# Electronic Supplementary Material (ESI) for Dalton Transactions
# This journal is © The Royal Society of Chemistry 2012


data_global
_journal_name_full               'Dalton Trans.'
_journal_coden_cambridge         0222
_journal_year                    ?
_journal_volume                  ?
_journal_page_first              ?
loop_
_publ_author_name
T.K.Si
M.Drew
K.K.Mukherjea
_publ_contact_author_name        'Tapan Kumar Si'
_publ_contact_author_email       tksi2002@yahoo.co.in

data_1
_database_code_depnum_ccdc_archive 'CCDC 628820'
#TrackingRef '- VO(O2)revised.cif'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H17.50 N3 O5.75 V'
_chemical_formula_weight         442.81

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'
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'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   C2/c

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

_cell_length_a                   18.367(2)
_cell_length_b                   17.309(2)
_cell_length_c                   13.316(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 108.167(16)
_cell_angle_gamma                90.00
_cell_volume                     4022.4(12)
_cell_formula_units_Z            8
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    9238
_cell_measurement_theta_min      2.55
_cell_measurement_theta_max      26.00

_exptl_crystal_description       needle
_exptl_crystal_colour            black
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.05
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.462
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1820
_exptl_absorpt_coefficient_mu    0.534
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   'ABSPACK, Oxford Diffraction Ltd'

_exptl_absorpt_correction_T_min  0.793
_exptl_absorpt_correction_T_max  1.000

_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_standards_number         n/a
_diffrn_measurement_device       'Oxford Diffaction X-Calibur 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            9238
_diffrn_reflns_av_R_equivalents  0.0419
_diffrn_reflns_av_sigmaI/netI    0.0489
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.55
_diffrn_reflns_theta_max         26.00
_reflns_number_total             3657
_reflns_number_gt                2647
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Crysalis, Oxford Diffraction'
_computing_cell_refinement       'Crysalis, Oxford Diffraction'
_computing_data_reduction        'Crysalis, Oxford Diffraction'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    PLATON(Spek,2004)

_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.

the water molecules O1W and O2W were refined with 50% occupancy.
Despite a hydrogen bond distance of 2.59 between them, the hydrogen
atoms could not be located in a difference Fourier map. Presumably
the hydrogen atom is disordered between donor and acceptor positions.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
_refine_ls_weighting_details
w=1/[\s^2^(Fo^2^)+(0.0905P)^2^+8.7665P] 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    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3657
_refine_ls_number_parameters     268
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1072
_refine_ls_R_factor_gt           0.0740
_refine_ls_wR_factor_ref         0.1905
_refine_ls_wR_factor_gt          0.1728
_refine_ls_goodness_of_fit_ref   1.106
_refine_ls_restrained_S_all      1.106
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
V1 V 0.32005(4) 0.03725(4) 0.32806(6) 0.0391(3) Uani 1 1 d . . .
N11 N 0.37447(19) 0.11763(19) 0.4515(3) 0.0347(8) Uani 1 1 d . . .
C12 C 0.4356(3) 0.1006(3) 0.5324(4) 0.0439(11) Uani 1 1 d . . .
H12 H 0.4549 0.0506 0.5378 0.053 Uiso 1 1 calc R . .
C13 C 0.4723(3) 0.1540(3) 0.6095(4) 0.0542(13) Uani 1 1 d . . .
H13 H 0.5155 0.1398 0.6646 0.065 Uiso 1 1 calc R . .
C14 C 0.4446(3) 0.2265(3) 0.6037(4) 0.0587(14) Uani 1 1 d . . .
H14 H 0.4683 0.2624 0.6555 0.070 Uiso 1 1 calc R . .
C15 C 0.3801(3) 0.2479(3) 0.5194(4) 0.0470(12) Uani 1 1 d . . .
C16 C 0.3469(2) 0.1910(2) 0.4439(3) 0.0353(9) Uani 1 1 d . . .
C17 C 0.2828(2) 0.2093(2) 0.3540(4) 0.0384(10) Uani 1 1 d . . .
C18 C 0.2543(3) 0.2858(3) 0.3402(5) 0.0507(13) Uani 1 1 d . . .
C19 C 0.1928(3) 0.3000(4) 0.2501(5) 0.0638(16) Uani 1 1 d . . .
H19 H 0.1724 0.3495 0.2368 0.077 Uiso 1 1 calc R . .
C20 C 0.1626(3) 0.2419(4) 0.1816(5) 0.0661(17) Uani 1 1 d . . .
H20 H 0.1208 0.2512 0.1220 0.079 Uiso 1 1 calc R . .
C21 C 0.1946(3) 0.1677(3) 0.2009(4) 0.0554(13) Uani 1 1 d . . .
H21 H 0.1741 0.1284 0.1527 0.066 Uiso 1 1 calc R . .
N22 N 0.2536(2) 0.1519(2) 0.2866(3) 0.0405(9) Uani 1 1 d . . .
C23 C 0.3482(4) 0.3242(3) 0.5041(6) 0.0644(16) Uani 1 1 d . . .
H23 H 0.3687 0.3620 0.5546 0.077 Uiso 1 1 calc R . .
C24 C 0.2894(4) 0.3421(3) 0.4184(6) 0.0681(17) Uani 1 1 d . . .
H24 H 0.2711 0.3925 0.4098 0.082 Uiso 1 1 calc R . .
O31 O 0.38848(16) 0.10089(17) 0.2621(2) 0.0399(7) Uani 1 1 d . . .
C32 C 0.3738(2) 0.0896(3) 0.1640(4) 0.0388(10) Uani 1 1 d . . .
N33 N 0.3180(2) 0.0436(2) 0.1171(3) 0.0470(10) Uani 1 1 d . . .
H33 H 0.3069 0.0335 0.0508 0.056 Uiso 1 1 calc R . .
O34 O 0.2774(2) 0.01169(19) 0.1774(3) 0.0514(9) Uani 1 1 d . . .
C35 C 0.4195(3) 0.1290(3) 0.1029(4) 0.0458(11) Uani 1 1 d . . .
H35A H 0.4013 0.1118 0.0300 0.055 Uiso 1 1 calc R . .
H35B H 0.4728 0.1137 0.1318 0.055 Uiso 1 1 calc R . .
C36 C 0.3463(3) 0.2531(3) 0.0993(5) 0.0571(14) Uani 1 1 d . . .
H36 H 0.3029 0.2242 0.0960 0.069 Uiso 1 1 calc R . .
C37 C 0.3419(4) 0.3324(4) 0.0977(6) 0.0778(19) Uani 1 1 d . . .
H37 H 0.2963 0.3568 0.0956 0.093 Uiso 1 1 calc R . .
C38 C 0.4047(5) 0.3754(4) 0.0992(6) 0.086(2) Uani 1 1 d . . .
H38 H 0.4011 0.4290 0.0937 0.103 Uiso 1 1 calc R . .
C39 C 0.4725(4) 0.3395(4) 0.1087(6) 0.085(2) Uani 1 1 d . . .
H39 H 0.5157 0.3690 0.1128 0.102 Uiso 1 1 calc R . .
C40 C 0.4778(3) 0.2603(4) 0.1122(5) 0.0621(15) Uani 1 1 d . . .
H40 H 0.5245 0.2366 0.1190 0.075 Uiso 1 1 calc R . .
C41 C 0.4143(3) 0.2156(3) 0.1058(4) 0.0432(11) Uani 1 1 d . . .
O2 O 0.25915(19) 0.02421(19) 0.4180(3) 0.0517(9) Uani 1 1 d . . .
O1 O 0.3861(2) -0.02579(18) 0.3736(3) 0.0581(10) Uani 1 1 d . . .
O3 O 0.2305(2) -0.0160(2) 0.3212(3) 0.0651(11) Uani 1 1 d . . .
O1W O 0.0000 0.9013(14) -0.2500 0.181(9) Uiso 0.50 2 d SP . .
O2W O -0.0860(8) 0.9900(8) -0.1785(13) 0.148(5) Uiso 0.50 1 d P . .

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
V1 0.0539(5) 0.0302(4) 0.0322(4) 0.0021(3) 0.0121(3) -0.0013(3)
N11 0.0427(19) 0.0333(18) 0.0295(19) 0.0003(15) 0.0132(15) 0.0027(15)
C12 0.047(3) 0.049(3) 0.036(3) 0.005(2) 0.0129(19) 0.007(2)
C13 0.047(3) 0.077(4) 0.034(3) -0.003(3) 0.007(2) 0.001(3)
C14 0.063(3) 0.075(4) 0.040(3) -0.022(3) 0.019(2) -0.016(3)
C15 0.056(3) 0.044(3) 0.049(3) -0.007(2) 0.027(2) -0.007(2)
C16 0.043(2) 0.039(2) 0.030(2) 0.0034(19) 0.0193(17) 0.0022(18)
C17 0.048(2) 0.035(2) 0.039(3) 0.006(2) 0.0234(19) 0.0027(19)
C18 0.059(3) 0.043(3) 0.062(3) 0.017(3) 0.036(2) 0.015(2)
C19 0.065(4) 0.061(4) 0.075(4) 0.033(3) 0.036(3) 0.028(3)
C20 0.051(3) 0.091(5) 0.058(4) 0.032(3) 0.018(3) 0.025(3)
C21 0.049(3) 0.077(4) 0.038(3) 0.014(3) 0.011(2) 0.006(3)
N22 0.0411(19) 0.047(2) 0.036(2) 0.0101(18) 0.0149(16) 0.0012(17)
C23 0.086(4) 0.043(3) 0.075(4) -0.014(3) 0.040(3) -0.002(3)
C24 0.093(4) 0.032(3) 0.094(5) 0.002(3) 0.051(4) 0.014(3)
O31 0.0473(17) 0.0447(17) 0.0281(17) -0.0026(14) 0.0122(12) -0.0019(13)
C32 0.047(2) 0.038(2) 0.033(2) 0.001(2) 0.0136(19) 0.0082(19)
N33 0.062(2) 0.049(2) 0.029(2) -0.0043(19) 0.0132(17) -0.0060(19)
O34 0.067(2) 0.0479(19) 0.038(2) -0.0060(15) 0.0143(15) -0.0171(16)
C35 0.056(3) 0.053(3) 0.033(2) -0.001(2) 0.020(2) 0.004(2)
C36 0.054(3) 0.055(3) 0.067(4) 0.007(3) 0.026(3) 0.006(2)
C37 0.093(5) 0.058(4) 0.093(5) 0.013(4) 0.044(4) 0.020(3)
C38 0.146(7) 0.042(3) 0.085(5) 0.000(3) 0.057(5) 0.000(4)
C39 0.096(5) 0.072(5) 0.102(6) -0.009(4) 0.050(4) -0.027(4)
C40 0.060(3) 0.073(4) 0.062(4) -0.003(3) 0.032(3) -0.006(3)
C41 0.050(3) 0.053(3) 0.030(2) -0.002(2) 0.0172(19) 0.001(2)
O2 0.061(2) 0.055(2) 0.0378(19) 0.0071(16) 0.0142(15) -0.0087(16)
O1 0.079(2) 0.0375(18) 0.055(2) 0.0052(16) 0.0173(18) 0.0139(16)
O3 0.078(3) 0.065(2) 0.053(2) -0.0010(19) 0.0216(19) -0.0259(19)

_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(3) . ?
V1 O3 1.864(4) . ?
V1 O2 1.890(4) . ?
V1 O34 1.963(3) . ?
V1 O31 2.062(3) . ?
V1 N11 2.148(4) . ?
V1 N22 2.305(4) . ?
N11 C12 1.324(6) . ?
N11 C16 1.360(5) . ?
C12 C13 1.390(7) . ?
C12 H12 0.9300 . ?
C13 C14 1.347(8) . ?
C13 H13 0.9300 . ?
C14 C15 1.404(8) . ?
C14 H14 0.9300 . ?
C15 C16 1.403(6) . ?
C15 C23 1.433(7) . ?
C16 C17 1.428(6) . ?
C17 N22 1.334(6) . ?
C17 C18 1.415(6) . ?
C18 C19 1.389(8) . ?
C18 C24 1.425(8) . ?
C19 C20 1.355(9) . ?
C19 H19 0.9300 . ?
C20 C21 1.402(8) . ?
C20 H20 0.9300 . ?
C21 N22 1.334(6) . ?
C21 H21 0.9300 . ?
C23 C24 1.340(9) . ?
C23 H23 0.9300 . ?
C24 H24 0.9300 . ?
O31 C32 1.264(5) . ?
C32 N33 1.294(6) . ?
C32 C35 1.502(6) . ?
N33 O34 1.372(5) . ?
N33 H33 0.8600 . ?
C35 C41 1.503(7) . ?
C35 H35A 0.9700 . ?
C35 H35B 0.9700 . ?
C36 C37 1.375(8) . ?
C36 C41 1.387(7) . ?
C36 H36 0.9300 . ?
C37 C38 1.367(9) . ?
C37 H37 0.9300 . ?
C38 C39 1.362(9) . ?
C38 H38 0.9300 . ?
C39 C40 1.376(9) . ?
C39 H39 0.9300 . ?
C40 C41 1.380(7) . ?
C40 H40 0.9300 . ?
O2 O3 1.414(5) . ?

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 O3 103.51(19) . . ?
O1 V1 O2 101.89(18) . . ?
O3 V1 O2 44.26(16) . . ?
O1 V1 O34 104.31(18) . . ?
O3 V1 O34 76.91(16) . . ?
O2 V1 O34 119.61(15) . . ?
O1 V1 O31 92.03(17) . . ?
O3 V1 O31 152.82(15) . . ?
O2 V1 O31 153.31(14) . . ?
O34 V1 O31 77.71(13) . . ?
O1 V1 N11 91.99(16) . . ?
O3 V1 N11 123.44(16) . . ?
O2 V1 N11 79.55(14) . . ?
O34 V1 N11 150.50(14) . . ?
O31 V1 N11 77.30(13) . . ?
O1 V1 N22 163.38(16) . . ?
O3 V1 N22 91.19(15) . . ?
O2 V1 N22 83.16(14) . . ?
O34 V1 N22 86.35(14) . . ?
O31 V1 N22 77.62(12) . . ?
N11 V1 N22 73.20(13) . . ?
C12 N11 C16 118.1(4) . . ?
C12 N11 V1 123.5(3) . . ?
C16 N11 V1 118.3(3) . . ?
N11 C12 C13 123.1(4) . . ?
N11 C12 H12 118.5 . . ?
C13 C12 H12 118.5 . . ?
C14 C13 C12 119.3(5) . . ?
C14 C13 H13 120.3 . . ?
C12 C13 H13 120.3 . . ?
C13 C14 C15 120.0(5) . . ?
C13 C14 H14 120.0 . . ?
C15 C14 H14 120.0 . . ?
C16 C15 C14 117.3(4) . . ?
C16 C15 C23 118.5(5) . . ?
C14 C15 C23 124.2(5) . . ?
N11 C16 C15 122.2(4) . . ?
N11 C16 C17 117.3(4) . . ?
C15 C16 C17 120.4(4) . . ?
N22 C17 C18 123.7(4) . . ?
N22 C17 C16 117.0(4) . . ?
C18 C17 C16 119.4(5) . . ?
C19 C18 C17 116.5(5) . . ?
C19 C18 C24 124.8(5) . . ?
C17 C18 C24 118.7(5) . . ?
C20 C19 C18 120.2(5) . . ?
C20 C19 H19 119.9 . . ?
C18 C19 H19 119.9 . . ?
C19 C20 C21 119.7(5) . . ?
C19 C20 H20 120.1 . . ?
C21 C20 H20 120.1 . . ?
N22 C21 C20 121.8(6) . . ?
N22 C21 H21 119.1 . . ?
C20 C21 H21 119.1 . . ?
C17 N22 C21 118.2(4) . . ?
C17 N22 V1 114.0(3) . . ?
C21 N22 V1 127.6(4) . . ?
C24 C23 C15 121.2(6) . . ?
C24 C23 H23 119.4 . . ?
C15 C23 H23 119.4 . . ?
C23 C24 C18 121.7(5) . . ?
C23 C24 H24 119.1 . . ?
C18 C24 H24 119.1 . . ?
C32 O31 V1 113.4(3) . . ?
O31 C32 N33 118.3(4) . . ?
O31 C32 C35 121.0(4) . . ?
N33 C32 C35 120.7(4) . . ?
C32 N33 O34 117.3(4) . . ?
C32 N33 H33 121.3 . . ?
O34 N33 H33 121.3 . . ?
N33 O34 V1 113.0(2) . . ?
C32 C35 C41 112.8(4) . . ?
C32 C35 H35A 109.0 . . ?
C41 C35 H35A 109.0 . . ?
C32 C35 H35B 109.0 . . ?
C41 C35 H35B 109.0 . . ?
H35A C35 H35B 107.8 . . ?
C37 C36 C41 121.1(5) . . ?
C37 C36 H36 119.5 . . ?
C41 C36 H36 119.5 . . ?
C38 C37 C36 119.9(6) . . ?
C38 C37 H37 120.1 . . ?
C36 C37 H37 120.1 . . ?
C39 C38 C37 119.7(6) . . ?
C39 C38 H38 120.1 . . ?
C37 C38 H38 120.1 . . ?
C38 C39 C40 120.7(6) . . ?
C38 C39 H39 119.6 . . ?
C40 C39 H39 119.6 . . ?
C39 C40 C41 120.5(6) . . ?
C39 C40 H40 119.7 . . ?
C41 C40 H40 119.7 . . ?
C40 C41 C36 117.9(5) . . ?
C40 C41 C35 120.1(4) . . ?
C36 C41 C35 122.0(4) . . ?
O3 O2 V1 66.9(2) . . ?
O2 O3 V1 68.9(2) . . ?

_diffrn_measured_fraction_theta_max 0.924
_diffrn_reflns_theta_full        26.00
_diffrn_measured_fraction_theta_full 0.924
_refine_diff_density_max         0.788
_refine_diff_density_min         -0.282
_refine_diff_density_rms         0.084

_publ_section_references         
;

Oxford Diffraction Ltd, Crysalis Program (2005)

Oxford Diffraction Ltd, Abspack Program (2005)

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