8) . . ?
C23A C27A C28A 120.5(8) . . ?
N4A C28A C20A 124.5(9) . . ?
N4A C28A C27A 116.0(8) . . ?
C20A C28A C27A 119.4(9) . . ?
C7B N1B N2B 117.3(7) . . ?
C7B N1B V2 129.3(6) . . ?
N2B N1B V2 113.3(5) . . ?
C8B N2B N1B 111.8(7) . . ?
C10B N3B HN3C 128(5) . . ?
C10B N3B HN3D 117(5) . . ?
HN3C N3B HN3D 106(4) . . ?
C17B N4B C28B 116.8(8) . . ?
C17B N4B V2 129.7(6) . . ?
C28B N4B V2 113.5(6) . . ?
C27B N5B C26B 118.1(8) . . ?
C27B N5B V2 119.2(6) . . ?
C26B N5B V2 122.7(6) . . ?
C2B O1B V2 127.0(5) . . ?
C8B O2B V2 114.1(6) . . ?
C6B C1B C2B 117.5(8) . . ?
C6B C1B C7B 120.2(8) . . ?
C2B C1B C7B 122.3(8) . . ?
O1B C2B C3B 118.9(8) . . ?
O1B C2B C1B 122.6(8) . . ?
C3B C2B C1B 118.3(8) . . ?
C2B C3B C4B 122.5(8) . . ?
C2B C3B H3B 118.7 . . ?
C4B C3B H3B 118.7 . . ?
C3B C4B C5B 119.2(9) . . ?
C3B C4B H4B 120.4 . . ?
C5B C4B H4B 120.4 . . ?
C6B C5B C4B 118.2(9) . . ?
C6B C5B C16B 122.4(9) . . ?
C4B C5B C16B 119.4(8) . . ?
C5B C6B C1B 124.0(9) . . ?
C5B C6B H6B 118.0 . . ?
C1B C6B H6B 118.0 . . ?
N1B C7B C1B 122.0(8) . . ?
N1B C7B C15B 117.9(8) . . ?
C1B C7B C15B 120.1(8) . . ?
C14B C9B C10B 119.6(8) . . ?
C14B C9B C8B 117.3(8) . . ?
C10B C9B C8B 122.9(8) . . ?
O2B C8B N2B 122.5(8) . . ?
O2B C8B C9B 118.9(8) . . ?
N2B C8B C9B 118.4(8) . . ?
N3B C10B C9B 123.7(8) . . ?
N3B C10B C11B 118.8(8) . . ?
C9B C10B C11B 117.5(9) . . ?
C12B C11B C10B 122.6(9) . . ?
C12B C11B H12B 118.7 . . ?
C10B C11B H12B 118.7 . . ?
C11B C12B C13B 119.6(9) . . ?
C11B C12B H12C 120.2 . . ?
C13B C12B H12C 120.2 . . ?
C14B C13B C12B 119.1(9) . . ?
C14B C13B H13B 120.5 . . ?
C12B C13B H13B 120.5 . . ?
C13B C14B C9B 121.6(9) . . ?
C13B C14B H14B 119.2 . . ?
C9B C14B H14B 119.2 . . ?
C7B C15B H15D 109.5 . . ?
C7B C15B H15E 109.5 . . ?
H15D C15B H15E 109.5 . . ?
C7B C15B H15F 109.5 . . ?
H15D C15B H15F 109.5 . . ?
H15E C15B H15F 109.5 . . ?
C5B C16B H16D 109.5 . . ?
C5B C16B H16E 109.5 . . ?
H16D C16B H16E 109.5 . . ?
C5B C16B H16F 109.5 . . ?
H16D C16B H16F 109.5 . . ?
H16E C16B H16F 109.5 . . ?
N4B C17B C18B 123.3(9) . . ?
N4B C17B H17B 118.3 . . ?
C18B C17B H17B 118.3 . . ?
C19B C18B C17B 120.7(9) . . ?
C19B C18B H18B 119.6 . . ?
C17B C18B H18B 119.6 . . ?
C18B C19B C20B 118.5(9) . . ?
C18B C19B H19B 120.7 . . ?
C20B C19B H19B 120.7 . . ?
C28B C20B C19B 116.6(9) . . ?
C28B C20B C21B 118.8(9) . . ?
C19B C20B C21B 124.5(9) . . ?
C22B C21B C20B 121.2(10) . . ?
C22B C21B H21B 119.4 . . ?
C20B C21B H21B 119.4 . . ?
C21B C22B C23B 122.8(10) . . ?
C21B C22B H22B 118.6 . . ?
C23B C22B H22B 118.6 . . ?
C24B C23B C22B 125.3(9) . . ?
C24B C23B C27B 118.1(9) . . ?
C22B C23B C27B 116.6(8) . . ?
C25B C24B C23B 120.2(9) . . ?
C25B C24B H24B 119.9 . . ?
C23B C24B H24B 119.9 . . ?
C24B C25B C26B 120.5(9) . . ?
C24B C25B H25B 119.8 . . ?
C26B C25B H25B 119.8 . . ?
N5B C26B C25B 121.7(9) . . ?
N5B C26B H26B 119.2 . . ?
C25B C26B H26B 119.2 . . ?
N5B C27B C28B 118.0(8) . . ?
N5B C27B C23B 121.5(8) . . ?
C28B C27B C23B 120.4(8) . . ?
N4B C28B C20B 124.0(9) . . ?
N4B C28B C27B 115.9(8) . . ?
C20B C28B C27B 120.1(9) . . ?

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
C26A H26A O3A 0.93 2.57 3.017(11) 110.1 .
C17B H17B N1B 0.93 2.66 3.177(12) 115.9 .
C26B H26B O3B 0.93 2.59 3.036(11) 110.0 .
N3A HN3A N2A 0.86(2) 1.99(5) 2.684(10) 136(6) .
N3A HN3B O1B 0.87(2) 2.44(7) 2.994(9) 122(7) 1_644
N3B HN3C O1A 0.86(2) 2.12(3) 2.952(10) 164(7) .
N3B HN3D N2B 0.86(2) 2.00(5) 2.664(10) 133(6) .

_refine_diff_density_max         0.393
_refine_diff_density_min         -0.367
_refine_diff_density_rms         0.070

####################################################################### 
# 
# 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 1887601'
_audit_update_record             
;
2018-12-27 deposited with the CCDC.	2019-10-01 downloaded from the CCDC.
;




_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C24 H19 N4 O4 V'
_chemical_formula_weight         478.37

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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

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

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.8475(5)
_cell_length_b                   10.8678(9)
_cell_length_c                   14.0113(12)
_cell_angle_alpha                68.768(8)
_cell_angle_beta                 77.151(7)
_cell_angle_gamma                72.756(7)
_cell_volume                     1054.86(16)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    6315
_cell_measurement_theta_min      3.33
_cell_measurement_theta_max      27.50

_exptl_crystal_description       needle
_exptl_crystal_colour            black
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.506
_exptl_crystal_F_000             492
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.03
_exptl_absorpt_coefficient_mu    0.511
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   'ABSPACK, Oxford Diffraction Ltd'
_exptl_absorpt_correction_T_min  0.933
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Oxford Diffaction X-Calibor System'
_diffrn_measurement_method       '321 frames, counting time 10 s.'
_diffrn_standards_interval_count n/a
_diffrn_standards_interval_time  n/a
_diffrn_standards_decay_%        n/a
_diffrn_reflns_number            6315
_diffrn_reflns_av_unetI/netI     0.0526
_diffrn_reflns_av_R_equivalents  0.0199
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         3.332
_diffrn_reflns_theta_max         27.497
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.972
_diffrn_measured_fraction_theta_full 0.982
_diffrn_reflns_Laue_measured_fraction_max 0.972
_diffrn_reflns_Laue_measured_fraction_full 0.982
_diffrn_reflns_point_group_measured_fraction_max 0.972
_diffrn_reflns_point_group_measured_fraction_full 0.982
_reflns_number_total             4712
_reflns_number_gt                3958
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Crysalis, Oxford Diffraction'
_computing_cell_refinement       'Crysalis, Oxford Diffraction'
_computing_data_reduction        'Crysalis, Oxford Diffraction'
_computing_structure_solution    'SHELXS (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL (Sheldrick, 2008)'
_computing_molecular_graphics    PLATON(Spek,2004)
_computing_publication_material  'SHELXL, PLATON, WINGX (Ferrugia, 2012)'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0430P)²+0.3954P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4712
_refine_ls_number_parameters     305
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0559
_refine_ls_R_factor_gt           0.0441
_refine_ls_wR_factor_ref         0.1041
_refine_ls_wR_factor_gt          0.0984
_refine_ls_goodness_of_fit_ref   1.012
_refine_ls_restrained_S_all      1.012
_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
V V 0.27127(5) 0.30915(4) 0.30641(3) 0.01871(11) Uani 1 1 d . . . . .
N1 N 0.1751(2) 0.45603(17) 0.17109(13) 0.0192(4) Uani 1 1 d . . . . .
N2 N 0.2648(2) 0.43009(18) 0.07965(13) 0.0212(4) Uani 1 1 d . . . . .
N3 N 0.3900(3) 0.4661(2) -0.12213(14) 0.0274(4) Uani 1 1 d D . . . .
HN3A H 0.423(3) 0.516(2) -0.1811(13) 0.033 Uiso 1 1 d D U . . .
HN3B H 0.336(3) 0.510(2) -0.0794(15) 0.033 Uiso 1 1 d D U . . .
N4 N 0.0703(2) 0.19898(18) 0.29199(13) 0.0206(4) Uani 1 1 d . . . . .
O1 O 0.0740(2) 0.40020(15) 0.37119(11) 0.0304(4) Uani 1 1 d . . . . .
O2 O 0.40634(19) 0.23821(14) 0.19667(10) 0.0209(3) Uani 1 1 d . . . . .
O3 O 0.4221(2) 0.37200(16) 0.31939(11) 0.0296(4) Uani 1 1 d . . . . .
O4 O 0.32789(19) 0.13881(14) 0.40318(10) 0.0195(3) Uani 1 1 d . . . . .
C1 C -0.0714(3) 0.6008(2) 0.24660(16) 0.0200(4) Uani 1 1 d . . . . .
C2 C -0.0561(3) 0.5143(2) 0.34913(16) 0.0209(4) Uani 1 1 d . . . . .
C3 C -0.1778(3) 0.5453(2) 0.43114(17) 0.0252(5) Uani 1 1 d . . . . .
H3 H -0.165261 0.487914 0.498352 0.030 Uiso 1 1 calc R U . . .
C4 C -0.3153(3) 0.6592(2) 0.41329(18) 0.0288(5) Uani 1 1 d . . . . .
H4 H -0.395904 0.679004 0.468416 0.035 Uiso 1 1 calc R U . . .
C5 C -0.3356(3) 0.7458(2) 0.31334(19) 0.0328(6) Uani 1 1 d . . . . .
H5 H -0.430185 0.822845 0.301481 0.039 Uiso 1 1 calc R U . . .
C6 C -0.2155(3) 0.7172(2) 0.23194(18) 0.0270(5) Uani 1 1 d . . . . .
H6 H -0.229682 0.776310 0.165360 0.032 Uiso 1 1 calc R U . . .
C7 C 0.0474(3) 0.5683(2) 0.15841(16) 0.0209(4) Uani 1 1 d . . . . .
C8 C 0.3826(3) 0.3128(2) 0.10117(15) 0.0181(4) Uani 1 1 d . . . . .
C9 C 0.4932(3) 0.2602(2) 0.01859(16) 0.0207(4) Uani 1 1 d . . . . .
C10 C 0.4997(3) 0.3389(2) -0.08770(16) 0.0226(5) Uani 1 1 d . . . . .
C11 C 0.6180(3) 0.2809(3) -0.15894(18) 0.0306(5) Uani 1 1 d . . . . .
H11 H 0.625251 0.331775 -0.228620 0.037 Uiso 1 1 calc R U . . .
C12 C 0.7238(4) 0.1516(3) -0.1294(2) 0.0403(6) Uani 1 1 d . . . . .
H12 H 0.801179 0.116134 -0.178833 0.048 Uiso 1 1 calc R U . . .
C13 C 0.7157(4) 0.0730(3) -0.0255(2) 0.0401(6) Uani 1 1 d . . . . .
H13 H 0.786554 -0.015196 -0.005182 0.048 Uiso 1 1 calc R U . . .
C14 C 0.6017(3) 0.1277(2) 0.04642(17) 0.0278(5) Uani 1 1 d . . . . .
H14 H 0.596280 0.075136 0.115718 0.033 Uiso 1 1 calc R U . . .
C15 C 0.0189(3) 0.6625(2) 0.05074(17) 0.0312(5) Uani 1 1 d . . . . .
H15A H 0.133142 0.673926 0.011104 0.047 Uiso 1 1 calc R U . . .
H15B H -0.055179 0.749144 0.053972 0.047 Uiso 1 1 calc R U . . .
H15C H -0.039231 0.624466 0.018521 0.047 Uiso 1 1 calc R U . . .
C16 C -0.0675(3) 0.2353(2) 0.23999(17) 0.0278(5) Uani 1 1 d . . . . .
H16 H -0.100174 0.325197 0.198516 0.033 Uiso 1 1 calc R U . . .
C17 C -0.1661(3) 0.1456(3) 0.24418(19) 0.0343(6) Uani 1 1 d . . . . .
H17 H -0.263297 0.176074 0.206971 0.041 Uiso 1 1 calc R U . . .
C18 C -0.1193(3) 0.0125(3) 0.30330(18) 0.0313(5) Uani 1 1 d . . . . .
H18 H -0.183275 -0.048426 0.305717 0.038 Uiso 1 1 calc R U . . .
C19 C 0.0277(3) -0.0325(2) 0.36111(16) 0.0235(5) Uani 1 1 d . . . . .
C20 C 0.0869(3) -0.1657(2) 0.42788(18) 0.0277(5) Uani 1 1 d . . . . .
H20 H 0.031834 -0.233686 0.434313 0.033 Uiso 1 1 calc R U . . .
C21 C 0.2250(3) -0.1943(2) 0.48286(17) 0.0261(5) Uani 1 1 d . . . . .
H21 H 0.262909 -0.282495 0.526118 0.031 Uiso 1 1 calc R U . . .
C22 C 0.3124(3) -0.0944(2) 0.47625(16) 0.0222(5) Uani 1 1 d . . . . .
H22 H 0.405420 -0.116393 0.515051 0.027 Uiso 1 1 calc R U . . .
C23 C 0.2576(3) 0.0360(2) 0.41150(15) 0.0179(4) Uani 1 1 d . . . . .
C24 C 0.1160(3) 0.0674(2) 0.35261(15) 0.0193(4) 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 O3 1.6015(16) . ?
V O1 1.8212(16) . ?
V O4 1.8508(14) . ?
V O2 1.9316(15) . ?
V N1 2.1077(17) . ?
V N4 2.3235(18) . ?
N1 C7 1.312(3) . ?
N1 N2 1.400(2) . ?
N2 C8 1.310(3) . ?
N3 C10 1.372(3) . ?
N3 HN3A 0.841(15) . ?
N3 HN3B 0.859(15) . ?
N4 C16 1.321(3) . ?
N4 C24 1.359(3) . ?
O1 C2 1.337(3) . ?
O2 C8 1.311(2) . ?
O4 C23 1.345(2) . ?
C1 C6 1.410(3) . ?
C1 C2 1.412(3) . ?
C1 C7 1.459(3) . ?
C2 C3 1.396(3) . ?
C3 C4 1.365(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.388(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.375(3) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C7 C15 1.507(3) . ?
C8 C9 1.469(3) . ?
C9 C14 1.402(3) . ?
C9 C10 1.422(3) . ?
C10 C11 1.397(3) . ?
C11 C12 1.369(4) . ?
C11 H11 0.9300 . ?
C12 C13 1.394(4) . ?
C12 H12 0.9300 . ?
C13 C14 1.374(3) . ?
C13 H13 0.9300 . ?
C14 H14 0.9300 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C16 C17 1.393(3) . ?
C16 H16 0.9300 . ?
C17 C18 1.366(3) . ?
C17 H17 0.9300 . ?
C18 C19 1.421(3) . ?
C18 H18 0.9300 . ?
C19 C24 1.410(3) . ?
C19 C20 1.414(3) . ?
C20 C21 1.365(3) . ?
C20 H20 0.9300 . ?
C21 C22 1.413(3) . ?
C21 H21 0.9300 . ?
C22 C23 1.377(3) . ?
C22 H22 0.9300 . ?
C23 C24 1.419(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O3 V O1 99.69(8) . . ?
O3 V O4 98.99(7) . . ?
O1 V O4 103.88(7) . . ?
O3 V O2 97.44(7) . . ?
O1 V O2 155.29(7) . . ?
O4 V O2 90.80(6) . . ?
O3 V N1 100.83(7) . . ?
O1 V N1 83.74(7) . . ?
O4 V N1 157.23(7) . . ?
O2 V N1 75.63(6) . . ?
O3 V N4 174.86(8) . . ?
O1 V N4 83.96(7) . . ?
O4 V N4 76.53(6) . . ?
O2 V N4 80.24(6) . . ?
N1 V N4 83.11(6) . . ?
C7 N1 N2 114.91(17) . . ?
C7 N1 V 130.76(14) . . ?
N2 N1 V 114.32(13) . . ?
C8 N2 N1 109.92(17) . . ?
C10 N3 HN3A 116.6(17) . . ?
C10 N3 HN3B 119.9(17) . . ?
HN3A N3 HN3B 114(2) . . ?
C16 N4 C24 117.68(19) . . ?
C16 N4 V 135.01(15) . . ?
C24 N4 V 107.31(13) . . ?
C2 O1 V 139.63(14) . . ?
C8 O2 V 118.37(13) . . ?
C23 O4 V 122.99(12) . . ?
C6 C1 C2 116.8(2) . . ?
C6 C1 C7 120.7(2) . . ?
C2 C1 C7 122.32(19) . . ?
O1 C2 C3 117.70(19) . . ?
O1 C2 C1 121.56(19) . . ?
C3 C2 C1 120.7(2) . . ?
C4 C3 C2 120.4(2) . . ?
C4 C3 H3 119.8 . . ?
C2 C3 H3 119.8 . . ?
C3 C4 C5 120.4(2) . . ?
C3 C4 H4 119.8 . . ?
C5 C4 H4 119.8 . . ?
C6 C5 C4 119.8(2) . . ?
C6 C5 H5 120.1 . . ?
C4 C5 H5 120.1 . . ?
C5 C6 C1 121.8(2) . . ?
C5 C6 H6 119.1 . . ?
C1 C6 H6 119.1 . . ?
N1 C7 C1 121.08(19) . . ?
N1 C7 C15 119.34(19) . . ?
C1 C7 C15 119.54(19) . . ?
N2 C8 O2 121.51(19) . . ?
N2 C8 C9 120.94(18) . . ?
O2 C8 C9 117.55(18) . . ?
C14 C9 C10 118.6(2) . . ?
C14 C9 C8 118.27(19) . . ?
C10 C9 C8 123.1(2) . . ?
N3 C10 C11 119.6(2) . . ?
N3 C10 C9 122.4(2) . . ?
C11 C10 C9 118.0(2) . . ?
C12 C11 C10 122.1(2) . . ?
C12 C11 H11 119.0 . . ?
C10 C11 H11 119.0 . . ?
C11 C12 C13 120.2(2) . . ?
C11 C12 H12 119.9 . . ?
C13 C12 H12 119.9 . . ?
C14 C13 C12 119.0(2) . . ?
C14 C13 H13 120.5 . . ?
C12 C13 H13 120.5 . . ?
C13 C14 C9 122.0(2) . . ?
C13 C14 H14 119.0 . . ?
C9 C14 H14 119.0 . . ?
C7 C15 H15A 109.5 . . ?
C7 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C7 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
N4 C16 C17 123.3(2) . . ?
N4 C16 H16 118.4 . . ?
C17 C16 H16 118.4 . . ?
C18 C17 C16 119.6(2) . . ?
C18 C17 H17 120.2 . . ?
C16 C17 H17 120.2 . . ?
C17 C18 C19 119.7(2) . . ?
C17 C18 H18 120.1 . . ?
C19 C18 H18 120.1 . . ?
C24 C19 C20 118.3(2) . . ?
C24 C19 C18 115.9(2) . . ?
C20 C19 C18 125.7(2) . . ?
C21 C20 C19 119.9(2) . . ?
C21 C20 H20 120.0 . . ?
C19 C20 H20 120.0 . . ?
C20 C21 C22 122.2(2) . . ?
C20 C21 H21 118.9 . . ?
C22 C21 H21 118.9 . . ?
C23 C22 C21 119.0(2) . . ?
C23 C22 H22 120.5 . . ?
C21 C22 H22 120.5 . . ?
O4 C23 C22 123.21(19) . . ?
O4 C23 C24 117.09(18) . . ?
C22 C23 C24 119.66(19) . . ?
N4 C24 C19 123.83(19) . . ?
N4 C24 C23 115.27(19) . . ?
C19 C24 C23 120.86(19) . . ?

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
C17 H17 O2 0.93 2.50 3.349(3) 151.7 1_455
C22 H22 O4 0.93 2.51 3.432(3) 169.9 2_656
N3 HN3A O3 0.841(15) 2.200(16) 3.019(2) 165(2) 2_665
N3 HN3B N2 0.859(15) 2.089(19) 2.702(3) 128(2) .

_refine_diff_density_max         0.333
_refine_diff_density_min         -0.365
_refine_diff_density_rms         0.059

####################################################################### 
# 
# 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 1887602'
_audit_update_record             
;
2019-09-10 deposited with the CCDC.	2019-10-01 downloaded from the CCDC.
;



_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C24 H18 Cl N4 O4 V'
_chemical_formula_weight         512.81

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'
Cl Cl 0.1484 0.1585 '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                   12.6574(4)
_cell_length_b                   7.6841(2)
_cell_length_c                   22.0915(7)
_cell_angle_alpha                90
_cell_angle_beta                 91.060(3)
_cell_angle_gamma                90
_cell_volume                     2148.27(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    7242
_cell_measurement_theta_min      1.840
_cell_measurement_theta_max      25.027

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.586
_exptl_crystal_F_000             1048
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_absorpt_coefficient_mu    0.628
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            7242
_diffrn_reflns_av_unetI/netI     0.0362
_diffrn_reflns_av_R_equivalents  0.0243
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -3
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         1.840
_diffrn_reflns_theta_max         25.027
_diffrn_reflns_theta_full        25.027
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             3795
_reflns_number_gt                3344
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0473P)²+1.2584P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3795
_refine_ls_number_parameters     319
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0411
_refine_ls_R_factor_gt           0.0354
_refine_ls_wR_factor_ref         0.0967
_refine_ls_wR_factor_gt          0.0920
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_restrained_S_all      1.051
_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 0.97576(3) 0.19516(5) 0.13502(2) 0.01571(13) Uani 1 1 d . . . . .
N1 N 1.01890(14) -0.0438(2) 0.09657(8) 0.0153(4) Uani 1 1 d . . . . .
N2 N 1.11216(14) -0.0392(2) 0.06394(8) 0.0169(4) Uani 1 1 d . . . . .
N3 N 1.27912(17) -0.1364(3) -0.00445(9) 0.0225(5) Uani 1 1 d D . . . .
N4 N 1.08768(14) 0.1384(2) 0.22067(8) 0.0171(4) Uani 1 1 d . . . . .
O1 O 0.88706(13) 0.0588(2) 0.17899(7) 0.0215(4) Uani 1 1 d . . . . .
O2 O 1.11028(12) 0.24165(19) 0.09821(7) 0.0178(3) Uani 1 1 d . . . . .
O3 O 0.90027(13) 0.2538(2) 0.08045(7) 0.0220(4) Uani 1 1 d . . . . .
O4 O 0.97540(12) 0.40103(19) 0.17875(7) 0.0172(3) Uani 1 1 d . . . . .
Cl1 Cl 0.64749(5) -0.58446(8) 0.14459(3) 0.02718(17) Uani 1 1 d . . . . .
C1 C 0.86719(18) -0.2112(3) 0.12608(10) 0.0153(5) Uani 1 1 d . . . . .
C2 C 0.83151(18) -0.0855(3) 0.16732(10) 0.0163(5) Uani 1 1 d . . . . .
C3 C 0.73914(19) -0.1132(3) 0.19956(10) 0.0203(5) Uani 1 1 d . . . . .
H3 H 0.715529 -0.028553 0.226171 0.024 Uiso 1 1 calc R U . . .
C4 C 0.68273(19) -0.2657(3) 0.19213(10) 0.0206(5) Uani 1 1 d . . . . .
H4 H 0.621389 -0.284424 0.213722 0.025 Uiso 1 1 calc R U . . .
C5 C 0.71835(18) -0.3901(3) 0.15228(10) 0.0195(5) Uani 1 1 d . . . . .
C6 C 0.80742(17) -0.3651(3) 0.11937(10) 0.0157(5) Uani 1 1 d . . . . .
H6 H 0.828813 -0.450279 0.092325 0.019 Uiso 1 1 calc R U . . .
C7 C 0.96567(18) -0.1899(3) 0.09359(9) 0.0152(5) Uani 1 1 d . . . . .
C8 C 1.15284(18) 0.1181(3) 0.06630(10) 0.0161(5) Uani 1 1 d . . . . .
C9 C 1.24822(17) 0.1605(3) 0.03207(10) 0.0165(5) Uani 1 1 d . . . . .
C10 C 1.30420(18) 0.0378(3) -0.00307(10) 0.0181(5) Uani 1 1 d . . . . .
C11 C 1.39165(19) 0.0963(3) -0.03523(11) 0.0228(5) Uani 1 1 d . . . . .
H11 H 1.428378 0.017932 -0.059074 0.027 Uiso 1 1 calc R U . . .
C12 C 1.4245(2) 0.2666(3) -0.03240(11) 0.0270(6) Uani 1 1 d . . . . .
H12 H 1.483041 0.301766 -0.054141 0.032 Uiso 1 1 calc R U . . .
C13 C 1.3713(2) 0.3863(3) 0.00255(11) 0.0260(6) Uani 1 1 d . . . . .
H13 H 1.393984 0.501269 0.004714 0.031 Uiso 1 1 calc R U . . .
C14 C 1.28452(19) 0.3331(3) 0.03395(10) 0.0204(5) Uani 1 1 d . . . . .
H14 H 1.248627 0.413926 0.057210 0.024 Uiso 1 1 calc R U . . .
C15 C 1.00634(19) -0.3365(3) 0.05597(11) 0.0214(5) Uani 1 1 d . . . . .
H15A H 0.958965 -0.433720 0.058388 0.015(12) Uiso 0.5 1 calc R . P . .
H15B H 1.011042 -0.299474 0.014608 0.029(15) Uiso 0.5 1 calc R . P . .
H15C H 1.075085 -0.370355 0.070801 0.047(18) Uiso 0.5 1 calc R . P . .
H15D H 1.071096 -0.301979 0.037477 0.035(16) Uiso 0.5 1 calc R . P . .
H15E H 1.019019 -0.436226 0.081257 0.036(16) Uiso 0.5 1 calc R . P . .
H15F H 0.954976 -0.365344 0.025063 0.025(14) Uiso 0.5 1 calc R . P . .
C16 C 1.14075(19) 0.0025(3) 0.24169(11) 0.0224(5) Uani 1 1 d . . . . .
H16 H 1.143085 -0.097648 0.218122 0.027 Uiso 1 1 calc R U . . .
C17 C 1.19425(19) 0.0028(3) 0.29859(11) 0.0257(6) Uani 1 1 d . . . . .
H17 H 1.231500 -0.094990 0.311618 0.031 Uiso 1 1 calc R U . . .
C18 C 1.19062(19) 0.1474(4) 0.33396(11) 0.0269(6) Uani 1 1 d . . . . .
H18 H 1.225477 0.148926 0.371391 0.032 Uiso 1 1 calc R U . . .
C19 C 1.13385(19) 0.2953(3) 0.31380(10) 0.0207(5) Uani 1 1 d . . . . .
C20 C 1.1227(2) 0.4515(3) 0.34694(11) 0.0265(6) Uani 1 1 d . . . . .
H20 H 1.154116 0.461947 0.385151 0.032 Uiso 1 1 calc R U . . .
C21 C 1.0660(2) 0.5868(3) 0.32307(11) 0.0244(6) Uani 1 1 d . . . . .
H21 H 1.059752 0.688873 0.345337 0.029 Uiso 1 1 calc R U . . .
C22 C 1.01657(19) 0.5757(3) 0.26525(10) 0.0199(5) Uani 1 1 d . . . . .
H22 H 0.978439 0.669448 0.249648 0.024 Uiso 1 1 calc R U . . .
C23 C 1.02548(17) 0.4248(3) 0.23240(10) 0.0156(5) Uani 1 1 d . . . . .
C24 C 1.08465(18) 0.2829(3) 0.25614(10) 0.0161(5) Uani 1 1 d . . . . .
HN3A H 1.3025(17) -0.191(3) -0.0338(9) 0.019 Uiso 1 1 d D U . . .
HN3B H 1.2173(14) -0.163(3) 0.0042(10) 0.019 Uiso 1 1 d D U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
V O3 1.5896(16) . ?
V O1 1.8281(17) . ?
V O4 1.8536(15) . ?
V O2 1.9338(16) . ?
V N1 2.0994(18) . ?
V N4 2.3829(19) . ?
N1 C7 1.310(3) . ?
N1 N2 1.395(3) . ?
N2 C8 1.314(3) . ?
N3 C10 1.376(3) . ?
N3 HN3A 0.831(15) . ?
N3 HN3B 0.833(15) . ?
N4 C16 1.322(3) . ?
N4 C24 1.359(3) . ?
O1 C2 1.336(3) . ?
O2 C8 1.305(3) . ?
O4 C23 1.346(3) . ?
Cl1 C5 1.749(2) . ?
C1 C2 1.408(3) . ?
C1 C6 1.410(3) . ?
C1 C7 1.459(3) . ?
C2 C3 1.396(3) . ?
C3 C4 1.380(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.381(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.366(3) . ?
C6 H6 0.9300 . ?
C7 C15 1.497(3) . ?
C8 C9 1.473(3) . ?
C9 C14 1.404(3) . ?
C9 C10 1.419(3) . ?
C10 C11 1.400(3) . ?
C11 C12 1.375(4) . ?
C11 H11 0.9300 . ?
C12 C13 1.384(4) . ?
C12 H12 0.9300 . ?
C13 C14 1.372(3) . ?
C13 H13 0.9300 . ?
C14 H14 0.9300 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C15 H15D 0.9600 . ?
C15 H15E 0.9600 . ?
C15 H15F 0.9600 . ?
C16 C17 1.417(3) . ?
C16 H16 0.9300 . ?
C17 C18 1.360(4) . ?
C17 H17 0.9300 . ?
C18 C19 1.412(3) . ?
C18 H18 0.9300 . ?
C19 C24 1.411(3) . ?
C19 C20 1.414(3) . ?
C20 C21 1.364(4) . ?
C20 H20 0.9300 . ?
C21 C22 1.415(3) . ?
C21 H21 0.9300 . ?
C22 C23 1.373(3) . ?
C22 H22 0.9300 . ?
C23 C24 1.418(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O3 V O1 101.48(8) . . ?
O3 V O4 98.40(7) . . ?
O1 V O4 101.81(7) . . ?
O3 V O2 98.64(8) . . ?
O1 V O2 152.07(7) . . ?
O4 V O2 94.14(7) . . ?
O3 V N1 95.64(8) . . ?
O1 V N1 83.15(7) . . ?
O4 V N1 163.81(7) . . ?
O2 V N1 75.75(7) . . ?
O3 V N4 173.87(7) . . ?
O1 V N4 80.51(7) . . ?
O4 V N4 75.49(6) . . ?
O2 V N4 81.52(6) . . ?
N1 V N4 90.35(7) . . ?
C7 N1 N2 115.77(18) . . ?
C7 N1 V 129.21(16) . . ?
N2 N1 V 114.59(13) . . ?
C8 N2 N1 109.70(18) . . ?
C10 N3 HN3A 114.8(17) . . ?
C10 N3 HN3B 116.7(17) . . ?
HN3A N3 HN3B 114(2) . . ?
C16 N4 C24 117.5(2) . . ?
C16 N4 V 135.60(16) . . ?
C24 N4 V 106.60(14) . . ?
C2 O1 V 134.39(14) . . ?
C8 O2 V 117.92(14) . . ?
C23 O4 V 124.68(13) . . ?
C2 C1 C6 117.7(2) . . ?
C2 C1 C7 121.9(2) . . ?
C6 C1 C7 120.3(2) . . ?
O1 C2 C3 118.1(2) . . ?
O1 C2 C1 121.4(2) . . ?
C3 C2 C1 120.5(2) . . ?
C4 C3 C2 120.3(2) . . ?
C4 C3 H3 119.8 . . ?
C2 C3 H3 119.8 . . ?
C5 C4 C3 119.3(2) . . ?
C5 C4 H4 120.4 . . ?
C3 C4 H4 120.4 . . ?
C6 C5 C4 121.6(2) . . ?
C6 C5 Cl1 119.68(18) . . ?
C4 C5 Cl1 118.70(18) . . ?
C5 C6 C1 120.5(2) . . ?
C5 C6 H6 119.7 . . ?
C1 C6 H6 119.7 . . ?
N1 C7 C1 121.0(2) . . ?
N1 C7 C15 119.4(2) . . ?
C1 C7 C15 119.62(19) . . ?
O2 C8 N2 121.7(2) . . ?
O2 C8 C9 117.83(19) . . ?
N2 C8 C9 120.5(2) . . ?
C14 C9 C10 118.5(2) . . ?
C14 C9 C8 117.7(2) . . ?
C10 C9 C8 123.8(2) . . ?
N3 C10 C11 119.0(2) . . ?
N3 C10 C9 122.7(2) . . ?
C11 C10 C9 118.2(2) . . ?
C12 C11 C10 121.6(2) . . ?
C12 C11 H11 119.2 . . ?
C10 C11 H11 119.2 . . ?
C11 C12 C13 120.5(2) . . ?
C11 C12 H12 119.7 . . ?
C13 C12 H12 119.7 . . ?
C14 C13 C12 119.1(2) . . ?
C14 C13 H13 120.4 . . ?
C12 C13 H13 120.4 . . ?
C13 C14 C9 122.1(2) . . ?
C13 C14 H14 119.0 . . ?
C9 C14 H14 119.0 . . ?
C7 C15 H15A 109.5 . . ?
C7 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C7 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C7 C15 H15D 109.5 . . ?
H15A C15 H15D 141.1 . . ?
H15B C15 H15D 56.3 . . ?
H15C C15 H15D 56.3 . . ?
C7 C15 H15E 109.5 . . ?
H15A C15 H15E 56.3 . . ?
H15B C15 H15E 141.1 . . ?
H15C C15 H15E 56.3 . . ?
H15D C15 H15E 109.5 . . ?
C7 C15 H15F 109.5 . . ?
H15A C15 H15F 56.3 . . ?
H15B C15 H15F 56.3 . . ?
H15C C15 H15F 141.1 . . ?
H15D C15 H15F 109.5 . . ?
H15E C15 H15F 109.5 . . ?
N4 C16 C17 122.8(2) . . ?
N4 C16 H16 118.6 . . ?
C17 C16 H16 118.6 . . ?
C18 C17 C16 119.4(2) . . ?
C18 C17 H17 120.3 . . ?
C16 C17 H17 120.3 . . ?
C17 C18 C19 119.9(2) . . ?
C17 C18 H18 120.0 . . ?
C19 C18 H18 120.0 . . ?
C24 C19 C18 116.4(2) . . ?
C24 C19 C20 118.6(2) . . ?
C18 C19 C20 125.1(2) . . ?
C21 C20 C19 120.3(2) . . ?
C21 C20 H20 119.9 . . ?
C19 C20 H20 119.9 . . ?
C20 C21 C22 121.6(2) . . ?
C20 C21 H21 119.2 . . ?
C22 C21 H21 119.2 . . ?
C23 C22 C21 119.3(2) . . ?
C23 C22 H22 120.4 . . ?
C21 C22 H22 120.4 . . ?
O4 C23 C22 122.5(2) . . ?
O4 C23 C24 117.27(19) . . ?
C22 C23 C24 120.1(2) . . ?
N4 C24 C19 124.0(2) . . ?
N4 C24 C23 115.8(2) . . ?
C19 C24 C23 120.2(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
C6 H6 O3 0.93 2.46 3.276(3) 146.1 1_545
C15 H15B O3 0.96 2.42 3.319(3) 154.8 3_755
N3 HN3B N2 0.833(15) 2.117(19) 2.725(3) 130(2) .
N3 HN3B O3 0.833(15) 2.47(2) 2.941(3) 116.8(19) 3_755
C6 H6 O3 0.93 2.46 3.276(3) 146.1 1_545
C15 H15B O3 0.96 2.42 3.319(3) 154.8 3_755
N3 HN3B N2 0.833(15) 2.117(19) 2.725(3) 130(2) .
N3 HN3B O3 0.833(15) 2.47(2) 2.941(3) 116.8(19) 3_755

_refine_diff_density_max         0.348
_refine_diff_density_min         -0.385
_refine_diff_density_rms         0.068

