{2-[2-(N,N′-Di­methyl­amino)­ethyl­imino­methyl]­phenolato-κ³N,N′,O}dioxovanadium(V)

Oxovanadium(V) complexes of N,N′-di­methyl­ethyl­enedi­amine­(salicyl­aldehyde) have been prepared and characterized. The structure of the title compound, [VO₂(C₁₁H₁₅N₂O)], reveals that the vanadium(V) centre is five-coordinate, with a distorted square-pyramidal environment.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.034
• wR factor = 0.098
• Data-to-parameter ratio = 13.7

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT230_ALERT_2_C Hirshfeld Test Diff for    N2     -   C9      ..       5.53 su
PLAT242_ALERT_2_C Check Low    U(eq) as Compared to Neighbors  for         N2

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

   0 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: SMART (Bruker, 1997); cell refinement: SMART; data reduction: SAINT (Bruker, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPIII (Burnett & Johnson, 1996) and ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: SHELXTL (Bruker, 1998).

{2-[2-(N,N'-dimethylamino)ethyliminomethyl]phenolato- κ³N,N',O}dioxovanadium(V)

Crystal data

[V(C11H15N2O)O2]	F(000) = 568
Mr = 274.19	Dx = 1.506 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 946 reflections
a = 6.3250 (19) Å	θ = 3.1–25.9°
b = 15.945 (5) Å	µ = 0.82 mm^−1
c = 11.995 (4) Å	T = 293 K
β = 90.645 (5)°	Block, yellow
V = 1209.6 (7) Å^3	0.22 × 0.20 × 0.16 mm
Z = 4

Data collection

Bruker SMART CCD area-detector diffractometer	2140 independent reflections
Radiation source: fine-focus sealed tube	1736 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.026
φ and ω scans	θmax = 25.0°, θmin = 2.1°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −7→7
Tmin = 0.813, Tmax = 0.877	k = −18→18
6160 measured reflections	l = −6→14

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)] = 0.034	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.098	H-atom parameters constrained
S = 1.05	w = 1/[σ^2(Fo^2) + (0.0574P)^2 + 0.3272P] where P = (Fo^2 + 2Fc^2)/3
2140 reflections	(Δ/σ)max < 0.001
156 parameters	Δρmax = 0.34 e Å^−3
0 restraints	Δρmin = −0.27 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	0.16728 (6)	0.27608 (2)	0.93052 (3)	0.03190 (16)
O1	0.2004 (3)	0.38594 (11)	0.86777 (15)	0.0430 (4)
O2	0.0730 (3)	0.21886 (12)	0.83121 (15)	0.0514 (5)
O3	0.4157 (3)	0.25441 (13)	0.94976 (19)	0.0582 (6)
N1	−0.0940 (3)	0.33215 (12)	1.01403 (16)	0.0349 (5)
N2	0.0906 (3)	0.18662 (13)	1.06231 (17)	0.0394 (5)
C1	0.0573 (4)	0.44218 (14)	0.8363 (2)	0.0354 (5)
C2	0.1074 (5)	0.50035 (16)	0.7533 (2)	0.0465 (7)
H2	0.2413	0.4996	0.7220	0.056*
C3	−0.0392 (5)	0.55874 (17)	0.7173 (2)	0.0546 (8)
H3	−0.0034	0.5965	0.6616	0.066*
C4	−0.2385 (5)	0.56180 (17)	0.7631 (3)	0.0555 (8)
H4	−0.3373	0.6007	0.7377	0.067*
C5	−0.2882 (4)	0.50714 (17)	0.8457 (2)	0.0491 (7)
H5	−0.4214	0.5099	0.8776	0.059*
C6	−0.1430 (4)	0.44651 (15)	0.8843 (2)	0.0355 (5)
C7	−0.2031 (4)	0.39271 (16)	0.9745 (2)	0.0408 (6)
H7	−0.3333	0.4030	1.0070	0.049*
C8	−0.1846 (5)	0.28560 (17)	1.1081 (2)	0.0472 (7)
H8A	−0.3360	0.2946	1.1113	0.057*
H8B	−0.1212	0.3040	1.1779	0.057*
C9	−0.1371 (4)	0.19461 (19)	1.0880 (2)	0.0522 (7)
H9A	−0.1703	0.1620	1.1537	0.063*
H9B	−0.2220	0.1738	1.0261	0.063*
C10	0.2198 (6)	0.2055 (2)	1.1643 (3)	0.0653 (9)
H10A	0.1600	0.1774	1.2273	0.098*
H10B	0.2205	0.2649	1.1773	0.098*
H10C	0.3621	0.1863	1.1537	0.098*
C11	0.1366 (6)	0.10000 (18)	1.0275 (3)	0.0749 (10)
H11A	0.2823	0.0957	1.0067	0.112*
H11B	0.0481	0.0855	0.9649	0.112*
H11C	0.1093	0.0624	1.0881	0.112*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
V1	0.0315 (2)	0.0356 (3)	0.0287 (2)	0.00011 (17)	0.00297 (16)	0.00341 (17)
O1	0.0372 (9)	0.0406 (10)	0.0514 (11)	0.0025 (8)	0.0123 (8)	0.0136 (8)
O2	0.0668 (13)	0.0557 (11)	0.0317 (10)	−0.0076 (9)	0.0050 (9)	−0.0059 (8)
O3	0.0360 (10)	0.0665 (13)	0.0721 (14)	0.0036 (9)	0.0004 (10)	0.0242 (11)
N1	0.0360 (11)	0.0383 (11)	0.0305 (10)	−0.0063 (9)	0.0056 (8)	−0.0022 (9)
N2	0.0483 (13)	0.0352 (11)	0.0346 (11)	−0.0053 (9)	−0.0012 (9)	0.0053 (9)
C1	0.0418 (14)	0.0291 (12)	0.0354 (13)	−0.0037 (10)	0.0000 (11)	−0.0011 (10)
C2	0.0566 (17)	0.0395 (15)	0.0433 (15)	−0.0023 (12)	0.0055 (13)	0.0052 (12)
C3	0.086 (2)	0.0350 (15)	0.0424 (15)	−0.0024 (14)	−0.0077 (15)	0.0051 (12)
C4	0.072 (2)	0.0386 (15)	0.0557 (18)	0.0138 (14)	−0.0184 (16)	−0.0030 (13)
C5	0.0483 (16)	0.0443 (15)	0.0546 (17)	0.0105 (13)	−0.0048 (13)	−0.0107 (14)
C6	0.0400 (13)	0.0310 (12)	0.0355 (13)	0.0014 (10)	−0.0010 (11)	−0.0066 (10)
C7	0.0374 (13)	0.0433 (14)	0.0420 (14)	−0.0008 (12)	0.0076 (11)	−0.0108 (12)
C8	0.0469 (15)	0.0573 (17)	0.0376 (14)	−0.0062 (13)	0.0162 (12)	0.0044 (13)
C9	0.0574 (18)	0.0574 (17)	0.0419 (15)	−0.0220 (14)	0.0013 (13)	0.0100 (13)
C10	0.070 (2)	0.080 (2)	0.0453 (17)	−0.0092 (17)	−0.0179 (15)	0.0174 (16)
C11	0.115 (3)	0.0388 (17)	0.072 (2)	−0.0005 (18)	0.017 (2)	0.0100 (16)

Geometric parameters (Å, º)

V1—O2	1.6097 (19)	C4—C5	1.360 (4)
V1—O3	1.622 (2)	C4—H4	0.9300
V1—O1	1.9190 (18)	C5—C6	1.408 (4)
V1—N1	2.138 (2)	C5—H5	0.9300
V1—N2	2.188 (2)	C6—C7	1.435 (4)
O1—C1	1.326 (3)	C7—H7	0.9300
N1—C7	1.275 (3)	C8—C9	1.502 (4)
N1—C8	1.472 (3)	C8—H8A	0.9700
N2—C11	1.473 (4)	C8—H8B	0.9700
N2—C9	1.482 (3)	C9—H9A	0.9700
N2—C10	1.494 (4)	C9—H9B	0.9700
C1—C6	1.399 (3)	C10—H10A	0.9600
C1—C2	1.400 (3)	C10—H10B	0.9600
C2—C3	1.380 (4)	C10—H10C	0.9600
C2—H2	0.9300	C11—H11A	0.9600
C3—C4	1.381 (4)	C11—H11B	0.9600
C3—H3	0.9300	C11—H11C	0.9600
O2—V1—O3	109.54 (11)	C4—C5—H5	119.2
O2—V1—O1	105.57 (9)	C6—C5—H5	119.2
O3—V1—O1	98.07 (9)	C1—C6—C5	119.3 (2)
O2—V1—N1	107.57 (9)	C1—C6—C7	121.9 (2)
O3—V1—N1	140.78 (10)	C5—C6—C7	118.7 (2)
O1—V1—N1	83.72 (7)	N1—C7—C6	125.9 (2)
O2—V1—N2	94.70 (9)	N1—C7—H7	117.0
O3—V1—N2	88.87 (9)	C6—C7—H7	117.0
O1—V1—N2	154.78 (8)	N1—C8—C9	106.5 (2)
N1—V1—N2	75.84 (8)	N1—C8—H8A	110.4
C1—O1—V1	130.66 (15)	C9—C8—H8A	110.4
C7—N1—C8	117.0 (2)	N1—C8—H8B	110.4
C7—N1—V1	124.06 (17)	C9—C8—H8B	110.4
C8—N1—V1	117.25 (17)	H8A—C8—H8B	108.6
C11—N2—C9	109.6 (2)	N2—C9—C8	108.3 (2)
C11—N2—C10	108.3 (3)	N2—C9—H9A	110.0
C9—N2—C10	109.7 (2)	C8—C9—H9A	110.0
C11—N2—V1	111.12 (17)	N2—C9—H9B	110.0
C9—N2—V1	108.54 (16)	C8—C9—H9B	110.0
C10—N2—V1	109.66 (17)	H9A—C9—H9B	108.4
O1—C1—C6	122.3 (2)	N2—C10—H10A	109.5
O1—C1—C2	119.4 (2)	N2—C10—H10B	109.5
C6—C1—C2	118.3 (2)	H10A—C10—H10B	109.5
C3—C2—C1	120.8 (3)	N2—C10—H10C	109.5
C3—C2—H2	119.6	H10A—C10—H10C	109.5
C1—C2—H2	119.6	H10B—C10—H10C	109.5
C2—C3—C4	120.8 (3)	N2—C11—H11A	109.5
C2—C3—H3	119.6	N2—C11—H11B	109.5
C4—C3—H3	119.6	H11A—C11—H11B	109.5
C5—C4—C3	119.1 (3)	N2—C11—H11C	109.5
C5—C4—H4	120.4	H11A—C11—H11C	109.5
C3—C4—H4	120.4	H11B—C11—H11C	109.5
C4—C5—C6	121.6 (3)
O2—V1—O1—C1	70.1 (2)	V1—O1—C1—C6	27.6 (3)
O3—V1—O1—C1	−176.9 (2)	V1—O1—C1—C2	−153.33 (19)
N1—V1—O1—C1	−36.4 (2)	O1—C1—C2—C3	178.9 (2)
N2—V1—O1—C1	−72.2 (3)	C6—C1—C2—C3	−2.0 (4)
O2—V1—N1—C7	−74.6 (2)	C1—C2—C3—C4	0.6 (4)
O3—V1—N1—C7	124.8 (2)	C2—C3—C4—C5	1.0 (4)
O1—V1—N1—C7	29.8 (2)	C3—C4—C5—C6	−1.2 (4)
N2—V1—N1—C7	−165.1 (2)	O1—C1—C6—C5	−179.2 (2)
O2—V1—N1—C8	89.9 (2)	C2—C1—C6—C5	1.7 (3)
O3—V1—N1—C8	−70.6 (2)	O1—C1—C6—C7	2.9 (4)
O1—V1—N1—C8	−165.69 (19)	C2—C1—C6—C7	−176.2 (2)
N2—V1—N1—C8	−0.57 (18)	C4—C5—C6—C1	−0.1 (4)
O2—V1—N2—C11	41.3 (2)	C4—C5—C6—C7	177.8 (2)
O3—V1—N2—C11	−68.2 (2)	C8—N1—C7—C6	179.2 (2)
O1—V1—N2—C11	−174.9 (2)	V1—N1—C7—C6	−16.2 (4)
N1—V1—N2—C11	148.3 (2)	C1—C6—C7—N1	−6.3 (4)
O2—V1—N2—C9	−79.26 (18)	C5—C6—C7—N1	175.8 (2)
O3—V1—N2—C9	171.23 (19)	C7—N1—C8—C9	139.7 (2)
O1—V1—N2—C9	64.5 (3)	V1—N1—C8—C9	−26.0 (3)
N1—V1—N2—C9	27.70 (17)	C11—N2—C9—C8	−172.4 (2)
O2—V1—N2—C10	161.0 (2)	C10—N2—C9—C8	68.8 (3)
O3—V1—N2—C10	51.4 (2)	V1—N2—C9—C8	−50.9 (2)
O1—V1—N2—C10	−55.3 (3)	N1—C8—C9—N2	49.4 (3)
N1—V1—N2—C10	−92.1 (2)