The α polymorph of racemic tris­(2,4-penta­nedionato-κ2O,O′)vanadium(III), redetermined at 120 K

Kavitha, S.J.; Panchanatheswaran, K.; Low, J.N.; Glidewell, C.

doi:10.1107/S1600536805018441

metal-organic compounds

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ISSN: 2056-9890

Volume 61| Part 7| July 2005| Pages m1326-m1328

https://doi.org/10.1107/S1600536805018441

The α polymorph of racemic tris(2,4-pentanedionato-κ²O,O′)vanadium(III), redetermined at 120 K

S. Jose Kavitha,^a Krishnaswamy Panchanatheswaran,^a John N. Low ^b and Christopher Glidewell ^c ^*

^aSchool of Chemistry, Bharathidasan University, Tiruchirappalli, Tamil Nadu 620 024, India, ^bDepartment of Chemistry, University of Aberdeen, Meston Walk, Old Aberdeen AB24 3UE, Scotland, and ^cSchool of Chemistry, University of St Andrews, Fife KY16 9ST, Scotland
^*Correspondence e-mail: cg@st-andrews.ac.uk

(Received 8 June 2005; accepted 10 June 2005; online 17 June 2005)

In the α polymorph of the title compound, [V(C₅H₇O₂)₃], the molecules lie in general positions with no crystallographically imposed symmetry, but with approximate D₃ (32) molecular symmetry.

Comment

The title compound, (I) (Fig. 1), crystallizes in two structurally characterized polymorphs, an orthorhombic form in space group Pbca, denoted α, and a monoclinic form in space group P2₁/n, denoted β (Morosin & Montgomery, 1969 ). The orthorhombic α form has been structurally characterized only at ambient temperature (Morosin & Montgomery, 1969; Filgueiras et al., 2001 ), but neither report mentioned the molecular stereochemistry. We have now taken the opportunity to redetermine the structure of this phase using diffraction data collected at 120 K: the unit-cell dimensions and space group confirm that the same phase is present at 120 K as at ambient temperature.

In the α polymorph of compound (I) the molecules lie in general positions in space group Pbca, but the local molecular symmetry is very close to the ideal D₃ (32) expected for isolated molecules. Although the compound is racemic, the molecules are chiral, but the centrosymmetric space group accommodates equal numbers of the Λ and Δ enantiomorphs: the selected reference molecule (Fig. 1) has Λ configuration. The corresponding bond distances within the three independent ligands show some modest variation, as exemplified by the V—O and O—C distances (Table 1); likewise the ligand bite angles O—V—O within the rings show minor variation. While two of the three rings are effectively planar, that including atoms O11 and O13 shows a minor puckering, and this ring is best described as forming a boat conformer with a total puckering amplitude of 0.199 (2) Å, with the maximum displacement from the mean ring plane found for the V atom of 0.138 (2) Å.

Within each domain 0 < x < 0.5 and 0.5 < x < 1.0 there are four molecules, two of each enantiomer, with the Λ and Δ forms alternating, in chess-board fashion, on an approximately square grid (Fig. 2).

Figure 1
The Λ enantiomorph of compound (I)

in the α polymorph, showing the atom-labelling scheme. Displacement ellipsoids are drawn at the 30% probability level.

Figure 2
Projection on to (100) of the domain 0 < x < 0.5 in the α polymorph of compound (I)

, showing the alternation of Λ and Δ enantiomorphs. For the sake of clarity, the H atoms have been omitted. Atoms marked with an asterisk (*), a hash (#) or a dollar sign ($) are at the symmetry positions (x, $[{1\over 2}]$ − y, − $[{1\over 2}]$ + z), ( $[{1\over 2}]$ − x, $[{1\over 2}]$ + y, z) and ( $[{1\over 2}]$ − x, 1 − y, − $[{1\over 2}]$ + z), respectively.

Experimental

The title compound was prepared from VO(CH₃COCHCOCH₃)₂, according to the published procedure of Grdenić & Korpar-Čolig (1964 ), except that powdered tin was employed as the reducing agent rather than powdered zinc [m.p. 457 K; literature m.p. (Grdenić & Korpar-Čolig, 1964) 457 K].

Crystal data

[V(C₅H₇O₂)₃]
M_r = 348.26
Orthorhombic, P b c a
a = 13.3920 (7) Å
b = 16.4043 (6) Å
c = 15.1901 (10) Å
V = 3337.1 (3) Å³
Z = 8
D_x = 1.386 Mg m⁻³
Mo Kα radiation
Cell parameters from 3824 reflections
θ = 3.2–27.5°
μ = 0.62 mm⁻¹
T = 120 (2) K
Plate, brown
0.22 × 0.18 × 0.03 mm

Data collection

Bruker–Nonius KappaCCD diffractometer
φ and ω scans
Absorption correction: multi-scan(SADABS; Sheldrick, 2003 )T_min = 0.859, T_max = 0.982
30601 measured reflections
3824 independent reflections
1876 reflections with I > 2σ(I)
R_int = 0.174
θ_max = 27.5°
h = −17 → 17
k = −21 → 21
l = −19 → 18

Refinement

Refinement on F²
R[F² > 2σ(F²)] = 0.058
wR(F²) = 0.135
S = 1.00
3824 reflections
205 parameters
H-atom parameters constrained
w = 1/[σ²(F_o²) + (0.0529P)² + 0.2837P] where P = (F_o² + 2F_c²)/3
(Δ/σ)_max < 0.001
Δρ_max = 0.32 e Å⁻³
Δρ_min = −0.47 e Å⁻³

Table 1
Selected geometric parameters (Å, °)

V1—O11	1.998 (2)
V1—O13	1.983 (2)
V1—O21	1.971 (2)
V1—O23	2.006 (2)
V1—O31	1.986 (2)
V1—O33	1.959 (2)
C11—O11	1.272 (4)
C13—O13	1.279 (4)
C21—O21	1.283 (4)
C23—O23	1.263 (4)
C31—O31	1.271 (4)
C33—O33	1.284 (4)

O11—V1—O13	86.30 (10)
O21—V1—O23	88.35 (9)
O31—V1—O33	88.74 (9)

All H atoms were located in difference maps, and then treated as riding atoms, with C—H distances 0.95 Å and U_iso(H) = 1.2U_eq(C) for the ring CH atoms, and C—H distances 0.98 Å and U_iso(H) = 1.5U_eq(C) for the methyl groups.

Data collection: COLLECT (Hooft, 1999 ); cell refinement: DENZO (Otwinowski & Minor, 1997 ) and COLLECT; data reduction: DENZO and COLLECT; program(s) used to solve structure: OSCAIL (McArdle, 2003 ) and SHELXS97 (Sheldrick, 1997 ); program(s) used to refine structure: OSCAIL and SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003 ); software used to prepare material for publication: SHELXL97 and PRPKAPPA (Ferguson, 1999 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536805018441/lh6448sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536805018441/lh6448Isup2.hkl

Computing details top

Data collection: COLLECT (Hooft, 1999); cell refinement: DENZO (Otwinowski & Minor, 1997) and COLLECT; data reduction: DENZO and COLLECT; program(s) used to solve structure: OSCAIL (McArdle, 2003) and SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: OSCAIL and SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: SHELXL97 and PRPKAPPA (Ferguson, 1999).

α-Tris(2,4-pentanedionato-κ²O,O')vanadium(III) top

Crystal data top

[V(C₅H₇O₂)₃]	F(000) = 1456
M_r = 348.26	D_x = 1.386 Mg m⁻³
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 3824 reflections
a = 13.3920 (7) Å	θ = 3.2–27.5°
b = 16.4043 (6) Å	µ = 0.62 mm⁻¹
c = 15.1901 (10) Å	T = 120 K
V = 3337.1 (3) Å³	Plate, brown
Z = 8	0.22 × 0.18 × 0.03 mm

Data collection top

Bruker–Nonius 95mm CCD camera on κ goniostat diffractometer	3824 independent reflections
Radiation source: Bruker-Nonius FR91 rotating anode	1876 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.174
Detector resolution: 9.091 pixels mm^-1	θ_max = 27.5°, θ_min = 3.2°
π and ω scans	h = −17→17
Absorption correction: multi-scan (SADABS; Sheldrick, 2003)	k = −21→21
T_min = 0.859, T_max = 0.982	l = −19→18
30601 measured reflections

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)] = 0.058	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.135	H-atom parameters constrained
S = 1.00	w = 1/[σ²(F_o²) + (0.0529P)² + 0.2837P] where P = (F_o² + 2F_c²)/3
3824 reflections	(Δ/σ)_max < 0.001
205 parameters	Δρ_max = 0.32 e Å⁻³
0 restraints	Δρ_min = −0.47 e Å⁻³

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

	x	y	z	U_iso*/U_eq
V1	0.27195 (4)	0.25489 (3)	0.64183 (3)	0.02443 (18)
O11	0.18295 (16)	0.33275 (14)	0.70562 (13)	0.0298 (6)
O13	0.34058 (17)	0.35266 (14)	0.59448 (14)	0.0325 (6)
O21	0.19802 (16)	0.16706 (13)	0.70173 (14)	0.0302 (6)
O23	0.37185 (15)	0.25153 (14)	0.74014 (14)	0.0289 (5)
O31	0.17568 (16)	0.25354 (14)	0.54240 (13)	0.0298 (5)
O33	0.35710 (16)	0.17987 (14)	0.57521 (15)	0.0311 (6)
C11	0.1690 (3)	0.4085 (2)	0.6926 (2)	0.0333 (9)
C12	0.2281 (3)	0.4557 (2)	0.6374 (2)	0.0424 (10)
C13	0.3122 (3)	0.4271 (2)	0.5946 (2)	0.0351 (9)
C14	0.0859 (3)	0.4467 (2)	0.7451 (3)	0.0495 (11)
C15	0.3795 (3)	0.4855 (2)	0.5466 (3)	0.0515 (12)
C21	0.2160 (3)	0.1329 (2)	0.7760 (2)	0.0353 (9)
C22	0.2988 (3)	0.1485 (2)	0.8267 (3)	0.0396 (10)
C23	0.3745 (2)	0.2049 (2)	0.8063 (2)	0.0302 (8)
C24	0.1377 (3)	0.0738 (3)	0.8056 (3)	0.0565 (12)
C25	0.4643 (3)	0.2109 (2)	0.8651 (2)	0.0414 (10)
C31	0.1806 (3)	0.2154 (2)	0.4697 (2)	0.0306 (9)
C32	0.2614 (3)	0.1652 (2)	0.4453 (2)	0.0351 (9)
C33	0.3428 (3)	0.1500 (2)	0.4981 (2)	0.0325 (9)
C34	0.0925 (3)	0.2243 (2)	0.4089 (2)	0.0407 (10)
C35	0.4259 (3)	0.0943 (2)	0.4668 (3)	0.0453 (10)
H12	0.2096	0.5110	0.6286	0.051*
H14A	0.0265	0.4119	0.7423	0.074*
H14B	0.0701	0.5005	0.7207	0.074*
H14C	0.1069	0.4527	0.8066	0.074*
H15A	0.4405	0.4941	0.5809	0.077*
H15B	0.3450	0.5377	0.5387	0.077*
H15C	0.3967	0.4629	0.4888	0.077*
H22	0.3055	0.1188	0.8801	0.047*
H24A	0.0730	0.1016	0.8090	0.085*
H24B	0.1553	0.0524	0.8638	0.085*
H24C	0.1334	0.0287	0.7634	0.085*
H25A	0.5127	0.1688	0.8489	0.062*
H25B	0.4438	0.2031	0.9265	0.062*
H25C	0.4949	0.2648	0.8585	0.062*
H32	0.2595	0.1404	0.3888	0.042*
H34A	0.0439	0.1811	0.4213	0.061*
H34B	0.1149	0.2200	0.3477	0.061*
H34C	0.0611	0.2776	0.4183	0.061*
H35A	0.4906	0.1200	0.4784	0.068*
H35B	0.4188	0.0847	0.4034	0.068*
H35C	0.4221	0.0423	0.4982	0.068*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
V1	0.0213 (3)	0.0267 (3)	0.0253 (3)	0.0004 (3)	0.0020 (2)	0.0012 (3)
O11	0.0275 (14)	0.0328 (15)	0.0292 (13)	0.0027 (11)	0.0039 (11)	−0.0025 (11)
O13	0.0265 (15)	0.0313 (15)	0.0397 (15)	0.0002 (11)	0.0071 (11)	0.0062 (12)
O21	0.0240 (14)	0.0321 (14)	0.0344 (14)	−0.0060 (11)	−0.0020 (11)	0.0026 (12)
O23	0.0237 (13)	0.0328 (14)	0.0301 (12)	−0.0023 (12)	−0.0002 (10)	0.0028 (12)
O31	0.0219 (13)	0.0413 (14)	0.0263 (12)	0.0029 (12)	0.0021 (10)	−0.0020 (12)
O33	0.0272 (14)	0.0334 (14)	0.0328 (13)	0.0030 (11)	−0.0003 (11)	−0.0042 (11)
C11	0.030 (2)	0.036 (2)	0.034 (2)	0.0041 (18)	−0.0074 (17)	−0.0050 (18)
C12	0.049 (3)	0.029 (2)	0.049 (2)	0.007 (2)	0.001 (2)	0.009 (2)
C13	0.041 (2)	0.037 (2)	0.028 (2)	−0.0016 (19)	−0.0065 (17)	0.0070 (17)
C14	0.041 (3)	0.053 (3)	0.054 (2)	0.018 (2)	0.004 (2)	−0.011 (2)
C15	0.059 (3)	0.038 (2)	0.058 (3)	−0.012 (2)	0.003 (2)	0.015 (2)
C21	0.037 (2)	0.030 (2)	0.039 (2)	−0.0023 (18)	0.0025 (18)	0.0054 (17)
C22	0.039 (3)	0.038 (2)	0.041 (2)	−0.0022 (19)	−0.0074 (18)	0.0146 (19)
C23	0.025 (2)	0.036 (2)	0.030 (2)	0.0050 (17)	−0.0022 (16)	−0.0060 (18)
C24	0.054 (3)	0.060 (3)	0.056 (3)	−0.028 (2)	0.002 (2)	0.019 (2)
C25	0.028 (2)	0.058 (3)	0.037 (2)	0.0038 (19)	−0.0062 (17)	0.004 (2)
C31	0.026 (2)	0.039 (2)	0.027 (2)	−0.0084 (18)	0.0018 (16)	0.0032 (17)
C32	0.032 (2)	0.041 (2)	0.032 (2)	−0.0017 (19)	0.0025 (17)	−0.0097 (17)
C33	0.032 (2)	0.024 (2)	0.042 (2)	−0.0025 (17)	0.0081 (18)	−0.0029 (17)
C34	0.030 (2)	0.065 (3)	0.027 (2)	−0.0012 (19)	−0.0008 (16)	0.0005 (18)
C35	0.038 (3)	0.039 (2)	0.060 (3)	0.0076 (19)	0.004 (2)	−0.015 (2)

Geometric parameters (Å, º) top

V1—O11	1.998 (2)	C21—C22	1.375 (5)
V1—O13	1.983 (2)	C21—C24	1.497 (5)
V1—O21	1.971 (2)	C22—C23	1.407 (5)
V1—O23	2.006 (2)	C22—H22	0.95
V1—O31	1.986 (2)	C23—C25	1.502 (4)
V1—O33	1.959 (2)	C24—H24A	0.98
C11—O11	1.272 (4)	C24—H24B	0.98
C13—O13	1.279 (4)	C24—H24C	0.98
C21—O21	1.283 (4)	C25—H25A	0.98
C23—O23	1.263 (4)	C25—H25B	0.98
C31—O31	1.271 (4)	C25—H25C	0.98
C33—O33	1.284 (4)	C31—C32	1.409 (5)
C11—C12	1.387 (5)	C31—C34	1.506 (5)
C11—C14	1.507 (5)	C32—C33	1.377 (5)
C12—C13	1.383 (5)	C32—H32	0.95
C12—H12	0.95	C33—C35	1.516 (5)
C13—C15	1.504 (5)	C34—H34A	0.98
C14—H14A	0.98	C34—H34B	0.98
C14—H14B	0.98	C34—H34C	0.98
C14—H14C	0.98	C35—H35A	0.98
C15—H15A	0.98	C35—H35B	0.98
C15—H15B	0.98	C35—H35C	0.98
C15—H15C	0.98

O33—V1—O21	94.10 (10)	C21—C22—C23	125.5 (3)
O33—V1—O13	92.92 (10)	C21—C22—H22	117.3
O21—V1—O13	172.45 (10)	C23—C22—H22	117.3
O21—V1—O31	90.96 (9)	O23—C23—C22	123.6 (3)
O13—V1—O31	91.96 (10)	O23—C23—C25	117.1 (3)
O33—V1—O11	177.91 (9)	C22—C23—C25	119.3 (3)
O21—V1—O11	86.78 (9)	C23—O23—V1	128.9 (2)
O11—V1—O13	86.30 (10)	C21—C24—H24A	109.5
O31—V1—O11	89.35 (9)	C21—C24—H24B	109.5
O33—V1—O23	88.80 (9)	H24A—C24—H24B	109.5
O21—V1—O23	88.35 (9)	C21—C24—H24C	109.5
O31—V1—O33	88.74 (9)	H24A—C24—H24C	109.5
O13—V1—O23	89.03 (9)	H24B—C24—H24C	109.5
O31—V1—O23	177.39 (10)	C23—C25—H25A	109.5
O11—V1—O23	93.12 (9)	C23—C25—H25B	109.5
O11—C11—C12	123.7 (3)	H25A—C25—H25B	109.5
O11—C11—C14	115.6 (3)	C23—C25—H25C	109.5
C12—C11—C14	120.6 (3)	H25A—C25—H25C	109.5
C11—O11—V1	129.5 (2)	H25B—C25—H25C	109.5
C13—C12—C11	124.0 (3)	O31—C31—C32	123.8 (3)
C13—C12—H12	118.0	O31—C31—C34	116.4 (3)
C11—C12—H12	118.0	C32—C31—C34	119.8 (3)
O13—C13—C12	124.5 (3)	C31—O31—V1	129.2 (2)
O13—C13—C15	115.4 (3)	C33—C32—C31	124.1 (3)
C12—C13—C15	120.0 (4)	C33—C32—H32	117.9
C13—O13—V1	129.3 (2)	C31—C32—H32	117.9
C11—C14—H14A	109.5	O33—C33—C32	125.4 (3)
C11—C14—H14B	109.5	O33—C33—C35	114.0 (3)
H14A—C14—H14B	109.5	C32—C33—C35	120.5 (3)
C11—C14—H14C	109.5	C33—O33—V1	128.7 (2)
H14A—C14—H14C	109.5	C31—C34—H34A	109.5
H14B—C14—H14C	109.5	C31—C34—H34B	109.5
C13—C15—H15A	109.5	H34A—C34—H34B	109.5
C13—C15—H15B	109.5	C31—C34—H34C	109.5
H15A—C15—H15B	109.5	H34A—C34—H34C	109.5
C13—C15—H15C	109.5	H34B—C34—H34C	109.5
H15A—C15—H15C	109.5	C33—C35—H35A	109.5
H15B—C15—H15C	109.5	C33—C35—H35B	109.5
O21—C21—C22	124.2 (3)	H35A—C35—H35B	109.5
O21—C21—C24	114.6 (3)	C33—C35—H35C	109.5
C22—C21—C24	121.2 (3)	H35A—C35—H35C	109.5
C21—O21—V1	129.2 (2)	H35B—C35—H35C	109.5

C12—C11—O11—V1	−11.0 (5)	C21—C22—C23—O23	4.2 (6)
C14—C11—O11—V1	172.0 (2)	C21—C22—C23—C25	−175.6 (4)
O21—V1—O11—C11	−166.3 (3)	C22—C23—O23—V1	−5.6 (5)
O13—V1—O11—C11	16.7 (3)	C25—C23—O23—V1	174.2 (2)
O31—V1—O11—C11	−75.3 (3)	O33—V1—O23—C23	−92.0 (3)
O23—V1—O11—C11	105.5 (3)	O21—V1—O23—C23	2.1 (3)
O11—C11—C12—C13	−4.1 (6)	O13—V1—O23—C23	175.1 (3)
C14—C11—C12—C13	172.7 (3)	O11—V1—O23—C23	88.8 (3)
C11—C12—C13—O13	6.3 (6)	C32—C31—O31—V1	−1.0 (5)
C11—C12—C13—C15	−171.3 (3)	C34—C31—O31—V1	177.4 (2)
C12—C13—O13—V1	6.8 (5)	O33—V1—O31—C31	−0.2 (3)
C15—C13—O13—V1	−175.5 (2)	O21—V1—O31—C31	−94.2 (3)
O33—V1—O13—C13	163.6 (3)	O13—V1—O31—C31	92.7 (3)
O31—V1—O13—C13	74.8 (3)	O11—V1—O31—C31	179.0 (3)
O11—V1—O13—C13	−14.5 (3)	O31—C31—C32—C33	1.8 (6)
O23—V1—O13—C13	−107.6 (3)	C34—C31—C32—C33	−176.6 (3)
C22—C21—O21—V1	−5.2 (5)	C31—C32—C33—O33	−1.1 (6)
C24—C21—O21—V1	174.0 (3)	C31—C32—C33—C35	179.3 (3)
O33—V1—O21—C21	91.9 (3)	C32—C33—O33—V1	−0.3 (5)
O31—V1—O21—C21	−179.3 (3)	C35—C33—O33—V1	179.3 (2)
O11—V1—O21—C21	−90.0 (3)	O21—V1—O33—C33	91.6 (3)
O23—V1—O21—C21	3.2 (3)	O13—V1—O33—C33	−91.1 (3)
O21—C21—C22—C23	1.4 (6)	O31—V1—O33—C33	0.8 (3)
C24—C21—C22—C23	−177.6 (4)	O23—V1—O33—C33	179.9 (3)

Acknowledgements

X-ray data were collected at the EPSRC X-ray Crystallographic Service, University of Southampton, England. The authors thank the staff for all their help and advice.

References

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Volume 61| Part 7| July 2005| Pages m1326-m1328

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