Di-μ-dioxo-bis­({1-[phen­yl(2-pyridyl-κN)methyl­ene]-2-(pyrrolidin-1-ylthio­carbonyl-κS)hydrazinato-κN¹}oxovanadium(V))

In the title centrosymmetric binuclear complex, [V₂(C₁₇H₁₇N₄S)₂O₄], pairs of V atoms are linked by two oxo bridges. The coordination geometry at each V^V atom is distorted octa­hedral, involving a pyridine N atom, a thiol­ate S atom, an azomethine N atom from the 1-[phen­yl(2-pyrid­yl)methyl­ene]-2-(pyrrolidin-1-ylthio­carbon­yl)hydrazine(−) ligand, and one terminal O and 2 bridging O atoms. The crystal structure is stabilized by weak inter­molecular C—H...O inter­actions.

Key indicators

• Single-crystal X-ray study
• T = 297 K
• Mean [sigma](C-C) = 0.005 Å
• R factor = 0.051
• wR factor = 0.120
• Data-to-parameter ratio = 15.6

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical .          ?
PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X)  V1     -   S1      ..       6.16 su
PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X)  V1     -   O1      ..       5.72 su

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

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

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Computing details

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 1998); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2003).

Di-µ-dioxo-bis({1-[phenyl(2-pyridyl-κN)methylene]-2-(pyrrolidin-1- ylthiocarbonyl-κS)hydrazinato-κN¹}oxovanadium(V))

Crystal data

[V2(C17H17N4S)2O4]	F(000) = 808
Mr = 784.71	Dx = 1.483 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3801 reflections
a = 10.3912 (8) Å	θ = 2.4–27.0°
b = 17.4103 (14) Å	µ = 0.70 mm^−1
c = 11.0953 (7) Å	T = 297 K
β = 118.877 (5)°	Slab, light brown
V = 1757.7 (2) Å^3	0.52 × 0.44 × 0.18 mm
Z = 2

Data collection

Bruker SMART APEX2 CCD area-detector diffractometer	3801 independent reflections
Radiation source: fine-focus sealed tube	3129 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.026
Detector resolution: 8.33 pixels mm^-1	θmax = 27.0°, θmin = 2.4°
ω scans	h = −11→13
Absorption correction: multi-scan (SADABS; Bruker, 2005)	k = −22→14
Tmin = 0.701, Tmax = 0.881	l = −13→14
9824 measured reflections

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.051	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.120	H-atom parameters constrained
S = 1.16	w = 1/[σ^2(Fo^2) + (0.0428P)^2 + 1.5976P] where P = (Fo^2 + 2Fc^2)/3
3801 reflections	(Δ/σ)max < 0.001
243 parameters	Δρmax = 0.41 e Å^−3
0 restraints	Δρmin = −0.30 e Å^−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
V1	0.06919 (5)	−0.04935 (3)	0.42557 (5)	0.02977 (15)
S1	−0.04038 (9)	0.02495 (5)	0.21876 (8)	0.0462 (2)
O1	−0.1336 (2)	−0.02113 (11)	0.4579 (2)	0.0377 (5)
O2	0.2073 (2)	−0.07935 (13)	0.4101 (2)	0.0480 (6)
N1	−0.2805 (3)	−0.01175 (15)	−0.0109 (2)	0.0447 (6)
N2	−0.2090 (3)	−0.10543 (13)	0.1505 (2)	0.0343 (5)
N3	−0.1085 (2)	−0.12367 (13)	0.2826 (2)	0.0294 (5)
N4	0.0790 (2)	−0.14950 (13)	0.5379 (2)	0.0340 (5)
C1	−0.4095 (4)	−0.0570 (2)	−0.1060 (3)	0.0558 (9)
H1A	−0.4651	−0.0742	−0.0615	0.056 (11)*
H1B	−0.3809	−0.1014	−0.1406	0.093 (16)*
C2	−0.4977 (4)	0.0000 (3)	−0.2207 (4)	0.0635 (11)
H2A	−0.5524	−0.0261	−0.3083	0.071 (12)*
H2B	−0.5656	0.0287	−0.2014	0.093 (16)*
C3	−0.3832 (4)	0.0517 (3)	−0.2218 (4)	0.0657 (11)
H3A	−0.4253	0.1011	−0.2615	0.083 (14)*
H3B	−0.3411	0.0290	−0.2747	0.082 (14)*
C4	−0.2670 (5)	0.0605 (2)	−0.0716 (4)	0.0620 (11)
H4A	−0.1697	0.0661	−0.0621	0.086 (15)*
H4B	−0.2876	0.1043	−0.0296	0.071 (13)*
C5	−0.1847 (3)	−0.03602 (16)	0.1153 (3)	0.0349 (6)
C6	−0.1226 (3)	−0.19123 (15)	0.3264 (3)	0.0315 (6)
C7	−0.2403 (3)	−0.24637 (16)	0.2389 (3)	0.0336 (6)
C8	−0.2090 (4)	−0.30983 (18)	0.1816 (4)	0.0466 (8)
H8A	−0.1126	−0.3197	0.2022	0.046 (9)*
C9	−0.3207 (4)	−0.3586 (2)	0.0941 (4)	0.0583 (9)
H9A	−0.2994	−0.4004	0.0546	0.055 (10)*
C10	−0.4628 (4)	−0.3451 (2)	0.0656 (4)	0.0597 (10)
H10A	−0.5376	−0.3780	0.0074	0.078 (13)*
C11	−0.4945 (4)	−0.2834 (3)	0.1227 (4)	0.0618 (10)
H11A	−0.5908	−0.2745	0.1034	0.078 (13)*
C12	−0.3836 (4)	−0.2338 (2)	0.2094 (4)	0.0543 (9)
H12A	−0.4061	−0.1919	0.2478	0.077 (13)*
C13	−0.0148 (3)	−0.20804 (16)	0.4685 (3)	0.0333 (6)
C14	−0.0037 (4)	−0.27847 (18)	0.5322 (3)	0.0444 (7)
H14A	−0.0693	−0.3179	0.4850	0.047 (9)*
C15	0.1057 (4)	−0.2892 (2)	0.6664 (4)	0.0504 (8)
H15A	0.1154	−0.3361	0.7099	0.051 (10)*
C16	0.1999 (4)	−0.2301 (2)	0.7348 (3)	0.0525 (9)
H16A	0.2739	−0.2365	0.8251	0.056 (10)*
C17	0.1837 (3)	−0.16067 (19)	0.6683 (3)	0.0433 (7)
H17A	0.2475	−0.1206	0.7154	0.045 (9)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
V1	0.0286 (2)	0.0281 (2)	0.0260 (2)	−0.00133 (19)	0.00795 (18)	−0.00291 (19)
S1	0.0530 (5)	0.0371 (4)	0.0327 (4)	−0.0145 (4)	0.0081 (3)	0.0020 (3)
O1	0.0345 (10)	0.0359 (11)	0.0361 (11)	−0.0045 (9)	0.0117 (9)	−0.0090 (9)
O2	0.0427 (12)	0.0506 (13)	0.0501 (13)	0.0022 (10)	0.0219 (10)	−0.0062 (11)
N1	0.0474 (15)	0.0409 (15)	0.0295 (13)	−0.0078 (12)	0.0056 (11)	0.0080 (11)
N2	0.0376 (13)	0.0293 (12)	0.0253 (11)	−0.0032 (10)	0.0066 (10)	0.0010 (9)
N3	0.0320 (11)	0.0266 (11)	0.0233 (11)	0.0009 (9)	0.0085 (9)	−0.0024 (9)
N4	0.0332 (12)	0.0327 (12)	0.0298 (12)	0.0055 (10)	0.0102 (10)	0.0041 (10)
C1	0.0492 (19)	0.061 (2)	0.0341 (16)	−0.0098 (17)	0.0020 (15)	0.0054 (16)
C2	0.052 (2)	0.081 (3)	0.0375 (19)	0.007 (2)	0.0056 (16)	0.0086 (19)
C3	0.066 (2)	0.078 (3)	0.044 (2)	0.013 (2)	0.0186 (18)	0.027 (2)
C4	0.073 (3)	0.052 (2)	0.045 (2)	−0.0049 (19)	0.0162 (18)	0.0213 (17)
C5	0.0379 (15)	0.0327 (15)	0.0278 (13)	−0.0018 (12)	0.0107 (12)	0.0002 (11)
C6	0.0338 (14)	0.0272 (14)	0.0315 (14)	0.0006 (11)	0.0143 (11)	−0.0010 (11)
C7	0.0335 (14)	0.0282 (14)	0.0338 (14)	−0.0033 (11)	0.0120 (12)	0.0034 (11)
C8	0.0411 (17)	0.0377 (17)	0.060 (2)	−0.0045 (14)	0.0231 (15)	−0.0081 (15)
C9	0.065 (2)	0.048 (2)	0.062 (2)	−0.0170 (18)	0.0311 (19)	−0.0188 (18)
C10	0.055 (2)	0.067 (2)	0.0418 (19)	−0.0282 (19)	0.0113 (16)	−0.0033 (18)
C11	0.0334 (18)	0.077 (3)	0.064 (2)	−0.0106 (18)	0.0147 (16)	0.004 (2)
C12	0.0452 (19)	0.051 (2)	0.068 (2)	0.0006 (16)	0.0279 (17)	−0.0034 (18)
C13	0.0345 (14)	0.0313 (14)	0.0341 (14)	0.0043 (12)	0.0165 (12)	0.0013 (12)
C14	0.0520 (18)	0.0352 (16)	0.0464 (18)	0.0026 (14)	0.0240 (15)	0.0102 (14)
C15	0.062 (2)	0.0462 (19)	0.0496 (19)	0.0203 (17)	0.0323 (17)	0.0236 (16)
C16	0.0511 (19)	0.065 (2)	0.0314 (16)	0.0194 (17)	0.0122 (14)	0.0136 (16)
C17	0.0380 (16)	0.0489 (19)	0.0320 (15)	0.0071 (14)	0.0081 (13)	0.0028 (14)

Geometric parameters (Å, º)

V1—O2	1.612 (2)	C3—H3B	0.9701
V1—O1^i	1.6702 (19)	C4—H4A	0.9699
V1—N4	2.117 (2)	C4—H4B	0.9701
V1—N3	2.184 (2)	C6—C13	1.456 (4)
V1—O1	2.354 (2)	C6—C7	1.488 (4)
V1—S1	2.3899 (9)	C7—C12	1.378 (4)
S1—C5	1.741 (3)	C7—C8	1.389 (4)
O1—V1^i	1.6702 (19)	C8—C9	1.386 (5)
N1—C5	1.336 (4)	C8—H8A	0.9300
N1—C4	1.465 (4)	C9—C10	1.372 (5)
N1—C1	1.471 (4)	C9—H9A	0.9301
N2—C5	1.331 (4)	C10—C11	1.366 (6)
N2—N3	1.364 (3)	C10—H10A	0.9301
N3—C6	1.308 (3)	C11—C12	1.389 (5)
N4—C17	1.339 (4)	C11—H11A	0.9300
N4—C13	1.363 (4)	C12—H12A	0.9300
C1—C2	1.523 (5)	C13—C14	1.392 (4)
C1—H1A	0.9700	C14—C15	1.381 (5)
C1—H1B	0.9701	C14—H14A	0.9299
C2—C3	1.495 (6)	C15—C16	1.369 (5)
C2—H2A	0.9700	C15—H15A	0.9301
C2—H2B	0.9700	C16—C17	1.383 (5)
C3—C4	1.522 (5)	C16—H16A	0.9300
C3—H3A	0.9699	C17—H17A	0.9299
O2—V1—O1^i	106.01 (11)	N1—C4—C3	102.4 (3)
O2—V1—N4	90.21 (11)	N1—C4—H4A	111.3
O1^i—V1—N4	105.18 (10)	C3—C4—H4A	111.3
O2—V1—N3	102.39 (10)	N1—C4—H4B	111.3
O1^i—V1—N3	151.59 (9)	C3—C4—H4B	111.3
N4—V1—N3	73.93 (9)	H4A—C4—H4B	109.2
O2—V1—O1	172.83 (10)	N2—C5—N1	116.3 (2)
O1^i—V1—O1	77.42 (9)	N2—C5—S1	125.8 (2)
N4—V1—O1	82.77 (8)	N1—C5—S1	117.8 (2)
N3—V1—O1	74.30 (7)	N3—C6—C13	114.7 (2)
O2—V1—S1	96.26 (9)	N3—C6—C7	122.8 (2)
O1^i—V1—S1	99.93 (8)	C13—C6—C7	122.5 (2)
N4—V1—S1	151.20 (7)	C12—C7—C8	118.8 (3)
N3—V1—S1	77.27 (6)	C12—C7—C6	120.4 (3)
O1—V1—S1	89.25 (6)	C8—C7—C6	120.8 (3)
C5—S1—V1	99.34 (10)	C9—C8—C7	120.4 (3)
V1^i—O1—V1	102.59 (9)	C9—C8—H8A	119.8
C5—N1—C4	124.4 (3)	C7—C8—H8A	119.8
C5—N1—C1	122.8 (3)	C10—C9—C8	120.0 (4)
C4—N1—C1	112.8 (3)	C10—C9—H9A	120.0
C5—N2—N3	111.8 (2)	C8—C9—H9A	120.0
C6—N3—N2	116.3 (2)	C11—C10—C9	120.1 (3)
C6—N3—V1	118.03 (17)	C11—C10—H10A	119.9
N2—N3—V1	125.62 (17)	C9—C10—H10A	120.0
C17—N4—C13	119.2 (3)	C10—C11—C12	120.3 (3)
C17—N4—V1	122.6 (2)	C10—C11—H11A	119.8
C13—N4—V1	117.71 (18)	C12—C11—H11A	119.8
N1—C1—C2	102.8 (3)	C7—C12—C11	120.4 (4)
N1—C1—H1A	111.1	C7—C12—H12A	119.8
C2—C1—H1A	111.1	C11—C12—H12A	119.8
N1—C1—H1B	111.3	N4—C13—C14	120.7 (3)
C2—C1—H1B	111.3	N4—C13—C6	115.4 (2)
H1A—C1—H1B	109.1	C14—C13—C6	124.0 (3)
C3—C2—C1	103.8 (3)	C15—C14—C13	119.3 (3)
C3—C2—H2A	111.0	C15—C14—H14A	120.4
C1—C2—H2A	110.9	C13—C14—H14A	120.4
C3—C2—H2B	111.0	C16—C15—C14	119.5 (3)
C1—C2—H2B	111.1	C16—C15—H15A	120.3
H2A—C2—H2B	109.0	C14—C15—H15A	120.3
C2—C3—C4	105.4 (3)	C15—C16—C17	119.4 (3)
C2—C3—H3A	110.6	C15—C16—H16A	120.3
C4—C3—H3A	110.7	C17—C16—H16A	120.3
C2—C3—H3B	110.7	N4—C17—C16	121.9 (3)
C4—C3—H3B	110.6	N4—C17—H17A	119.0
H3A—C3—H3B	108.8	C16—C17—H17A	119.0
O2—V1—S1—C5	104.30 (14)	N3—N2—C5—S1	2.2 (4)
O1^i—V1—S1—C5	−148.18 (13)	C4—N1—C5—N2	−175.8 (3)
N4—V1—S1—C5	2.33 (19)	C1—N1—C5—N2	2.0 (5)
N3—V1—S1—C5	2.97 (12)	C4—N1—C5—S1	4.2 (5)
O1—V1—S1—C5	−71.10 (12)	C1—N1—C5—S1	−178.0 (3)
O1^i—V1—O1—V1^i	0.0	V1—S1—C5—N2	−4.1 (3)
N4—V1—O1—V1^i	107.39 (11)	V1—S1—C5—N1	175.9 (2)
N3—V1—O1—V1^i	−177.33 (12)	N2—N3—C6—C13	−179.1 (2)
S1—V1—O1—V1^i	−100.35 (9)	V1—N3—C6—C13	−0.1 (3)
C5—N2—N3—C6	−179.5 (2)	N2—N3—C6—C7	0.3 (4)
C5—N2—N3—V1	1.6 (3)	V1—N3—C6—C7	179.3 (2)
O2—V1—N3—C6	84.2 (2)	N3—C6—C7—C12	−73.8 (4)
O1^i—V1—N3—C6	−94.7 (3)	C13—C6—C7—C12	105.6 (3)
N4—V1—N3—C6	−2.4 (2)	N3—C6—C7—C8	104.0 (3)
O1—V1—N3—C6	−89.2 (2)	C13—C6—C7—C8	−76.6 (4)
S1—V1—N3—C6	177.9 (2)	C12—C7—C8—C9	1.4 (5)
O2—V1—N3—N2	−96.9 (2)	C6—C7—C8—C9	−176.4 (3)
O1^i—V1—N3—N2	84.2 (3)	C7—C8—C9—C10	−1.2 (5)
N4—V1—N3—N2	176.5 (2)	C8—C9—C10—C11	0.4 (6)
O1—V1—N3—N2	89.7 (2)	C9—C10—C11—C12	0.2 (6)
S1—V1—N3—N2	−3.15 (19)	C8—C7—C12—C11	−0.7 (5)
O2—V1—N4—C17	73.8 (2)	C6—C7—C12—C11	177.1 (3)
O1^i—V1—N4—C17	−32.9 (2)	C10—C11—C12—C7	−0.1 (6)
N3—V1—N4—C17	176.6 (2)	C17—N4—C13—C14	0.9 (4)
O1—V1—N4—C17	−107.7 (2)	V1—N4—C13—C14	173.1 (2)
S1—V1—N4—C17	177.28 (18)	C17—N4—C13—C6	−178.6 (3)
O2—V1—N4—C13	−98.2 (2)	V1—N4—C13—C6	−6.3 (3)
O1^i—V1—N4—C13	155.1 (2)	N3—C6—C13—N4	4.1 (4)
N3—V1—N4—C13	4.65 (19)	C7—C6—C13—N4	−175.3 (3)
O1—V1—N4—C13	80.3 (2)	N3—C6—C13—C14	−175.3 (3)
S1—V1—N4—C13	5.3 (3)	C7—C6—C13—C14	5.3 (4)
C5—N1—C1—C2	169.3 (3)	N4—C13—C14—C15	−1.4 (5)
C4—N1—C1—C2	−12.7 (4)	C6—C13—C14—C15	178.0 (3)
N1—C1—C2—C3	29.8 (4)	C13—C14—C15—C16	0.9 (5)
C1—C2—C3—C4	−36.6 (5)	C14—C15—C16—C17	0.0 (5)
C5—N1—C4—C3	168.7 (3)	C13—N4—C17—C16	0.1 (4)
C1—N1—C4—C3	−9.3 (5)	V1—N4—C17—C16	−171.8 (2)
C2—C3—C4—N1	28.2 (5)	C15—C16—C17—N4	−0.5 (5)
N3—N2—C5—N1	−177.8 (2)

Symmetry code: (i) −x, −y, −z+1.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C10—H10A···O2^ii	0.93	2.45	3.278 (5)	149
C15—H15A···O2^iii	0.93	2.44	3.302 (4)	154

Symmetry codes: (ii) x−1, −y−1/2, z−1/2; (iii) x, −y−1/2, z+1/2.