# Supplementary Material (ESI) for Dalton Transactions
# This journal is (c) The Royal Society of Chemistry 2009

data_global
_journal_name_full               'Dalton Trans.'

_journal_coden_Cambridge         0222
_journal_volume                  ?
_journal_page_first              ?
_journal_year                    ?

_publ_contact_author_name        'Surajit Chattopadhyay'
_publ_contact_author_email       SCHA8@REDIFFMAIL.COM

_publ_section_title              
;
Synthesis, structure and reactivity
of azosalophen complexes of Vanadium (IV): studies on cytotoxic properties
;
loop_
_publ_author_name
'Surajit Chattopadhyay'
'Arindam Bhattacharyya'
'Hon Man Lee.'
'Soham Mitra'
'Debprasad Patra'
;
P.Pattanayak
;
'Jahar Lal Pratihar'

# Attachment '16V.cif'

data_s1v
_database_code_depnum_ccdc_archive 'CCDC 671690'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C19 H15 N3 O4 V'
_chemical_formula_sum            'C19 H15 N3 O4 V'
_chemical_formula_weight         400.28

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

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/c'

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

_cell_length_a                   12.149(2)
_cell_length_b                   11.6449(14)
_cell_length_c                   12.0062(14)
_cell_angle_alpha                90.00
_cell_angle_beta                 102.807(2)
_cell_angle_gamma                90.00
_cell_volume                     1656.3(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.09
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.601
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             816
_exptl_absorpt_coefficient_mu    0.632
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8735
_exptl_absorpt_correction_T_max  0.9453
_exptl_absorpt_process_details   'SADABS 2.10 (Sheldrick, 2003)'

_exptl_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  'Bruker SMART APEX II'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            19714
_diffrn_reflns_av_R_equivalents  0.0824
_diffrn_reflns_av_sigmaI/netI    0.0722
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.45
_diffrn_reflns_theta_max         28.67
_reflns_number_total             4269
_reflns_number_gt                2840
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[\s^2^(Fo^2^)+(0.0430P)^2^+0.2526P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4269
_refine_ls_number_parameters     252
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0818
_refine_ls_R_factor_gt           0.0415
_refine_ls_wR_factor_ref         0.1000
_refine_ls_wR_factor_gt          0.0876
_refine_ls_goodness_of_fit_ref   1.009
_refine_ls_restrained_S_all      1.009
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
H1B H 0.418(3) 0.423(3) 0.022(3) 0.047(10) Uiso 1 1 d . . .
H1A H 0.475(3) 0.364(3) 0.118(3) 0.048(10) Uiso 1 1 d . . .
C12 C 0.40488(19) 0.43015(18) 0.35787(18) 0.0169(5) Uani 1 1 d . . .
C7 C 0.29654(19) 0.46197(19) 0.29854(18) 0.0174(5) Uani 1 1 d . . .
C8 C 0.2011(2) 0.4248(2) 0.3339(2) 0.0233(5) Uani 1 1 d . . .
H8 H 0.1280 0.4451 0.2917 0.028 Uiso 1 1 calc R . .
C9 C 0.2134(2) 0.3584(2) 0.4307(2) 0.0255(6) Uani 1 1 d . . .
H9 H 0.1486 0.3333 0.4558 0.031 Uiso 1 1 calc R . .
C10 C 0.3207(2) 0.32807(19) 0.49174(19) 0.0221(5) Uani 1 1 d . . .
H10 H 0.3284 0.2832 0.5591 0.027 Uiso 1 1 calc R . .
C11 C 0.4153(2) 0.36195(19) 0.45606(18) 0.0192(5) Uani 1 1 d . . .
H11 H 0.4879 0.3393 0.4978 0.023 Uiso 1 1 calc R . .
C13 C 0.59907(19) 0.43650(18) 0.35201(18) 0.0174(5) Uani 1 1 d . . .
H13 H 0.6112 0.3822 0.4126 0.021 Uiso 1 1 calc R . .
C14 C 0.69535(19) 0.47276(19) 0.31157(18) 0.0184(5) Uani 1 1 d . . .
C15 C 0.8012(2) 0.43646(19) 0.37549(19) 0.0217(5) Uani 1 1 d . . .
H15 H 0.8042 0.3903 0.4413 0.026 Uiso 1 1 calc R . .
C16 C 0.9001(2) 0.4658(2) 0.3455(2) 0.0247(5) Uani 1 1 d . . .
H16 H 0.9708 0.4419 0.3907 0.030 Uiso 1 1 calc R . .
C17 C 0.8947(2) 0.5317(2) 0.2470(2) 0.0251(5) Uani 1 1 d . . .
H17 H 0.9625 0.5516 0.2247 0.030 Uiso 1 1 calc R . .
C18 C 0.7934(2) 0.56814(19) 0.1823(2) 0.0217(5) Uani 1 1 d . . .
H18 H 0.7924 0.6119 0.1153 0.026 Uiso 1 1 calc R . .
C19 C 0.69102(19) 0.54221(19) 0.21269(19) 0.0183(5) Uani 1 1 d . . .
C1 C 0.18058(19) 0.62673(19) 0.04692(18) 0.0187(5) Uani 1 1 d . . .
C6 C 0.0671(2) 0.6530(2) -0.0035(2) 0.0227(5) Uani 1 1 d . . .
H6 H 0.0092 0.6258 0.0315 0.027 Uiso 1 1 calc R . .
C5 C 0.0381(2) 0.7166(2) -0.1012(2) 0.0267(6) Uani 1 1 d . . .
H5 H -0.0386 0.7350 -0.1331 0.032 Uiso 1 1 calc R . .
C4 C 0.1242(2) 0.7544(2) -0.1537(2) 0.0240(5) Uani 1 1 d . . .
H4 H 0.1049 0.7978 -0.2223 0.029 Uiso 1 1 calc R . .
C3 C 0.2349(2) 0.73001(19) -0.10844(19) 0.0197(5) Uani 1 1 d . . .
H3 H 0.2907 0.7565 -0.1465 0.024 Uiso 1 1 calc R . .
C2 C 0.26870(19) 0.66634(19) -0.00634(18) 0.0172(5) Uani 1 1 d . . .
N3 N 0.49645(16) 0.47138(15) 0.31313(15) 0.0161(4) Uani 1 1 d . . .
N2 N 0.29198(16) 0.53547(16) 0.20195(15) 0.0174(4) Uani 1 1 d . . .
N1 N 0.19366(16) 0.55841(16) 0.14378(16) 0.0204(4) Uani 1 1 d . . .
O1 O 0.59641(13) 0.58132(13) 0.14756(12) 0.0197(3) Uani 1 1 d . . .
O2 O 0.37633(13) 0.64689(13) 0.03307(12) 0.0191(3) Uani 1 1 d . . .
O3 O 0.42624(15) 0.41476(16) 0.08797(16) 0.0217(4) Uani 1 1 d . . .
O4 O 0.45735(14) 0.70451(13) 0.26423(13) 0.0224(4) Uani 1 1 d . . .
V V 0.44893(3) 0.59179(3) 0.18496(3) 0.01607(11) Uani 1 1 d . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
C12 0.0191(12) 0.0145(11) 0.0174(10) 0.0000(8) 0.0048(9) 0.0003(9)
C7 0.0200(13) 0.0174(11) 0.0159(10) 0.0016(9) 0.0063(9) 0.0017(10)
C8 0.0162(12) 0.0268(13) 0.0279(12) 0.0040(10) 0.0069(10) 0.0026(10)
C9 0.0272(14) 0.0227(12) 0.0309(13) 0.0055(11) 0.0155(12) 0.0018(11)
C10 0.0290(14) 0.0183(11) 0.0208(11) 0.0043(9) 0.0094(11) 0.0031(10)
C11 0.0209(13) 0.0177(11) 0.0186(11) 0.0016(9) 0.0032(10) 0.0056(10)
C13 0.0207(13) 0.0180(11) 0.0129(10) -0.0006(8) 0.0023(9) 0.0016(9)
C14 0.0175(12) 0.0189(11) 0.0184(11) -0.0024(9) 0.0033(10) 0.0014(10)
C15 0.0229(13) 0.0239(12) 0.0173(11) 0.0018(9) 0.0021(10) 0.0037(10)
C16 0.0172(13) 0.0281(13) 0.0268(13) 0.0004(11) 0.0004(10) 0.0027(10)
C17 0.0152(13) 0.0268(13) 0.0333(14) -0.0021(11) 0.0052(11) -0.0039(10)
C18 0.0201(13) 0.0218(12) 0.0241(12) 0.0022(9) 0.0067(10) -0.0008(10)
C19 0.0183(13) 0.0168(11) 0.0186(11) -0.0030(9) 0.0019(10) 0.0021(9)
C1 0.0197(12) 0.0192(11) 0.0181(11) 0.0023(9) 0.0061(10) 0.0024(10)
C6 0.0166(12) 0.0291(13) 0.0228(12) 0.0030(10) 0.0050(10) -0.0006(10)
C5 0.0192(13) 0.0326(14) 0.0265(13) 0.0027(11) 0.0016(11) 0.0062(11)
C4 0.0282(15) 0.0246(13) 0.0175(11) 0.0041(10) 0.0018(10) 0.0038(11)
C3 0.0225(13) 0.0197(11) 0.0176(11) 0.0001(9) 0.0059(10) 0.0001(10)
C2 0.0174(12) 0.0176(11) 0.0158(10) -0.0016(9) 0.0021(9) 0.0011(9)
N3 0.0163(11) 0.0158(9) 0.0161(9) -0.0013(8) 0.0034(8) 0.0002(8)
N2 0.0164(10) 0.0198(10) 0.0157(9) -0.0003(8) 0.0030(8) 0.0028(8)
N1 0.0186(11) 0.0220(10) 0.0205(10) 0.0015(8) 0.0044(9) 0.0022(8)
O1 0.0176(8) 0.0239(8) 0.0175(7) 0.0030(7) 0.0038(7) 0.0009(7)
O2 0.0159(9) 0.0244(8) 0.0172(8) 0.0034(7) 0.0040(7) 0.0007(7)
O3 0.0243(10) 0.0221(9) 0.0183(9) -0.0013(8) 0.0037(7) 0.0026(8)
O4 0.0244(10) 0.0204(8) 0.0230(8) 0.0011(7) 0.0063(7) 0.0018(7)
V 0.0150(2) 0.01707(19) 0.01609(18) 0.00166(16) 0.00345(14) 0.00098(17)

_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
C12 C7 1.400(3) . ?
C12 C11 1.404(3) . ?
C12 N3 1.422(3) . ?
C7 C8 1.389(3) . ?
C7 N2 1.433(3) . ?
C8 C9 1.375(3) . ?
C9 C10 1.392(3) . ?
C10 C11 1.371(3) . ?
C13 N3 1.296(3) . ?
C13 C14 1.426(3) . ?
C14 C15 1.408(3) . ?
C14 C19 1.428(3) . ?
C15 C16 1.371(3) . ?
C16 C17 1.399(3) . ?
C17 C18 1.369(3) . ?
C18 C19 1.404(3) . ?
C19 O1 1.320(3) . ?
C1 N1 1.389(3) . ?
C1 C6 1.411(3) . ?
C1 C2 1.439(3) . ?
C6 C5 1.366(3) . ?
C5 C4 1.406(3) . ?
C4 C3 1.364(3) . ?
C3 C2 1.413(3) . ?
C2 O2 1.308(3) . ?
N3 V 2.0673(18) . ?
N2 N1 1.271(3) . ?
N2 V 2.0689(19) . ?
O1 V 1.9452(15) . ?
O2 V 1.9499(15) . ?
O3 V 2.3537(17) . ?
O4 V 1.6112(16) . ?

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
C7 C12 C11 118.4(2) . . ?
C7 C12 N3 116.38(19) . . ?
C11 C12 N3 125.2(2) . . ?
C8 C7 C12 121.1(2) . . ?
C8 C7 N2 123.3(2) . . ?
C12 C7 N2 115.66(19) . . ?
C9 C8 C7 119.5(2) . . ?
C8 C9 C10 120.1(2) . . ?
C11 C10 C9 121.0(2) . . ?
C10 C11 C12 120.0(2) . . ?
N3 C13 C14 125.5(2) . . ?
C15 C14 C13 116.4(2) . . ?
C15 C14 C19 118.9(2) . . ?
C13 C14 C19 124.7(2) . . ?
C16 C15 C14 122.0(2) . . ?
C15 C16 C17 118.6(2) . . ?
C18 C17 C16 121.2(2) . . ?
C17 C18 C19 121.5(2) . . ?
O1 C19 C18 118.5(2) . . ?
O1 C19 C14 123.7(2) . . ?
C18 C19 C14 117.8(2) . . ?
N1 C1 C6 113.78(19) . . ?
N1 C1 C2 126.7(2) . . ?
C6 C1 C2 119.5(2) . . ?
C5 C6 C1 121.8(2) . . ?
C6 C5 C4 118.6(2) . . ?
C3 C4 C5 121.4(2) . . ?
C4 C3 C2 121.8(2) . . ?
O2 C2 C3 118.7(2) . . ?
O2 C2 C1 124.5(2) . . ?
C3 C2 C1 116.8(2) . . ?
C13 N3 C12 121.93(19) . . ?
C13 N3 V 124.63(15) . . ?
C12 N3 V 113.42(14) . . ?
N1 N2 C7 115.68(18) . . ?
N1 N2 V 130.81(15) . . ?
C7 N2 V 113.46(14) . . ?
N2 N1 C1 119.97(19) . . ?
C19 O1 V 127.64(14) . . ?
C2 O2 V 127.16(13) . . ?
O4 V O1 104.26(8) . . ?
O4 V O2 103.93(7) . . ?
O1 V O2 93.07(6) . . ?
O4 V N3 98.17(8) . . ?
O1 V N3 90.56(7) . . ?
O2 V N3 155.95(7) . . ?
O4 V N2 98.00(8) . . ?
O1 V N2 156.81(7) . . ?
O2 V N2 87.75(7) . . ?
N3 V N2 79.80(7) . . ?
O4 V O3 172.28(7) . . ?
O1 V O3 81.01(6) . . ?
O2 V O3 81.17(7) . . ?
N3 V O3 75.93(7) . . ?
N2 V O3 76.21(7) . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        28.67
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.379
_refine_diff_density_min         -0.380
_refine_diff_density_rms         0.075