Dioxido{1-[(phen­yl)(2-pyrid­yl)methyl­ene]-4-(p-tol­yl)thio­semicarbazonato}vanadium(V) dimethyl sulfoxide solvate

Mendes, I.C.; Speziali, N.L.; Beraldo, H.

doi:10.1107/S1600536807038275

Dioxido{1-[(phenyl)(2-pyridyl)methylene]-4-(p-tolyl)thiosemicarbazonato}vanadium(V) dimethyl sulfoxide solvate

I. C. Mendes, N. L. Speziali and H. Beraldo

In the title compound, [V(C₂₀H₁₇N₄S)O₂]·C₂H₆OS, the organic ligand coordinates the metal atom in a tridentate manner via its azomethine nitrogen, thiolate sulfur and pyridyl (py) nitrogen atoms, resulting in two five-membered chelate rings. To match the steric requirements of coordination through the N_py-N-S chelating system, the 1-[(2-pyridyl)(phenyl)methylene]-4-(p-tolyl)thiosemicarbazonate ligand adopts a configuration different to that of the parent thiosemicarbazone. The V atom shows a distorted trigonal-bipyramidal coordination geometry.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807038275/gk2096sup1.cif Contains datablocks I, global
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536807038275/gk2096Isup2.hkl Contains datablock I

CCDC reference: 660145

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Key indicators

Single-crystal X-ray study
T = 298 K
Mean (C-C) = 0.007 Å
R factor = 0.059
wR factor = 0.165
Data-to-parameter ratio = 15.3

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for          V
PLAT244_ALERT_4_C Low   'Solvent' Ueq as Compared to Neighbors for        S2A
PLAT341_ALERT_3_C Low Bond Precision on C-C Bonds (x 1000) Ang ...          7
PLAT380_ALERT_4_C Check Incorrectly? Oriented X(sp2)-Methyl Moiety        C15
PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........          6

Alert level G
PLAT794_ALERT_5_G Check Predicted Bond Valency for V           (4)       4.94

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   5 ALERT level C = Check and explain
   1 ALERT level G = General alerts; check

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   1 ALERT type 2 Indicator that the structure model may be wrong or deficient
   1 ALERT type 3 Indicator that the structure quality may be low
   3 ALERT type 4 Improvement, methodology, query or suggestion
   1 ALERT type 5 Informative message, check

Comment top

Thiosemicarbazones and their metal complexes are an important class of compounds with a wide range of pharmacological applications (Beraldo & Gambino, 2004). Vanadium complexes were found to present antimicrobial, antitumor and insulin-enhancing effects (Baran, 2000; Ahmad et al., 2006). Here we report the crystal strucuture of dioxovanadium(V) complex with 2-benzoylpyridine N(4)-(p-tolyl)thiosemicarbazone, [VO₂(2Bz4pT)]·DMSO. 2-Benzoylpyridine N(4)-(p-tolyl)thiosemicarbazone (H2Bz4pT), crystallizes as the ZE isomer, where Z and E refer to the configuration around C7=N2 and C8—N3 bonds, respectively (Mendes et al., 2006). In the title complex, to match the steric requirements of coordination through the N_py—N—S chelating system, the deprotonated ligand adopts the EZ configuration (Fig. 1). The C8—N3 bond length changes from 1.361 (3) Å in the free base to 1.322 (5) Å in the complex due to deprotonation of N3 and formation of a new predominantly double bond. In turn, the C8—S1 bond changes from 1.653 (3) Å in H2Bz4pT to 1.738 (4) Å in the complex, in agreement with deprotonation at N3 and formation of a thiolate bond. Deprotonation of the ligand and subsequent coordination to the metal center influences also bond angles. Hence, the N2—N3—C8 bond angle changes from 120.5 (2)° in the free base to 112.1 (3)° in the complex, and N3—C8—S angle changes from 117.9 (2)° in the ligand to 125.0 (3)° in the complex. The atomic arrangement around the vanadium ion has a distorted trigonal bipyramidal geometry (Fig. 2): the interatomic angles in the equatorial plane are in the 111.1 (3)–127.1 (2)° range and the axial angle N1—V—S1 is 151.2 (1)°. The V=O bond distances of 1.606 (4) Å and 1.599 (4) Å are shorter than in the other 2-pyridine thiosemicarbazones vanadium complexes recently published (1.623–1.608 Å; Philip et al., 2005; Sreekanth et al., 2003). A single hydrogen bond was observed between N4—H4B and the oxygen atom from the DMSO molecule. The antifungal activities of the free base and the vanadium complex were evalueted against Candida albicans. The thiosemicarbazone proved to be better as antifungal agent than its vanadium complex, probably due to the bulkiness of the complex which does not facilitate its binding to the cell membrane.

Related literature top

For related literature, see: Ahmad et al. (2006); Baran (2000); Beraldo & Gambino (2004); Mendes et al. (2006); Philip et al. (2005); Sreekanth et al. (2003).

Experimental top

Synthesis of 2-benzoylpyridine N(4)-(p-tolyl) thiosemicarbazone has been reported recently (Mendes et al., 2006). The dioxovanadium(V) complex was obtained by mixing equimolar amounts (3 mmol) of the thiosemicarbazone with [VO(acac)₂] (acac= acetylacetonate) in ethanol under reflux and stirring for 24 h. The obtained solid was washed with ethanol and ethyl ether and dried in vacuum·Yield 73%. Single crystals of the complex were growth from 1:9 DMSO/acetone solution.

Structure description top

For related literature, see: Ahmad et al. (2006); Baran (2000); Beraldo & Gambino (2004); Mendes et al. (2006); Philip et al. (2005); Sreekanth et al. (2003).

Computing details top

Data collection: XSCANS (Siemens, 1991); cell refinement: XSCANS; data reduction: XSCANS; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

Figures top

	Fig. 1. The ZE and EZ configurational isomers of H2Bz4pT.
	Fig. 2. Molecular structure of the title compound, showing the atom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability level.

Dioxido{1-[(phenyl)(2-pyridyl)methylene]-4-(p-tolyl)thiosemicarbazonato}vanadium(V) dimethyl sulfoxide solvate top

Crystal data top

[V(C₂₀H₁₇N₄S)O₂]·C₂H₆OS	F(000) = 2096
M_r = 506.5	D_x = 1.418 Mg m⁻³
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 33 reflections
a = 13.9269 (13) Å	θ = 6.4–11.4°
b = 15.399 (2) Å	µ = 0.63 mm⁻¹
c = 22.133 (4) Å	T = 298 K
V = 4746.4 (12) Å³	Prismatic, orange
Z = 8	0.2 × 0.2 × 0.2 mm

Data collection top

Siemens P4 diffractometer	R_int = 0.031
Radiation source: fine-focus sealed tube	θ_max = 25.5°, θ_min = 2.2°
Graphite monochromator	h = −13→16
ω/2θ scans	k = −14→18
6630 measured reflections	l = −21→26
4420 independent reflections	3 standard reflections every 247 reflections
2706 reflections with I > 2σ(I)	intensity decay: 4%

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.059	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.165	H-atom parameters constrained
S = 1.02	w = 1/[σ²(F_o²) + (0.0577P)² + 7.659P] where P = (F_o² + 2F_c²)/3
4420 reflections	(Δ/σ)_max = 0.001
289 parameters	Δρ_max = 0.85 e Å⁻³
0 restraints	Δρ_min = −0.59 e Å⁻³

Crystal data top

[V(C₂₀H₁₇N₄S)O₂]·C₂H₆OS	V = 4746.4 (12) Å³
M_r = 506.5	Z = 8
Orthorhombic, Pbca	Mo Kα radiation
a = 13.9269 (13) Å	µ = 0.63 mm⁻¹
b = 15.399 (2) Å	T = 298 K
c = 22.133 (4) Å	0.2 × 0.2 × 0.2 mm

Data collection top

Siemens P4 diffractometer	R_int = 0.031
6630 measured reflections	3 standard reflections every 247 reflections
4420 independent reflections	intensity decay: 4%
2706 reflections with I > 2σ(I)

Refinement top

R[F² > 2σ(F²)] = 0.059	0 restraints
wR(F²) = 0.165	H-atom parameters constrained
S = 1.02	Δρ_max = 0.85 e Å⁻³
4420 reflections	Δρ_min = −0.59 e Å⁻³
289 parameters

Special details top

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

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
S1	0.34368 (9)	0.09146 (9)	0.65651 (5)	0.0561 (4)
V	0.50439 (6)	0.13499 (6)	0.67446 (3)	0.0491 (3)
O1	0.4814 (3)	0.2109 (3)	0.72207 (18)	0.0966 (16)
O2	0.5450 (3)	0.0505 (3)	0.70781 (19)	0.0936 (14)
N1	0.6366 (3)	0.1836 (2)	0.64408 (16)	0.0479 (9)
C2	0.6489 (3)	0.1988 (3)	0.58420 (19)	0.0435 (10)
C3	0.7355 (3)	0.2282 (3)	0.5620 (2)	0.0529 (12)
H3	0.7429	0.2395	0.5210	0.064*
C4	0.8112 (4)	0.2408 (4)	0.6015 (2)	0.0629 (14)
H4	0.8704	0.2596	0.5871	0.075*
C5	0.7987 (4)	0.2256 (4)	0.6614 (3)	0.0682 (15)
H5	0.8492	0.2336	0.6883	0.082*
C6	0.7108 (4)	0.1982 (4)	0.6816 (2)	0.0640 (15)
H6	0.7021	0.1895	0.7228	0.077*
C7	0.5650 (3)	0.1763 (3)	0.54705 (18)	0.0364 (9)
N2	0.4935 (2)	0.1421 (2)	0.57668 (14)	0.0362 (8)
N3	0.4155 (2)	0.1158 (2)	0.54342 (14)	0.0374 (8)
C8	0.3450 (3)	0.0871 (3)	0.57804 (17)	0.0364 (9)
N4	0.2660 (2)	0.0531 (2)	0.55245 (14)	0.0400 (8)
H4B	0.2220	0.0376	0.5776	0.048*
C9	0.2431 (3)	0.0384 (3)	0.49082 (18)	0.0374 (9)
C10	0.1491 (3)	0.0141 (3)	0.4783 (2)	0.0459 (11)
H10	0.1056	0.0074	0.5099	0.055*
C11	0.1198 (3)	0.0000 (3)	0.4202 (2)	0.0528 (12)
H11	0.0566	−0.0168	0.4131	0.063*
C12	0.1814 (4)	0.0100 (3)	0.3717 (2)	0.0546 (13)
C13	0.2758 (3)	0.0301 (3)	0.3852 (2)	0.0564 (13)
H13	0.3198	0.0341	0.3537	0.068*
C14	0.3074 (3)	0.0445 (3)	0.44336 (19)	0.0475 (11)
H14	0.3714	0.0581	0.4506	0.057*
C15	0.1458 (4)	−0.0011 (5)	0.3077 (2)	0.0866 (19)
H15A	0.0786	−0.0149	0.3082	0.130*
H15B	0.1805	−0.0472	0.2884	0.130*
H15C	0.1556	0.0519	0.2857	0.130*
C16	0.5663 (3)	0.1908 (3)	0.48091 (18)	0.0361 (9)
C17	0.5761 (3)	0.2748 (3)	0.4579 (2)	0.0539 (12)
H17	0.5829	0.3213	0.4844	0.065*
C18	0.5759 (3)	0.2896 (4)	0.3967 (2)	0.0612 (14)
H18	0.5829	0.3458	0.3819	0.073*
C19	0.5654 (3)	0.2216 (4)	0.3572 (2)	0.0605 (14)
H19	0.5647	0.2317	0.3158	0.073*
C20	0.5559 (3)	0.1383 (3)	0.3789 (2)	0.0527 (12)
H20	0.5492	0.0923	0.3520	0.063*
C21	0.5564 (3)	0.1225 (3)	0.44055 (18)	0.0414 (10)
H21	0.5501	0.0660	0.4549	0.050*
S2A	0.90467 (10)	0.09940 (10)	0.35510 (7)	0.0709 (4)
O1A	0.8871 (2)	0.0091 (2)	0.37672 (15)	0.0626 (9)
C1A	0.8368 (5)	0.1666 (4)	0.4021 (3)	0.102 (2)
H1AA	0.8661	0.1692	0.4414	0.152*
H1AB	0.7729	0.1437	0.4058	0.152*
H1AC	0.8340	0.2239	0.3851	0.152*
C2A	0.8358 (7)	0.1097 (5)	0.2909 (3)	0.127 (3)
H2AA	0.8627	0.0747	0.2593	0.191*
H2AB	0.8349	0.1694	0.2784	0.191*
H2AC	0.7715	0.0908	0.2992	0.191*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0483 (7)	0.0871 (10)	0.0330 (6)	−0.0164 (7)	0.0038 (5)	0.0001 (6)
V	0.0433 (4)	0.0734 (6)	0.0307 (4)	−0.0005 (4)	−0.0021 (3)	−0.0039 (4)
O1	0.064 (3)	0.147 (4)	0.079 (3)	−0.018 (3)	0.008 (2)	−0.067 (3)
O2	0.058 (2)	0.139 (4)	0.084 (3)	0.005 (3)	0.002 (2)	0.055 (3)
N1	0.046 (2)	0.059 (2)	0.038 (2)	−0.0004 (19)	−0.0084 (17)	−0.0110 (18)
C2	0.042 (3)	0.045 (3)	0.043 (2)	−0.002 (2)	−0.005 (2)	−0.009 (2)
C3	0.042 (3)	0.063 (3)	0.054 (3)	−0.009 (2)	−0.002 (2)	−0.006 (2)
C4	0.043 (3)	0.073 (4)	0.073 (4)	−0.012 (3)	−0.006 (3)	−0.010 (3)
C5	0.048 (3)	0.087 (4)	0.070 (4)	−0.007 (3)	−0.016 (3)	−0.021 (3)
C6	0.061 (3)	0.088 (4)	0.044 (3)	−0.003 (3)	−0.012 (2)	−0.015 (3)
C7	0.036 (2)	0.032 (2)	0.041 (2)	−0.0014 (18)	−0.0018 (19)	−0.0046 (18)
N2	0.0353 (18)	0.0397 (19)	0.0336 (17)	−0.0065 (16)	−0.0016 (15)	−0.0045 (15)
N3	0.0336 (19)	0.049 (2)	0.0294 (17)	−0.0089 (16)	−0.0014 (15)	−0.0025 (15)
C8	0.040 (2)	0.037 (2)	0.032 (2)	−0.0009 (19)	0.0031 (19)	0.0002 (18)
N4	0.0331 (19)	0.053 (2)	0.0337 (18)	−0.0111 (17)	0.0018 (15)	0.0016 (16)
C9	0.040 (2)	0.033 (2)	0.039 (2)	−0.0012 (19)	−0.0027 (19)	−0.0002 (18)
C10	0.036 (2)	0.054 (3)	0.047 (2)	−0.007 (2)	0.001 (2)	0.000 (2)
C11	0.041 (3)	0.067 (3)	0.051 (3)	−0.006 (2)	−0.014 (2)	−0.009 (2)
C12	0.061 (3)	0.061 (3)	0.042 (3)	0.000 (3)	−0.012 (2)	−0.005 (2)
C13	0.050 (3)	0.078 (4)	0.041 (3)	−0.007 (3)	0.004 (2)	−0.008 (2)
C14	0.035 (2)	0.065 (3)	0.043 (2)	−0.008 (2)	−0.001 (2)	−0.006 (2)
C15	0.082 (4)	0.130 (5)	0.048 (3)	−0.010 (4)	−0.015 (3)	−0.016 (3)
C16	0.028 (2)	0.039 (2)	0.041 (2)	−0.0061 (18)	−0.0005 (17)	0.0006 (19)
C17	0.053 (3)	0.045 (3)	0.063 (3)	−0.011 (2)	0.000 (2)	0.003 (2)
C18	0.052 (3)	0.060 (3)	0.072 (4)	−0.007 (3)	−0.002 (3)	0.028 (3)
C19	0.048 (3)	0.092 (4)	0.041 (3)	−0.006 (3)	0.000 (2)	0.020 (3)
C20	0.049 (3)	0.070 (3)	0.039 (2)	−0.005 (3)	0.001 (2)	−0.007 (2)
C21	0.040 (2)	0.045 (3)	0.040 (2)	−0.005 (2)	0.0011 (19)	0.001 (2)
S2A	0.0606 (9)	0.0785 (10)	0.0736 (9)	−0.0067 (8)	0.0075 (7)	0.0188 (8)
O1A	0.054 (2)	0.062 (2)	0.072 (2)	−0.0053 (17)	0.0155 (17)	0.0183 (18)
C1A	0.125 (6)	0.063 (4)	0.116 (6)	−0.003 (4)	0.021 (5)	−0.018 (4)
C2A	0.175 (9)	0.114 (6)	0.093 (5)	−0.011 (6)	−0.041 (6)	0.014 (5)

Geometric parameters (Å, º) top

S1—C8	1.738 (4)	C11—H11	0.9300
S1—V	2.3699 (14)	C12—C13	1.383 (7)
V—O2	1.599 (4)	C12—C15	1.512 (6)
V—O1	1.606 (4)	C13—C14	1.379 (6)
V—N1	2.099 (4)	C13—H13	0.9300
V—N2	2.172 (3)	C14—H14	0.9300
N1—C6	1.344 (6)	C15—H15A	0.9600
N1—C2	1.357 (5)	C15—H15B	0.9600
C2—C3	1.379 (6)	C15—H15C	0.9600
C2—C7	1.469 (6)	C16—C21	1.387 (6)
C3—C4	1.384 (6)	C16—C17	1.397 (6)
C3—H3	0.9300	C17—C18	1.375 (7)
C4—C5	1.357 (7)	C17—H17	0.9300
C4—H4	0.9300	C18—C19	1.372 (7)
C5—C6	1.370 (7)	C18—H18	0.9300
C5—H5	0.9300	C19—C20	1.375 (7)
C6—H6	0.9300	C19—H19	0.9300
C7—N2	1.304 (5)	C20—C21	1.386 (6)
C7—C16	1.481 (6)	C20—H20	0.9300
N2—N3	1.374 (4)	C21—H21	0.9300
N3—C8	1.322 (5)	S2A—O1A	1.491 (4)
C8—N4	1.344 (5)	S2A—C2A	1.722 (7)
N4—C9	1.418 (5)	S2A—C1A	1.746 (6)
N4—H4B	0.8600	C1A—H1AA	0.9600
C9—C14	1.383 (6)	C1A—H1AB	0.9600
C9—C10	1.390 (6)	C1A—H1AC	0.9600
C10—C11	1.367 (6)	C2A—H2AA	0.9600
C10—H10	0.9300	C2A—H2AB	0.9600
C11—C12	1.384 (7)	C2A—H2AC	0.9600

C8—S1—V	99.71 (15)	C12—C11—H11	119.1
O2—V—O1	111.1 (3)	C13—C12—C11	116.6 (4)
O2—V—N1	97.32 (18)	C13—C12—C15	122.7 (5)
O1—V—N1	97.21 (18)	C11—C12—C15	120.8 (5)
O2—V—N2	121.7 (2)	C14—C13—C12	122.7 (4)
O1—V—N2	127.1 (2)	C14—C13—H13	118.6
N1—V—N2	73.97 (13)	C12—C13—H13	118.6
O2—V—S1	100.46 (16)	C13—C14—C9	119.5 (4)
O1—V—S1	97.33 (14)	C13—C14—H14	120.3
N1—V—S1	151.15 (10)	C9—C14—H14	120.3
N2—V—S1	77.38 (9)	C12—C15—H15A	109.5
C6—N1—C2	118.5 (4)	C12—C15—H15B	109.5
C6—N1—V	122.4 (3)	H15A—C15—H15B	109.5
C2—N1—V	119.0 (3)	C12—C15—H15C	109.5
N1—C2—C3	121.0 (4)	H15A—C15—H15C	109.5
N1—C2—C7	114.0 (4)	H15B—C15—H15C	109.5
C3—C2—C7	125.0 (4)	C21—C16—C17	118.5 (4)
C2—C3—C4	119.2 (5)	C21—C16—C7	121.4 (4)
C2—C3—H3	120.4	C17—C16—C7	120.1 (4)
C4—C3—H3	120.4	C18—C17—C16	120.8 (5)
C5—C4—C3	119.6 (5)	C18—C17—H17	119.6
C5—C4—H4	120.2	C16—C17—H17	119.6
C3—C4—H4	120.2	C19—C18—C17	120.1 (5)
C4—C5—C6	119.1 (5)	C19—C18—H18	120.0
C4—C5—H5	120.4	C17—C18—H18	120.0
C6—C5—H5	120.4	C18—C19—C20	120.0 (4)
N1—C6—C5	122.5 (5)	C18—C19—H19	120.0
N1—C6—H6	118.8	C20—C19—H19	120.0
C5—C6—H6	118.8	C19—C20—C21	120.5 (5)
N2—C7—C2	114.9 (4)	C19—C20—H20	119.8
N2—C7—C16	124.5 (3)	C21—C20—H20	119.8
C2—C7—C16	120.6 (4)	C20—C21—C16	120.0 (4)
C7—N2—N3	117.0 (3)	C20—C21—H21	120.0
C7—N2—V	117.9 (3)	C16—C21—H21	120.0
N3—N2—V	125.0 (2)	O1A—S2A—C2A	105.0 (3)
C8—N3—N2	112.1 (3)	O1A—S2A—C1A	105.8 (3)
N3—C8—N4	119.6 (3)	C2A—S2A—C1A	97.8 (4)
N3—C8—S1	125.0 (3)	S2A—C1A—H1AA	109.5
N4—C8—S1	115.3 (3)	S2A—C1A—H1AB	109.5
C8—N4—C9	130.6 (3)	H1AA—C1A—H1AB	109.5
C8—N4—H4B	114.7	S2A—C1A—H1AC	109.5
C9—N4—H4B	114.7	H1AA—C1A—H1AC	109.5
C14—C9—C10	118.5 (4)	H1AB—C1A—H1AC	109.5
C14—C9—N4	125.1 (4)	S2A—C2A—H2AA	109.5
C10—C9—N4	116.4 (4)	S2A—C2A—H2AB	109.5
C11—C10—C9	120.7 (4)	H2AA—C2A—H2AB	109.5
C11—C10—H10	119.6	S2A—C2A—H2AC	109.5
C9—C10—H10	119.6	H2AA—C2A—H2AC	109.5
C10—C11—C12	121.8 (4)	H2AB—C2A—H2AC	109.5
C10—C11—H11	119.1

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N4—H4B···O1Aⁱ	0.86	1.96	2.814 (4)	170

Symmetry code: (i) −x+1, −y, −z+1.

Experimental details

Crystal data
Chemical formula	[V(C₂₀H₁₇N₄S)O₂]·C₂H₆OS
M_r	506.5
Crystal system, space group	Orthorhombic, Pbca
Temperature (K)	298
a, b, c (Å)	13.9269 (13), 15.399 (2), 22.133 (4)
V (Å³)	4746.4 (12)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.63
Crystal size (mm)	0.2 × 0.2 × 0.2

Data collection
Diffractometer	Siemens P4
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	6630, 4420, 2706
R_int	0.031
(sin θ/λ)_max (Å⁻¹)	0.606

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.059, 0.165, 1.02
No. of reflections	4420
No. of parameters	289
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.85, −0.59

Computer programs: XSCANS (Siemens, 1991), XSCANS, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), ORTEP-3 (Farrugia, 1997), WinGX (Farrugia, 1999).

Selected geometric parameters (Å, º) top

S1—C8	1.738 (4)	V—N1	2.099 (4)
S1—V	2.3699 (14)	V—N2	2.172 (3)
V—O2	1.599 (4)	N3—C8	1.322 (5)
V—O1	1.606 (4)

O2—V—O1	111.1 (3)	N1—V—S1	151.15 (10)
O2—V—N2	121.7 (2)	C8—N3—N2	112.1 (3)
O1—V—N2	127.1 (2)	N3—C8—S1	125.0 (3)