# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2020

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

data_compound1
_audit_block_doi                 10.5517/ccdc.csd.cc24pl2j
_database_code_depnum_ccdc_archive 'CCDC 1986947'
loop_
_audit_author_name
_audit_author_address
'Takahiro Sasamori'
;Nagoya City University
Japan
;
_audit_update_record             
;
2020-02-28 deposited with the CCDC.	2020-06-01 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         'C25 H18 N4 O2 S2 V'
_chemical_formula_sum            'C25 H18 N4 O2 S2 V'
_chemical_formula_weight         521.49

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
V V 0.3005 0.5294 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

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

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

_cell_length_a                   9.1494(3)
_cell_length_b                   14.5713(5)
_cell_length_c                   16.5995(6)
_cell_angle_alpha                90
_cell_angle_beta                 98.7354(15)
_cell_angle_gamma                90
_cell_volume                     2187.35(13)
_cell_formula_units_Z            4
_cell_measurement_temperature    103(2)
_cell_measurement_reflns_used    28040
_cell_measurement_theta_min      2.252
_cell_measurement_theta_max      24.99

_exptl_crystal_description       prism
_exptl_crystal_colour            red
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.584
_exptl_crystal_F_000             1068
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.150
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.030
_exptl_absorpt_coefficient_mu    0.678
_shelx_estimated_absorpt_T_min   0.905
_shelx_estimated_absorpt_T_max   0.980
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.905
_exptl_absorpt_correction_T_max  0.980
_exptl_absorpt_process_details   
;
 MULABS - Empirical Correction for Absorption Anisotropy.
 Blessing, R. H., Acta Cryst., A51, 33-38 (1995).
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      103(2)
_diffrn_radiation_wavelength     0.71075
_diffrn_radiation_type           MoK\a
_diffrn_source                   'rotating-anode X-ray tube'
_diffrn_measurement_device_type  'Rigaku VariMax Saturn'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 28.5714
_diffrn_reflns_number            28040
_diffrn_reflns_av_unetI/netI     0.0676
_diffrn_reflns_av_R_equivalents  0.1336
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.252
_diffrn_reflns_theta_max         24.992
_diffrn_reflns_theta_full        24.992
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             3840
_reflns_number_gt                3083
_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       CrystalClear
_computing_cell_refinement       CrysAlisPro
_computing_data_reduction        CrysAlisPro
_computing_structure_solution    'SHELXT-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Yadokari-XG 2011 (Wakita Nemoto et al., 2011)'
_computing_publication_material  
;Yadokari-XG 2011 (Wakita,Nemoto et al., 2011)
;
_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)+(0.0342P)²+17.3936P] 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         3840
_refine_ls_number_parameters     308
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1381
_refine_ls_R_factor_gt           0.1104
_refine_ls_wR_factor_ref         0.2096
_refine_ls_wR_factor_gt          0.1974
_refine_ls_goodness_of_fit_ref   1.372
_refine_ls_restrained_S_all      1.372
_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 0.81285(14) 0.18305(9) 0.41977(8) 0.0188(3) Uani 1 1 d . . . . .
O1 O 0.9559(5) 0.1664(4) 0.4857(3) 0.0232(13) Uani 1 1 d . . . . .
S1 S 0.9135(2) 0.13594(14) 0.29884(13) 0.0243(5) Uani 1 1 d . . . . .
C1 C 0.9303(8) 0.2471(6) 0.2647(5) 0.0236(18) Uani 1 1 d . . . . .
N1 N 0.8990(7) 0.3228(4) 0.2992(4) 0.0235(15) Uani 1 1 d . . . . .
N2 N 0.8450(6) 0.3102(4) 0.3730(4) 0.0191(14) Uani 1 1 d . . . . .
C2 C 0.8232(8) 0.3881(5) 0.4077(5) 0.0213(18) Uani 1 1 d . . . . .
H1 H 0.8562 0.4417 0.3832 0.026 Uiso 1 1 calc R U . . .
C3 C 0.7558(8) 0.4015(5) 0.4779(5) 0.0218(18) Uani 1 1 d . . . . .
C4 C 0.7510(8) 0.4928(6) 0.5128(5) 0.0208(17) Uani 1 1 d . . . . .
C5 C 0.8255(9) 0.5696(5) 0.4866(5) 0.0253(19) Uani 1 1 d . . . . .
H2 H 0.8840 0.5620 0.4444 0.030 Uiso 1 1 calc R U . . .
C6 C 0.8157(9) 0.6547(5) 0.5203(5) 0.0251(19) Uani 1 1 d . . . . .
H3 H 0.8650 0.7052 0.5003 0.030 Uiso 1 1 calc R U . . .
C7 C 0.7343(9) 0.6678(5) 0.5835(5) 0.0245(18) Uani 1 1 d . . . . .
H4 H 0.7290 0.7267 0.6073 0.029 Uiso 1 1 calc R U . . .
C8 C 0.6618(9) 0.5949(6) 0.6110(5) 0.0265(19) Uani 1 1 d . . . . .
H5 H 0.6060 0.6039 0.6541 0.032 Uiso 1 1 calc R U . . .
C9 C 0.6678(9) 0.5084(5) 0.5775(5) 0.0224(18) Uani 1 1 d . . . . .
C10 C 0.5950(9) 0.4320(5) 0.6070(5) 0.0261(19) Uani 1 1 d . . . . .
H6 H 0.5392 0.4415 0.6501 0.031 Uiso 1 1 calc R U . . .
C11 C 0.6019(8) 0.3470(5) 0.5765(5) 0.0233(18) Uani 1 1 d . . . . .
H7 H 0.5528 0.2980 0.5990 0.028 Uiso 1 1 calc R U . . .
C12 C 0.6820(8) 0.3293(5) 0.5108(5) 0.0201(17) Uani 1 1 d . . . . .
O2 O 0.6809(5) 0.2445(4) 0.4843(3) 0.0208(12) Uani 1 1 d . . . . .
S2 S 0.9935(2) 0.25644(15) 0.17006(13) 0.0255(5) Uani 1 1 d . . . . .
C13 C 1.0599(9) 0.3728(6) 0.1721(5) 0.029(2) Uani 1 1 d . . . . .
H8 H 0.9758 0.4151 0.1672 0.043 Uiso 1 1 calc R U . . .
H9 H 1.1149 0.3825 0.1266 0.043 Uiso 1 1 calc R U . . .
H10 H 1.1250 0.3840 0.2237 0.043 Uiso 1 1 calc R U . . .
N3 N 0.5911(6) 0.1680(4) 0.3326(4) 0.0190(14) Uani 1 1 d . . . . .
C14 C 0.5248(9) 0.2272(5) 0.2794(5) 0.0232(18) Uani 1 1 d . . . . .
H11 H 0.5735 0.2837 0.2728 0.028 Uiso 1 1 calc R U . . .
C15 C 0.3868(9) 0.2122(6) 0.2319(5) 0.0253(18) Uani 1 1 d . . . . .
H12 H 0.3421 0.2579 0.1955 0.030 Uiso 1 1 calc R U . . .
C16 C 0.3181(9) 0.1296(6) 0.2395(5) 0.0268(19) Uani 1 1 d . . . . .
H13 H 0.2245 0.1174 0.2079 0.032 Uiso 1 1 calc R U . . .
C17 C 0.3856(8) 0.0643(5) 0.2932(5) 0.0208(17) Uani 1 1 d . . . . .
C18 C 0.3220(8) -0.0232(5) 0.3056(5) 0.0202(17) Uani 1 1 d . . . . .
H14 H 0.2306 -0.0397 0.2738 0.024 Uiso 1 1 calc R U . . .
C19 C 0.3895(9) -0.0834(6) 0.3620(5) 0.0244(19) Uani 1 1 d . . . . .
H15 H 0.3442 -0.1409 0.3689 0.029 Uiso 1 1 calc R U . . .
C20 C 0.5280(8) -0.0615(5) 0.4111(5) 0.0190(17) Uani 1 1 d . . . . .
C21 C 0.6007(8) -0.1183(5) 0.4726(5) 0.0203(17) Uani 1 1 d . . . . .
H16 H 0.5586 -0.1755 0.4843 0.024 Uiso 1 1 calc R U . . .
C22 C 0.7331(8) -0.0909(5) 0.5157(5) 0.0229(18) Uani 1 1 d . . . . .
H17 H 0.7849 -0.1291 0.5568 0.028 Uiso 1 1 calc R U . . .
C23 C 0.7901(8) -0.0061(5) 0.4982(5) 0.0184(17) Uani 1 1 d . . . . .
H18 H 0.8821 0.0120 0.5286 0.022 Uiso 1 1 calc R U . . .
N4 N 0.7256(7) 0.0505(4) 0.4426(4) 0.0189(14) Uani 1 1 d . . . . .
C24 C 0.5949(8) 0.0234(5) 0.3981(5) 0.0184(17) Uani 1 1 d . . . . .
C25 C 0.5242(8) 0.0867(5) 0.3398(5) 0.0205(17) 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
V1 O1 1.591(5) . ?
V1 O2 1.949(5) . ?
V1 N2 2.047(6) . ?
V1 N4 2.145(6) . ?
V1 N3 2.316(6) . ?
V1 S1 2.431(2) . ?
S1 C1 1.730(9) . ?
C1 N1 1.296(10) . ?
C1 S2 1.760(8) . ?
N1 N2 1.402(9) . ?
N2 C2 1.301(10) . ?
C2 C3 1.413(11) . ?
C3 C12 1.406(11) . ?
C3 C4 1.453(11) . ?
C4 C5 1.414(11) . ?
C4 C9 1.426(11) . ?
C5 C6 1.369(11) . ?
C6 C7 1.389(11) . ?
C7 C8 1.367(11) . ?
C8 C9 1.382(11) . ?
C9 C10 1.422(11) . ?
C10 C11 1.343(11) . ?
C11 C12 1.426(11) . ?
C12 O2 1.310(9) . ?
S2 C13 1.799(8) . ?
N3 C14 1.315(10) . ?
N3 C25 1.347(10) . ?
C14 C15 1.401(11) . ?
C15 C16 1.372(11) . ?
C16 C17 1.383(11) . ?
C17 C25 1.420(11) . ?
C17 C18 1.430(11) . ?
C18 C19 1.360(11) . ?
C19 C20 1.434(11) . ?
C20 C21 1.401(11) . ?
C20 C24 1.411(10) . ?
C21 C22 1.369(11) . ?
C22 C23 1.388(11) . ?
C23 N4 1.311(10) . ?
N4 C24 1.365(9) . ?
C24 C25 1.420(11) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 V1 O2 101.9(3) . . ?
O1 V1 N2 104.4(3) . . ?
O2 V1 N2 85.9(2) . . ?
O1 V1 N4 91.8(3) . . ?
O2 V1 N4 92.2(2) . . ?
N2 V1 N4 163.8(2) . . ?
O1 V1 N3 164.9(3) . . ?
O2 V1 N3 80.2(2) . . ?
N2 V1 N3 90.6(2) . . ?
N4 V1 N3 73.2(2) . . ?
O1 V1 S1 98.6(2) . . ?
O2 V1 S1 158.03(18) . . ?
N2 V1 S1 81.29(19) . . ?
N4 V1 S1 95.13(18) . . ?
N3 V1 S1 82.12(16) . . ?
C1 S1 V1 94.0(3) . . ?
N1 C1 S1 128.0(6) . . ?
N1 C1 S2 117.0(6) . . ?
S1 C1 S2 115.0(5) . . ?
C1 N1 N2 114.0(6) . . ?
C2 N2 N1 111.7(6) . . ?
C2 N2 V1 125.6(5) . . ?
N1 N2 V1 122.7(5) . . ?
N2 C2 C3 126.9(7) . . ?
C12 C3 C2 120.8(7) . . ?
C12 C3 C4 119.0(7) . . ?
C2 C3 C4 119.9(7) . . ?
C5 C4 C9 116.3(7) . . ?
C5 C4 C3 123.8(7) . . ?
C9 C4 C3 119.9(7) . . ?
C6 C5 C4 121.8(8) . . ?
C5 C6 C7 120.6(8) . . ?
C8 C7 C6 119.2(8) . . ?
C7 C8 C9 121.6(8) . . ?
C8 C9 C10 121.8(8) . . ?
C8 C9 C4 120.5(7) . . ?
C10 C9 C4 117.8(7) . . ?
C11 C10 C9 122.7(8) . . ?
C10 C11 C12 121.0(8) . . ?
O2 C12 C3 123.7(7) . . ?
O2 C12 C11 116.7(7) . . ?
C3 C12 C11 119.6(7) . . ?
C12 O2 V1 130.1(5) . . ?
C1 S2 C13 102.2(4) . . ?
C14 N3 C25 117.8(7) . . ?
C14 N3 V1 128.9(5) . . ?
C25 N3 V1 113.2(5) . . ?
N3 C14 C15 124.0(8) . . ?
C16 C15 C14 118.2(8) . . ?
C15 C16 C17 119.7(8) . . ?
C16 C17 C25 117.9(7) . . ?
C16 C17 C18 123.7(7) . . ?
C25 C17 C18 118.4(7) . . ?
C19 C18 C17 121.5(7) . . ?
C18 C19 C20 121.1(7) . . ?
C21 C20 C24 117.4(7) . . ?
C21 C20 C19 124.3(7) . . ?
C24 C20 C19 118.3(7) . . ?
C22 C21 C20 119.5(7) . . ?
C21 C22 C23 118.8(7) . . ?
N4 C23 C22 124.3(7) . . ?
C23 N4 C24 117.6(7) . . ?
C23 N4 V1 123.5(5) . . ?
C24 N4 V1 119.0(5) . . ?
N4 C24 C20 122.4(7) . . ?
N4 C24 C25 116.8(7) . . ?
C20 C24 C25 120.7(7) . . ?
N3 C25 C24 117.8(7) . . ?
N3 C25 C17 122.3(7) . . ?
C24 C25 C17 119.9(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
V1 S1 C1 N1 1.4(7) . . . . ?
V1 S1 C1 S2 -176.9(4) . . . . ?
S1 C1 N1 N2 -0.2(10) . . . . ?
S2 C1 N1 N2 178.1(5) . . . . ?
C1 N1 N2 C2 176.3(7) . . . . ?
C1 N1 N2 V1 -1.7(8) . . . . ?
N1 N2 C2 C3 173.1(7) . . . . ?
V1 N2 C2 C3 -9.0(11) . . . . ?
N2 C2 C3 C12 -10.5(13) . . . . ?
N2 C2 C3 C4 174.9(8) . . . . ?
C12 C3 C4 C5 177.6(7) . . . . ?
C2 C3 C4 C5 -7.7(12) . . . . ?
C12 C3 C4 C9 -2.2(11) . . . . ?
C2 C3 C4 C9 172.5(7) . . . . ?
C9 C4 C5 C6 -1.3(11) . . . . ?
C3 C4 C5 C6 178.8(8) . . . . ?
C4 C5 C6 C7 1.7(12) . . . . ?
C5 C6 C7 C8 -1.0(12) . . . . ?
C6 C7 C8 C9 0.1(13) . . . . ?
C7 C8 C9 C10 178.7(8) . . . . ?
C7 C8 C9 C4 0.2(13) . . . . ?
C5 C4 C9 C8 0.4(11) . . . . ?
C3 C4 C9 C8 -179.7(8) . . . . ?
C5 C4 C9 C10 -178.2(7) . . . . ?
C3 C4 C9 C10 1.6(11) . . . . ?
C8 C9 C10 C11 -178.6(8) . . . . ?
C4 C9 C10 C11 0.0(13) . . . . ?
C9 C10 C11 C12 -1.1(13) . . . . ?
C2 C3 C12 O2 6.1(12) . . . . ?
C4 C3 C12 O2 -179.3(7) . . . . ?
C2 C3 C12 C11 -173.5(7) . . . . ?
C4 C3 C12 C11 1.1(11) . . . . ?
C10 C11 C12 O2 -179.1(7) . . . . ?
C10 C11 C12 C3 0.6(12) . . . . ?
C3 C12 O2 V1 19.2(11) . . . . ?
C11 C12 O2 V1 -161.2(5) . . . . ?
N1 C1 S2 C13 21.5(7) . . . . ?
S1 C1 S2 C13 -160.1(4) . . . . ?
C25 N3 C14 C15 2.2(12) . . . . ?
V1 N3 C14 C15 -177.2(6) . . . . ?
N3 C14 C15 C16 -1.9(13) . . . . ?
C14 C15 C16 C17 0.2(12) . . . . ?
C15 C16 C17 C25 1.1(12) . . . . ?
C15 C16 C17 C18 179.5(7) . . . . ?
C16 C17 C18 C19 -176.8(8) . . . . ?
C25 C17 C18 C19 1.6(11) . . . . ?
C17 C18 C19 C20 -0.3(11) . . . . ?
C18 C19 C20 C21 177.2(7) . . . . ?
C18 C19 C20 C24 -1.6(11) . . . . ?
C24 C20 C21 C22 -1.4(11) . . . . ?
C19 C20 C21 C22 179.8(7) . . . . ?
C20 C21 C22 C23 1.3(11) . . . . ?
C21 C22 C23 N4 0.0(12) . . . . ?
C22 C23 N4 C24 -1.2(11) . . . . ?
C22 C23 N4 V1 177.8(6) . . . . ?
C23 N4 C24 C20 1.0(11) . . . . ?
V1 N4 C24 C20 -178.1(5) . . . . ?
C23 N4 C24 C25 178.1(7) . . . . ?
V1 N4 C24 C25 -0.9(9) . . . . ?
C21 C20 C24 N4 0.3(11) . . . . ?
C19 C20 C24 N4 179.2(7) . . . . ?
C21 C20 C24 C25 -176.7(7) . . . . ?
C19 C20 C24 C25 2.1(11) . . . . ?
C14 N3 C25 C24 -179.1(7) . . . . ?
V1 N3 C25 C24 0.4(8) . . . . ?
C14 N3 C25 C17 -0.8(11) . . . . ?
V1 N3 C25 C17 178.7(6) . . . . ?
N4 C24 C25 N3 0.3(10) . . . . ?
C20 C24 C25 N3 177.5(7) . . . . ?
N4 C24 C25 C17 -178.0(7) . . . . ?
C20 C24 C25 C17 -0.9(11) . . . . ?
C16 C17 C25 N3 -0.8(11) . . . . ?
C18 C17 C25 N3 -179.3(7) . . . . ?
C16 C17 C25 C24 177.5(7) . . . . ?
C18 C17 C25 C24 -1.0(11) . . . . ?

_refine_diff_density_max         0.837
_refine_diff_density_min         -0.425
_refine_diff_density_rms         0.120

####################################################################### 
# 
# 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_compound3
_audit_block_doi                 10.5517/ccdc.csd.cc24pl4l
_database_code_depnum_ccdc_archive 'CCDC 1986949'
loop_
_audit_author_name
_audit_author_address
'Takahiro Sasamori'
;Nagoya City University
Japan
;
_audit_update_record             
;
2020-02-28 deposited with the CCDC.	2020-06-01 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         'C23 H18 N4 O2 S2 V'
_chemical_formula_sum            'C23 H18 N4 O2 S2 V'
_chemical_formula_weight         497.47

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'
S S 0.1246 0.1234 '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                   12.0790(2)
_cell_length_b                   9.19060(10)
_cell_length_c                   20.2738(3)
_cell_angle_alpha                90
_cell_angle_beta                 104.3594(10)
_cell_angle_gamma                90
_cell_volume                     2180.35(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    103(2)
_cell_measurement_reflns_used    34215
_cell_measurement_theta_min      2.074
_cell_measurement_theta_max      26.00

_exptl_crystal_description       prism
_exptl_crystal_colour            red
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.515
_exptl_crystal_F_000             1020
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.120
_exptl_absorpt_coefficient_mu    0.676
_shelx_estimated_absorpt_T_min   0.849
_shelx_estimated_absorpt_T_max   0.923
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.849
_exptl_absorpt_correction_T_max  0.923
_exptl_absorpt_process_details   
;
 MULABS - Empirical Correction for Absorption Anisotropy.
 Blessing, R. H., Acta Cryst., A51, 33-38 (1995).
;
_diffrn_ambient_temperature      103(2)
_diffrn_radiation_wavelength     0.71075
_diffrn_radiation_type           MoK\a
_diffrn_source                   'rotating-anode X-ray tube'
_diffrn_measurement_device_type  'Rigaku VariMax Saturn'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 28.5714
_diffrn_reflns_number            34215
_diffrn_reflns_av_unetI/netI     0.0198
_diffrn_reflns_av_R_equivalents  0.0444
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         2.074
_diffrn_reflns_theta_max         26.000
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             4277
_reflns_number_gt                3853
_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       CrystalClear
_computing_cell_refinement       CrysAlisPro
_computing_data_reduction        CrysAlisPro
_computing_structure_solution    'SHELXT-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Yadokari-XG 2011 (Wakita Nemoto et al., 2011)'
_computing_publication_material  
;Yadokari-XG 2011 (Wakita,Nemoto et al., 2011)
;
_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)+(0.0676P)²+14.9908P] 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         4277
_refine_ls_number_parameters     285
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0946
_refine_ls_R_factor_gt           0.0856
_refine_ls_wR_factor_ref         0.2076
_refine_ls_wR_factor_gt          0.1997
_refine_ls_goodness_of_fit_ref   1.085
_refine_ls_restrained_S_all      1.085
_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 0.61569(7) 0.64282(10) 0.32390(4) 0.0300(3) Uani 1 1 d . . . . .
O1 O 0.6587(3) 0.8052(4) 0.31713(17) 0.0313(8) Uani 1 1 d . . . . .
S1 S 0.79322(12) 0.53821(16) 0.38873(7) 0.0364(3) Uiso 1 1 d . . . . .
C1 C 0.7529(5) 0.5325(6) 0.4645(3) 0.0419(14) Uani 1 1 d . . . . .
S2 S 0.85814(16) 0.4606(2) 0.53255(8) 0.0569(5) Uani 1 1 d . . . . .
C2 C 0.7961(6) 0.4859(9) 0.6036(3) 0.061(2) Uani 1 1 d . . . . .
H1 H 0.7833 0.5899 0.6095 0.092 Uiso 1 1 calc R U . . .
H2 H 0.8481 0.4475 0.6450 0.092 Uiso 1 1 calc R U . . .
H3 H 0.7230 0.4340 0.5952 0.092 Uiso 1 1 calc R U . . .
N1 N 0.6576(4) 0.5763(6) 0.4768(2) 0.0480(14) Uani 1 1 d . . . . .
N2 N 0.5843(4) 0.6413(6) 0.4191(2) 0.0402(12) Uani 1 1 d . . . . .
C3 C 0.5007(5) 0.7117(7) 0.4336(3) 0.0424(15) Uani 1 1 d . . . . .
H4 H 0.4978 0.7126 0.4800 0.051 Uiso 1 1 calc R U . . .
C4 C 0.4120(4) 0.7884(7) 0.3863(2) 0.0380(14) Uani 1 1 d . . . . .
C5 C 0.3414(4) 0.8931(7) 0.4101(3) 0.0388(14) Uani 1 1 d . . . . .
C6 C 0.3613(5) 0.9372(8) 0.4790(3) 0.0464(17) Uani 1 1 d . . . . .
H5 H 0.4203 0.8917 0.5123 0.056 Uiso 1 1 calc R U . . .
C7 C 0.2972(5) 1.0442(9) 0.4985(3) 0.0497(18) Uani 1 1 d . . . . .
H6 H 0.3135 1.0724 0.5450 0.060 Uiso 1 1 calc R U . . .
C8 C 0.2081(5) 1.1127(8) 0.4512(3) 0.0461(16) Uani 1 1 d . . . . .
H7 H 0.1641 1.1868 0.4652 0.055 Uiso 1 1 calc R U . . .
C9 C 0.1854(4) 1.0709(8) 0.3842(3) 0.0425(15) Uani 1 1 d . . . . .
H8 H 0.1251 1.1166 0.3517 0.051 Uiso 1 1 calc R U . . .
C10 C 0.2503(4) 0.9615(7) 0.3627(3) 0.0383(14) Uani 1 1 d . . . . .
C11 C 0.2266(4) 0.9194(7) 0.2929(3) 0.0384(13) Uani 1 1 d . . . . .
H9 H 0.1635 0.9618 0.2611 0.046 Uiso 1 1 calc R U . . .
C12 C 0.2915(4) 0.8211(7) 0.2711(3) 0.0366(13) Uani 1 1 d . . . . .
H10 H 0.2725 0.7938 0.2245 0.044 Uiso 1 1 calc R U . . .
C13 C 0.3882(4) 0.7568(7) 0.3163(3) 0.0373(13) Uani 1 1 d . . . . .
O2 O 0.4509(3) 0.6670(5) 0.29001(18) 0.0398(10) Uani 1 1 d . . . . .
N3 N 0.5630(4) 0.4010(6) 0.3073(3) 0.0513(15) Uani 1 1 d . . . . .
C14 C 0.5314(7) 0.3150(9) 0.3527(4) 0.080(3) Uani 1 1 d . . . . .
H11 H 0.5242 0.3548 0.3946 0.096 Uiso 1 1 calc R U . . .
C15 C 0.5087(7) 0.1662(9) 0.3390(5) 0.091(4) Uani 1 1 d . . . . .
H12 H 0.4856 0.1067 0.3715 0.109 Uiso 1 1 calc R U . . .
C16 C 0.5198(6) 0.1074(8) 0.2794(5) 0.084(3) Uani 1 1 d . . . . .
H13 H 0.5055 0.0068 0.2703 0.100 Uiso 1 1 calc R U . . .
C17 C 0.5518(5) 0.1949(7) 0.2325(5) 0.061(2) Uani 1 1 d . . . . .
H14 H 0.5612 0.1560 0.1909 0.074 Uiso 1 1 calc R U . . .
C18 C 0.5705(4) 0.3432(6) 0.2476(4) 0.0459(17) Uani 1 1 d . . . . .
C19 C 0.5968(4) 0.4470(5) 0.1987(3) 0.0363(13) Uani 1 1 d . . . . .
C20 C 0.5868(4) 0.4147(7) 0.1302(3) 0.0455(16) Uani 1 1 d . . . . .
H15 H 0.5665 0.3194 0.1134 0.055 Uiso 1 1 calc R U . . .
C21 C 0.6062(4) 0.5213(7) 0.0874(3) 0.0429(15) Uani 1 1 d . . . . .
H16 H 0.5977 0.5010 0.0405 0.051 Uiso 1 1 calc R U . . .
C22 C 0.6380(5) 0.6573(7) 0.1125(3) 0.0383(13) Uani 1 1 d . . . . .
H17 H 0.6535 0.7319 0.0837 0.046 Uiso 1 1 calc R U . . .
C23 C 0.6470(4) 0.6839(6) 0.1808(3) 0.0308(11) Uani 1 1 d . . . . .
H18 H 0.6692 0.7784 0.1981 0.037 Uiso 1 1 calc R U . . .
N4 N 0.6258(3) 0.5825(5) 0.2238(2) 0.0298(9) 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
V1 O1 1.597(4) . ?
V1 O2 1.951(4) . ?
V1 N2 2.057(5) . ?
V1 N4 2.137(5) . ?
V1 N3 2.314(5) . ?
V1 S1 2.4191(16) . ?
S1 C1 1.724(7) . ?
C1 N1 1.301(9) . ?
C1 S2 1.756(5) . ?
S2 C2 1.797(8) . ?
C2 H1 0.9800 . ?
C2 H2 0.9800 . ?
C2 H3 0.9800 . ?
N1 N2 1.412(6) . ?
N2 C3 1.294(8) . ?
C3 C4 1.434(8) . ?
C3 H4 0.9500 . ?
C4 C13 1.405(7) . ?
C4 C5 1.445(9) . ?
C5 C10 1.415(8) . ?
C5 C6 1.417(8) . ?
C6 C7 1.368(10) . ?
C6 H5 0.9500 . ?
C7 C8 1.402(9) . ?
C7 H6 0.9500 . ?
C8 C9 1.372(8) . ?
C8 H7 0.9500 . ?
C9 C10 1.408(9) . ?
C9 H8 0.9500 . ?
C10 C11 1.428(7) . ?
C11 C12 1.341(9) . ?
C11 H9 0.9500 . ?
C12 C13 1.423(7) . ?
C12 H10 0.9500 . ?
C13 O2 1.319(7) . ?
N3 C14 1.338(9) . ?
N3 C18 1.346(9) . ?
C14 C15 1.408(12) . ?
C14 H11 0.9500 . ?
C15 C16 1.361(15) . ?
C15 H12 0.9500 . ?
C16 C17 1.371(12) . ?
C16 H13 0.9500 . ?
C17 C18 1.402(8) . ?
C17 H14 0.9500 . ?
C18 C19 1.466(9) . ?
C19 N4 1.357(6) . ?
C19 C20 1.396(9) . ?
C20 C21 1.366(10) . ?
C20 H15 0.9500 . ?
C21 C22 1.368(8) . ?
C21 H16 0.9500 . ?
C22 C23 1.382(7) . ?
C22 H17 0.9500 . ?
C23 N4 1.343(7) . ?
C23 H18 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 V1 O2 100.88(18) . . ?
O1 V1 N2 103.1(2) . . ?
O2 V1 N2 85.53(17) . . ?
O1 V1 N4 93.69(17) . . ?
O2 V1 N4 89.36(16) . . ?
N2 V1 N4 163.09(19) . . ?
O1 V1 N3 165.6(2) . . ?
O2 V1 N3 80.71(19) . . ?
N2 V1 N3 91.2(2) . . ?
N4 V1 N3 72.01(19) . . ?
O1 V1 S1 98.87(13) . . ?
O2 V1 S1 157.86(13) . . ?
N2 V1 S1 80.34(14) . . ?
N4 V1 S1 99.28(12) . . ?
N3 V1 S1 82.65(13) . . ?
C1 S1 V1 95.1(2) . . ?
N1 C1 S1 128.3(4) . . ?
N1 C1 S2 118.0(5) . . ?
S1 C1 S2 113.7(4) . . ?
C1 S2 C2 102.5(3) . . ?
S2 C2 H1 109.5 . . ?
S2 C2 H2 109.5 . . ?
H1 C2 H2 109.5 . . ?
S2 C2 H3 109.5 . . ?
H1 C2 H3 109.5 . . ?
H2 C2 H3 109.5 . . ?
C1 N1 N2 112.0(5) . . ?
C3 N2 N1 112.7(5) . . ?
C3 N2 V1 123.1(4) . . ?
N1 N2 V1 123.8(4) . . ?
N2 C3 C4 126.1(5) . . ?
N2 C3 H4 116.9 . . ?
C4 C3 H4 116.9 . . ?
C13 C4 C3 120.4(6) . . ?
C13 C4 C5 119.0(5) . . ?
C3 C4 C5 120.6(5) . . ?
C10 C5 C6 117.0(6) . . ?
C10 C5 C4 119.5(5) . . ?
C6 C5 C4 123.4(5) . . ?
C7 C6 C5 121.4(6) . . ?
C7 C6 H5 119.3 . . ?
C5 C6 H5 119.3 . . ?
C6 C7 C8 121.2(6) . . ?
C6 C7 H6 119.4 . . ?
C8 C7 H6 119.4 . . ?
C9 C8 C7 118.9(6) . . ?
C9 C8 H7 120.6 . . ?
C7 C8 H7 120.6 . . ?
C8 C9 C10 121.0(6) . . ?
C8 C9 H8 119.5 . . ?
C10 C9 H8 119.5 . . ?
C9 C10 C5 120.4(5) . . ?
C9 C10 C11 120.6(5) . . ?
C5 C10 C11 118.9(6) . . ?
C12 C11 C10 121.3(5) . . ?
C12 C11 H9 119.4 . . ?
C10 C11 H9 119.4 . . ?
C11 C12 C13 121.4(5) . . ?
C11 C12 H10 119.3 . . ?
C13 C12 H10 119.3 . . ?
O2 C13 C4 122.9(5) . . ?
O2 C13 C12 117.4(5) . . ?
C4 C13 C12 119.6(6) . . ?
C13 O2 V1 124.5(3) . . ?
C14 N3 C18 118.7(6) . . ?
C14 N3 V1 125.7(6) . . ?
C18 N3 V1 115.6(4) . . ?
N3 C14 C15 120.9(9) . . ?
N3 C14 H11 119.6 . . ?
C15 C14 H11 119.6 . . ?
C16 C15 C14 120.2(8) . . ?
C16 C15 H12 119.9 . . ?
C14 C15 H12 119.9 . . ?
C15 C16 C17 119.3(7) . . ?
C15 C16 H13 120.4 . . ?
C17 C16 H13 120.4 . . ?
C16 C17 C18 118.5(9) . . ?
C16 C17 H14 120.7 . . ?
C18 C17 H14 120.7 . . ?
N3 C18 C17 122.4(7) . . ?
N3 C18 C19 115.2(5) . . ?
C17 C18 C19 122.4(7) . . ?
N4 C19 C20 121.2(6) . . ?
N4 C19 C18 115.1(5) . . ?
C20 C19 C18 123.7(5) . . ?
C21 C20 C19 119.5(5) . . ?
C21 C20 H15 120.2 . . ?
C19 C20 H15 120.2 . . ?
C20 C21 C22 119.7(6) . . ?
C20 C21 H16 120.2 . . ?
C22 C21 H16 120.2 . . ?
C21 C22 C23 118.6(6) . . ?
C21 C22 H17 120.7 . . ?
C23 C22 H17 120.7 . . ?
N4 C23 C22 123.1(5) . . ?
N4 C23 H18 118.4 . . ?
C22 C23 H18 118.4 . . ?
C23 N4 C19 117.8(5) . . ?
C23 N4 V1 120.1(3) . . ?
C19 N4 V1 121.5(4) . . ?

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 S1 C1 N1 -1.4(6) . . . . ?
V1 S1 C1 S2 179.9(3) . . . . ?
N1 C1 S2 C2 -4.1(6) . . . . ?
S1 C1 S2 C2 174.7(4) . . . . ?
S1 C1 N1 N2 -3.0(8) . . . . ?
S2 C1 N1 N2 175.6(4) . . . . ?
C1 N1 N2 C3 -166.6(5) . . . . ?
C1 N1 N2 V1 7.3(7) . . . . ?
N1 N2 C3 C4 -179.7(6) . . . . ?
V1 N2 C3 C4 6.3(9) . . . . ?
N2 C3 C4 C13 19.9(9) . . . . ?
N2 C3 C4 C5 -163.7(6) . . . . ?
C13 C4 C5 C10 0.0(8) . . . . ?
C3 C4 C5 C10 -176.5(5) . . . . ?
C13 C4 C5 C6 -177.1(5) . . . . ?
C3 C4 C5 C6 6.5(8) . . . . ?
C10 C5 C6 C7 -1.8(8) . . . . ?
C4 C5 C6 C7 175.3(5) . . . . ?
C5 C6 C7 C8 1.0(9) . . . . ?
C6 C7 C8 C9 0.0(9) . . . . ?
C7 C8 C9 C10 -0.2(9) . . . . ?
C8 C9 C10 C5 -0.7(8) . . . . ?
C8 C9 C10 C11 -179.6(5) . . . . ?
C6 C5 C10 C9 1.6(8) . . . . ?
C4 C5 C10 C9 -175.6(5) . . . . ?
C6 C5 C10 C11 -179.5(5) . . . . ?
C4 C5 C10 C11 3.3(8) . . . . ?
C9 C10 C11 C12 176.3(5) . . . . ?
C5 C10 C11 C12 -2.6(8) . . . . ?
C10 C11 C12 C13 -1.4(9) . . . . ?
C3 C4 C13 O2 -6.2(8) . . . . ?
C5 C4 C13 O2 177.3(5) . . . . ?
C3 C4 C13 C12 172.5(5) . . . . ?
C5 C4 C13 C12 -3.9(8) . . . . ?
C11 C12 C13 O2 -176.5(5) . . . . ?
C11 C12 C13 C4 4.7(8) . . . . ?
C4 C13 O2 V1 -33.8(7) . . . . ?
C12 C13 O2 V1 147.5(4) . . . . ?
C18 N3 C14 C15 1.3(10) . . . . ?
V1 N3 C14 C15 -175.5(5) . . . . ?
N3 C14 C15 C16 0.6(12) . . . . ?
C14 C15 C16 C17 -0.8(11) . . . . ?
C15 C16 C17 C18 -0.9(10) . . . . ?
C14 N3 C18 C17 -3.2(9) . . . . ?
V1 N3 C18 C17 174.0(4) . . . . ?
C14 N3 C18 C19 175.4(5) . . . . ?
V1 N3 C18 C19 -7.5(6) . . . . ?
C16 C17 C18 N3 3.0(8) . . . . ?
C16 C17 C18 C19 -175.5(5) . . . . ?
N3 C18 C19 N4 8.9(7) . . . . ?
C17 C18 C19 N4 -172.5(5) . . . . ?
N3 C18 C19 C20 -167.3(5) . . . . ?
C17 C18 C19 C20 11.3(8) . . . . ?
N4 C19 C20 C21 -0.2(8) . . . . ?
C18 C19 C20 C21 175.9(5) . . . . ?
C19 C20 C21 C22 1.6(8) . . . . ?
C20 C21 C22 C23 -1.5(8) . . . . ?
C21 C22 C23 N4 -0.1(8) . . . . ?
C22 C23 N4 C19 1.5(7) . . . . ?
C22 C23 N4 V1 -170.1(4) . . . . ?
C20 C19 N4 C23 -1.4(7) . . . . ?
C18 C19 N4 C23 -177.7(4) . . . . ?
C20 C19 N4 V1 170.1(4) . . . . ?
C18 C19 N4 V1 -6.2(6) . . . . ?

_refine_diff_density_max         2.861
_refine_diff_density_min         -1.958
_refine_diff_density_rms         0.143

####################################################################### 
# 
# 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_compound2
_audit_block_doi                 10.5517/ccdc.csd.cc24pl3k
_database_code_depnum_ccdc_archive 'CCDC 1986948'
loop_
_audit_author_name
_audit_author_address
'Takahiro Sasamori'
;Nagoya City University
Japan
;
_audit_update_record             
;
2020-02-28 deposited with the CCDC.	2020-06-01 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         'C31 H28 Cl N5 O2 S2 V'
_chemical_formula_sum            'C31 H28 Cl N5 O2 S2 V'
_chemical_formula_weight         653.09

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'
S S 0.1246 0.1234 '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'
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                   9.2915(2)
_cell_length_b                   12.4720(2)
_cell_length_c                   14.3887(3)
_cell_angle_alpha                66.4449(8)
_cell_angle_beta                 80.6708(12)
_cell_angle_gamma                71.2920(11)
_cell_volume                     1446.62(5)
_cell_formula_units_Z            2
_cell_measurement_temperature    103(2)
_cell_measurement_reflns_used    24489
_cell_measurement_theta_min      2.316
_cell_measurement_theta_max      25.999

_exptl_crystal_description       prism
_exptl_crystal_colour            red
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.499
_exptl_crystal_F_000             674
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.120
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.080
_exptl_absorpt_coefficient_mu    0.619
_shelx_estimated_absorpt_T_min   0.929
_shelx_estimated_absorpt_T_max   0.952
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.929
_exptl_absorpt_correction_T_max  0.952
_exptl_absorpt_process_details   
;
 MULABS - Empirical Correction for Absorption Anisotropy.
 Blessing, R. H., Acta Cryst., A51, 33-38 (1995).
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      103(2)
_diffrn_radiation_wavelength     0.71075
_diffrn_radiation_type           MoK\a
_diffrn_source                   'rotating-anode X-ray tube'
_diffrn_measurement_device_type  'Rigaku VariMax Saturn'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 28.5714
_diffrn_reflns_number            24489
_diffrn_reflns_av_unetI/netI     0.0346
_diffrn_reflns_av_R_equivalents  0.0553
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.316
_diffrn_reflns_theta_max         25.999
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             5649
_reflns_number_gt                4899
_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       CrystalClear
_computing_cell_refinement       CrysAlisPro
_computing_data_reduction        CrysAlisPro
_computing_structure_solution    'SHELXT-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Yadokari-XG 2011 (Wakita Nemoto et al., 2011)'
_computing_publication_material  
;Yadokari-XG 2011 (Wakita,Nemoto et al., 2011)
;
_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)+(0.0269P)²+2.8984P] 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         5649
_refine_ls_number_parameters     381
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0622
_refine_ls_R_factor_gt           0.0502
_refine_ls_wR_factor_ref         0.1129
_refine_ls_wR_factor_gt          0.1038
_refine_ls_goodness_of_fit_ref   1.197
_refine_ls_restrained_S_all      1.197
_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 0.63938(6) 0.37044(4) 0.36626(4) 0.01487(13) Uani 1 1 d . . . . .
O1 O 0.5326(2) 0.50523(18) 0.35165(16) 0.0193(5) Uani 1 1 d . . . . .
S1 S 0.83247(8) 0.36118(7) 0.46483(6) 0.01790(17) Uani 1 1 d . . . . .
C1 C 0.9487(3) 0.4142(3) 0.3599(2) 0.0187(6) Uani 1 1 d . . . . .
N1 N 0.9354(3) 0.4289(2) 0.26720(19) 0.0185(5) Uani 1 1 d . . . . .
N2 N 0.8079(3) 0.3983(2) 0.25442(18) 0.0166(5) Uani 1 1 d . . . . .
C2 C 0.8078(3) 0.3948(3) 0.1650(2) 0.0173(6) Uani 1 1 d . . . . .
H1 H 0.8910 0.4124 0.1197 0.021 Uiso 1 1 calc R U . . .
C3 C 0.6969(3) 0.3677(3) 0.1284(2) 0.0175(6) Uani 1 1 d . . . . .
C4 C 0.7176(4) 0.3686(3) 0.0291(2) 0.0197(6) Uani 1 1 d . . . . .
H2 H 0.8064 0.3854 -0.0094 0.024 Uiso 1 1 calc R U . . .
C5 C 0.6157(4) 0.3463(3) -0.0146(2) 0.0204(6) Uani 1 1 d . . . . .
H3 H 0.6355 0.3462 -0.0815 0.024 Uiso 1 1 calc R U . . .
C6 C 0.4805(3) 0.3234(3) 0.0400(2) 0.0185(6) Uani 1 1 d . . . . .
C7 C 0.4606(3) 0.3176(3) 0.1402(2) 0.0180(6) Uani 1 1 d . . . . .
H4 H 0.3725 0.2989 0.1785 0.022 Uiso 1 1 calc R U . . .
C8 C 0.5654(3) 0.3383(3) 0.1860(2) 0.0161(6) Uani 1 1 d . . . . .
O2 O 0.5395(2) 0.32923(19) 0.28080(15) 0.0176(4) Uani 1 1 d . . . . .
S2 S 1.10078(9) 0.44583(7) 0.39241(6) 0.02133(18) Uani 1 1 d . . . . .
C9 C 1.1925(3) 0.5164(3) 0.2712(2) 0.0211(6) Uani 1 1 d . . . . .
H5 H 1.3020 0.4988 0.2806 0.025 Uiso 1 1 calc R U . . .
H6 H 1.1832 0.4808 0.2228 0.025 Uiso 1 1 calc R U . . .
C10 C 1.1221(3) 0.6519(3) 0.2281(2) 0.0199(6) Uani 1 1 d . . . . .
C11 C 1.1817(4) 0.7297(3) 0.2475(2) 0.0236(7) Uani 1 1 d . . . . .
H7 H 1.2697 0.6971 0.2866 0.028 Uiso 1 1 calc R U . . .
C12 C 1.1136(4) 0.8548(3) 0.2100(2) 0.0254(7) Uani 1 1 d . . . . .
H8 H 1.1559 0.9079 0.2219 0.031 Uiso 1 1 calc R U . . .
C13 C 0.9835(4) 0.9013(3) 0.1552(2) 0.0243(7) Uani 1 1 d . . . . .
C14 C 0.9249(4) 0.8257(3) 0.1335(2) 0.0243(7) Uani 1 1 d . . . . .
H9 H 0.8372 0.8586 0.0942 0.029 Uiso 1 1 calc R U . . .
C15 C 0.9949(3) 0.7018(3) 0.1696(2) 0.0207(6) Uani 1 1 d . . . . .
H10 H 0.9554 0.6498 0.1540 0.025 Uiso 1 1 calc R U . . .
Cl1 Cl 0.88989(10) 1.05666(8) 0.11362(7) 0.0349(2) Uani 1 1 d . . . . .
N3 N 0.7576(3) 0.1606(2) 0.41577(19) 0.0177(5) Uani 1 1 d . . . . .
C16 C 0.8757(4) 0.1016(3) 0.3731(2) 0.0225(7) Uani 1 1 d . . . . .
H11 H 0.9298 0.1479 0.3182 0.027 Uiso 1 1 calc R U . . .
C17 C 0.9251(4) -0.0256(3) 0.4048(2) 0.0253(7) Uani 1 1 d . . . . .
H12 H 1.0110 -0.0641 0.3720 0.030 Uiso 1 1 calc R U . . .
C18 C 0.8483(4) -0.0938(3) 0.4834(3) 0.0244(7) Uani 1 1 d . . . . .
H13 H 0.8801 -0.1802 0.5057 0.029 Uiso 1 1 calc R U . . .
C19 C 0.7218(4) -0.0348(3) 0.5310(2) 0.0213(7) Uani 1 1 d . . . . .
C20 C 0.6326(4) -0.0977(3) 0.6124(3) 0.0258(7) Uani 1 1 d . . . . .
H14 H 0.6578 -0.1841 0.6367 0.031 Uiso 1 1 calc R U . . .
C21 C 0.5125(4) -0.0356(3) 0.6552(2) 0.0249(7) Uani 1 1 d . . . . .
H15 H 0.4546 -0.0792 0.7092 0.030 Uiso 1 1 calc R U . . .
C22 C 0.4712(3) 0.0945(3) 0.6210(2) 0.0203(6) Uani 1 1 d . . . . .
C23 C 0.3474(4) 0.1632(3) 0.6630(2) 0.0251(7) Uani 1 1 d . . . . .
H16 H 0.2877 0.1235 0.7181 0.030 Uiso 1 1 calc R U . . .
C24 C 0.3136(4) 0.2875(3) 0.6240(2) 0.0227(7) Uani 1 1 d . . . . .
H17 H 0.2318 0.3349 0.6526 0.027 Uiso 1 1 calc R U . . .
C25 C 0.4009(3) 0.3442(3) 0.5413(2) 0.0189(6) Uani 1 1 d . . . . .
H18 H 0.3758 0.4307 0.5143 0.023 Uiso 1 1 calc R U . . .
N4 N 0.5173(3) 0.2825(2) 0.49905(18) 0.0161(5) Uani 1 1 d . . . . .
C26 C 0.5542(3) 0.1585(3) 0.5394(2) 0.0168(6) Uani 1 1 d . . . . .
C27 C 0.6824(3) 0.0930(3) 0.4947(2) 0.0176(6) Uani 1 1 d . . . . .
N5 N 0.3720(3) 0.3097(2) -0.0052(2) 0.0213(6) Uani 1 1 d . . . . .
C28 C 0.2260(4) 0.2979(3) 0.0477(3) 0.0278(7) Uani 1 1 d . . . . .
H19 H 0.1482 0.3287 -0.0034 0.033 Uiso 1 1 calc R U . . .
H20 H 0.1954 0.3503 0.0883 0.033 Uiso 1 1 calc R U . . .
C29 C 0.2268(5) 0.1690(4) 0.1173(3) 0.0395(9) Uani 1 1 d . . . . .
H21 H 0.2488 0.1175 0.0773 0.059 Uiso 1 1 calc R U . . .
H22 H 0.1270 0.1695 0.1523 0.059 Uiso 1 1 calc R U . . .
H23 H 0.3050 0.1367 0.1675 0.059 Uiso 1 1 calc R U . . .
C30 C 0.4022(4) 0.2982(3) -0.1043(2) 0.0231(7) Uani 1 1 d . . . . .
H24 H 0.4544 0.3592 -0.1498 0.028 Uiso 1 1 calc R U . . .
H25 H 0.3040 0.3171 -0.1341 0.028 Uiso 1 1 calc R U . . .
C31 C 0.4984(4) 0.1729(3) -0.0999(3) 0.0297(8) Uani 1 1 d . . . . .
H26 H 0.5946 0.1522 -0.0684 0.044 Uiso 1 1 calc R U . . .
H27 H 0.5192 0.1727 -0.1688 0.044 Uiso 1 1 calc R U . . .
H28 H 0.4438 0.1126 -0.0596 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 O1 1.603(2) . ?
V1 O2 1.954(2) . ?
V1 N2 2.061(2) . ?
V1 N4 2.135(2) . ?
V1 N3 2.342(2) . ?
V1 S1 2.4093(9) . ?
S1 C1 1.736(3) . ?
C1 N1 1.293(4) . ?
C1 S2 1.759(3) . ?
N1 N2 1.414(3) . ?
N2 C2 1.306(4) . ?
C2 C3 1.412(4) . ?
C2 H1 0.9500 . ?
C3 C4 1.407(4) . ?
C3 C8 1.424(4) . ?
C4 C5 1.367(4) . ?
C4 H2 0.9500 . ?
C5 C6 1.417(4) . ?
C5 H3 0.9500 . ?
C6 N5 1.371(4) . ?
C6 C7 1.398(4) . ?
C7 C8 1.399(4) . ?
C7 H4 0.9500 . ?
C8 O2 1.312(4) . ?
S2 C9 1.821(3) . ?
C9 C10 1.501(4) . ?
C9 H5 0.9900 . ?
C9 H6 0.9900 . ?
C10 C15 1.388(4) . ?
C10 C11 1.393(4) . ?
C11 C12 1.389(5) . ?
C11 H7 0.9500 . ?
C12 C13 1.383(5) . ?
C12 H8 0.9500 . ?
C13 C14 1.379(5) . ?
C13 Cl1 1.741(3) . ?
C14 C15 1.379(5) . ?
C14 H9 0.9500 . ?
C15 H10 0.9500 . ?
N3 C16 1.322(4) . ?
N3 C27 1.357(4) . ?
C16 C17 1.399(5) . ?
C16 H11 0.9500 . ?
C17 C18 1.368(5) . ?
C17 H12 0.9500 . ?
C18 C19 1.407(5) . ?
C18 H13 0.9500 . ?
C19 C27 1.404(4) . ?
C19 C20 1.429(5) . ?
C20 C21 1.352(5) . ?
C20 H14 0.9500 . ?
C21 C22 1.429(4) . ?
C21 H15 0.9500 . ?
C22 C26 1.400(4) . ?
C22 C23 1.407(5) . ?
C23 C24 1.366(5) . ?
C23 H16 0.9500 . ?
C24 C25 1.398(4) . ?
C24 H17 0.9500 . ?
C25 N4 1.326(4) . ?
C25 H18 0.9500 . ?
N4 C26 1.362(4) . ?
C26 C27 1.431(4) . ?
N5 C30 1.463(4) . ?
N5 C28 1.465(4) . ?
C28 C29 1.514(5) . ?
C28 H19 0.9900 . ?
C28 H20 0.9900 . ?
C29 H21 0.9800 . ?
C29 H22 0.9800 . ?
C29 H23 0.9800 . ?
C30 C31 1.513(5) . ?
C30 H24 0.9900 . ?
C30 H25 0.9900 . ?
C31 H26 0.9800 . ?
C31 H27 0.9800 . ?
C31 H28 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
O1 V1 O2 100.57(10) . . ?
O1 V1 N2 104.05(10) . . ?
O2 V1 N2 88.94(9) . . ?
O1 V1 N4 94.62(10) . . ?
O2 V1 N4 91.86(9) . . ?
N2 V1 N4 160.85(10) . . ?
O1 V1 N3 167.70(10) . . ?
O2 V1 N3 79.14(9) . . ?
N2 V1 N3 88.25(9) . . ?
N4 V1 N3 73.14(9) . . ?
O1 V1 S1 98.87(8) . . ?
O2 V1 S1 159.73(7) . . ?
N2 V1 S1 80.81(7) . . ?
N4 V1 S1 92.25(7) . . ?
N3 V1 S1 83.09(6) . . ?
C1 S1 V1 94.29(11) . . ?
N1 C1 S1 127.7(2) . . ?
N1 C1 S2 120.4(2) . . ?
S1 C1 S2 111.89(17) . . ?
C1 N1 N2 113.1(2) . . ?
C2 N2 N1 112.9(2) . . ?
C2 N2 V1 125.3(2) . . ?
N1 N2 V1 121.76(18) . . ?
N2 C2 C3 126.9(3) . . ?
N2 C2 H1 116.6 . . ?
C3 C2 H1 116.6 . . ?
C4 C3 C2 118.2(3) . . ?
C4 C3 C8 117.6(3) . . ?
C2 C3 C8 124.2(3) . . ?
C5 C4 C3 123.0(3) . . ?
C5 C4 H2 118.5 . . ?
C3 C4 H2 118.5 . . ?
C4 C5 C6 119.8(3) . . ?
C4 C5 H3 120.1 . . ?
C6 C5 H3 120.1 . . ?
N5 C6 C7 121.4(3) . . ?
N5 C6 C5 120.6(3) . . ?
C7 C6 C5 118.0(3) . . ?
C6 C7 C8 122.5(3) . . ?
C6 C7 H4 118.8 . . ?
C8 C7 H4 118.8 . . ?
O2 C8 C7 118.7(3) . . ?
O2 C8 C3 122.3(3) . . ?
C7 C8 C3 119.0(3) . . ?
C8 O2 V1 131.70(19) . . ?
C1 S2 C9 104.41(15) . . ?
C10 C9 S2 111.3(2) . . ?
C10 C9 H5 109.4 . . ?
S2 C9 H5 109.4 . . ?
C10 C9 H6 109.4 . . ?
S2 C9 H6 109.4 . . ?
H5 C9 H6 108.0 . . ?
C15 C10 C11 118.7(3) . . ?
C15 C10 C9 120.6(3) . . ?
C11 C10 C9 120.6(3) . . ?
C12 C11 C10 120.5(3) . . ?
C12 C11 H7 119.8 . . ?
C10 C11 H7 119.8 . . ?
C13 C12 C11 119.3(3) . . ?
C13 C12 H8 120.3 . . ?
C11 C12 H8 120.3 . . ?
C14 C13 C12 120.8(3) . . ?
C14 C13 Cl1 118.9(3) . . ?
C12 C13 Cl1 120.2(3) . . ?
C13 C14 C15 119.3(3) . . ?
C13 C14 H9 120.3 . . ?
C15 C14 H9 120.3 . . ?
C14 C15 C10 121.2(3) . . ?
C14 C15 H10 119.4 . . ?
C10 C15 H10 119.4 . . ?
C16 N3 C27 117.6(3) . . ?
C16 N3 V1 129.4(2) . . ?
C27 N3 V1 112.77(19) . . ?
N3 C16 C17 123.3(3) . . ?
N3 C16 H11 118.4 . . ?
C17 C16 H11 118.4 . . ?
C18 C17 C16 119.2(3) . . ?
C18 C17 H12 120.4 . . ?
C16 C17 H12 120.4 . . ?
C17 C18 C19 119.4(3) . . ?
C17 C18 H13 120.3 . . ?
C19 C18 H13 120.3 . . ?
C27 C19 C18 117.1(3) . . ?
C27 C19 C20 119.3(3) . . ?
C18 C19 C20 123.6(3) . . ?
C21 C20 C19 120.7(3) . . ?
C21 C20 H14 119.6 . . ?
C19 C20 H14 119.6 . . ?
C20 C21 C22 121.3(3) . . ?
C20 C21 H15 119.4 . . ?
C22 C21 H15 119.4 . . ?
C26 C22 C23 117.4(3) . . ?
C26 C22 C21 119.1(3) . . ?
C23 C22 C21 123.4(3) . . ?
C24 C23 C22 119.6(3) . . ?
C24 C23 H16 120.2 . . ?
C22 C23 H16 120.2 . . ?
C23 C24 C25 119.2(3) . . ?
C23 C24 H17 120.4 . . ?
C25 C24 H17 120.4 . . ?
N4 C25 C24 122.9(3) . . ?
N4 C25 H18 118.5 . . ?
C24 C25 H18 118.5 . . ?
C25 N4 C26 118.1(3) . . ?
C25 N4 V1 122.5(2) . . ?
C26 N4 V1 119.34(19) . . ?
N4 C26 C22 122.7(3) . . ?
N4 C26 C27 117.5(3) . . ?
C22 C26 C27 119.8(3) . . ?
N3 C27 C19 123.4(3) . . ?
N3 C27 C26 116.8(3) . . ?
C19 C27 C26 119.8(3) . . ?
C6 N5 C30 121.2(3) . . ?
C6 N5 C28 120.7(3) . . ?
C30 N5 C28 118.0(3) . . ?
N5 C28 C29 114.5(3) . . ?
N5 C28 H19 108.6 . . ?
C29 C28 H19 108.6 . . ?
N5 C28 H20 108.6 . . ?
C29 C28 H20 108.6 . . ?
H19 C28 H20 107.6 . . ?
C28 C29 H21 109.5 . . ?
C28 C29 H22 109.5 . . ?
H21 C29 H22 109.5 . . ?
C28 C29 H23 109.5 . . ?
H21 C29 H23 109.5 . . ?
H22 C29 H23 109.5 . . ?
N5 C30 C31 113.6(3) . . ?
N5 C30 H24 108.8 . . ?
C31 C30 H24 108.8 . . ?
N5 C30 H25 108.8 . . ?
C31 C30 H25 108.8 . . ?
H24 C30 H25 107.7 . . ?
C30 C31 H26 109.5 . . ?
C30 C31 H27 109.5 . . ?
H26 C31 H27 109.5 . . ?
C30 C31 H28 109.5 . . ?
H26 C31 H28 109.5 . . ?
H27 C31 H28 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 S1 C1 N1 -10.3(3) . . . . ?
V1 S1 C1 S2 171.13(14) . . . . ?
S1 C1 N1 N2 1.0(4) . . . . ?
S2 C1 N1 N2 179.46(19) . . . . ?
C1 N1 N2 C2 -169.9(3) . . . . ?
C1 N1 N2 V1 12.5(3) . . . . ?
N1 N2 C2 C3 -179.8(3) . . . . ?
V1 N2 C2 C3 -2.3(4) . . . . ?
N2 C2 C3 C4 -180.0(3) . . . . ?
N2 C2 C3 C8 -0.5(5) . . . . ?
C2 C3 C4 C5 -178.5(3) . . . . ?
C8 C3 C4 C5 2.0(4) . . . . ?
C3 C4 C5 C6 1.3(5) . . . . ?
C4 C5 C6 N5 175.2(3) . . . . ?
C4 C5 C6 C7 -3.6(4) . . . . ?
N5 C6 C7 C8 -176.2(3) . . . . ?
C5 C6 C7 C8 2.6(4) . . . . ?
C6 C7 C8 O2 -178.9(3) . . . . ?
C6 C7 C8 C3 0.7(4) . . . . ?
C4 C3 C8 O2 176.7(3) . . . . ?
C2 C3 C8 O2 -2.8(5) . . . . ?
C4 C3 C8 C7 -3.0(4) . . . . ?
C2 C3 C8 C7 177.6(3) . . . . ?
C7 C8 O2 V1 -170.9(2) . . . . ?
C3 C8 O2 V1 9.5(4) . . . . ?
N1 C1 S2 C9 7.9(3) . . . . ?
S1 C1 S2 C9 -173.36(16) . . . . ?
C1 S2 C9 C10 88.2(2) . . . . ?
S2 C9 C10 C15 -86.3(3) . . . . ?
S2 C9 C10 C11 92.7(3) . . . . ?
C15 C10 C11 C12 0.9(5) . . . . ?
C9 C10 C11 C12 -178.1(3) . . . . ?
C10 C11 C12 C13 1.6(5) . . . . ?
C11 C12 C13 C14 -3.0(5) . . . . ?
C11 C12 C13 Cl1 176.4(2) . . . . ?
C12 C13 C14 C15 1.9(5) . . . . ?
Cl1 C13 C14 C15 -177.5(2) . . . . ?
C13 C14 C15 C10 0.7(5) . . . . ?
C11 C10 C15 C14 -2.1(5) . . . . ?
C9 C10 C15 C14 176.9(3) . . . . ?
C27 N3 C16 C17 0.6(5) . . . . ?
V1 N3 C16 C17 -173.0(2) . . . . ?
N3 C16 C17 C18 0.3(5) . . . . ?
C16 C17 C18 C19 -0.2(5) . . . . ?
C17 C18 C19 C27 -0.6(5) . . . . ?
C17 C18 C19 C20 178.8(3) . . . . ?
C27 C19 C20 C21 -0.9(5) . . . . ?
C18 C19 C20 C21 179.7(3) . . . . ?
C19 C20 C21 C22 -0.1(5) . . . . ?
C20 C21 C22 C26 1.9(5) . . . . ?
C20 C21 C22 C23 180.0(3) . . . . ?
C26 C22 C23 C24 -0.3(5) . . . . ?
C21 C22 C23 C24 -178.4(3) . . . . ?
C22 C23 C24 C25 1.4(5) . . . . ?
C23 C24 C25 N4 -0.7(5) . . . . ?
C24 C25 N4 C26 -1.1(4) . . . . ?
C24 C25 N4 V1 175.4(2) . . . . ?
C25 N4 C26 C22 2.2(4) . . . . ?
V1 N4 C26 C22 -174.4(2) . . . . ?
C25 N4 C26 C27 -178.5(3) . . . . ?
V1 N4 C26 C27 4.9(3) . . . . ?
C23 C22 C26 N4 -1.5(4) . . . . ?
C21 C22 C26 N4 176.6(3) . . . . ?
C23 C22 C26 C27 179.2(3) . . . . ?
C21 C22 C26 C27 -2.6(4) . . . . ?
C16 N3 C27 C19 -1.5(4) . . . . ?
V1 N3 C27 C19 173.2(2) . . . . ?
C16 N3 C27 C26 -179.6(3) . . . . ?
V1 N3 C27 C26 -5.0(3) . . . . ?
C18 C19 C27 N3 1.5(4) . . . . ?
C20 C19 C27 N3 -177.9(3) . . . . ?
C18 C19 C27 C26 179.6(3) . . . . ?
C20 C19 C27 C26 0.1(4) . . . . ?
N4 C26 C27 N3 0.5(4) . . . . ?
C22 C26 C27 N3 179.8(3) . . . . ?
N4 C26 C27 C19 -177.7(3) . . . . ?
C22 C26 C27 C19 1.6(4) . . . . ?
C7 C6 N5 C30 -171.0(3) . . . . ?
C5 C6 N5 C30 10.2(4) . . . . ?
C7 C6 N5 C28 4.7(4) . . . . ?
C5 C6 N5 C28 -174.0(3) . . . . ?
C6 N5 C28 C29 -85.7(4) . . . . ?
C30 N5 C28 C29 90.2(4) . . . . ?
C6 N5 C30 C31 77.5(4) . . . . ?
C28 N5 C30 C31 -98.4(3) . . . . ?

_refine_diff_density_max         0.407
_refine_diff_density_min         -0.303
_refine_diff_density_rms         0.075

