trans-Bis(1,3-diphenyl­propane-1,3-dionato)(methanol)oxidovanadium(IV) methanol disolvate

Pretorius, C.; Venter, J.A.; Roodt, A.

doi:10.1107/S1600536812044686

metal-organic compounds

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ISSN: 2056-9890

Volume 68| Part 12| December 2012| Pages m1442-m1443

doi:10.1107/S1600536812044686

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trans-Bis(1,3-diphenylpropane-1,3-dionato)(methanol)oxidovanadium(IV) methanol disolvate

Carla Pretorius,^a ^* Johan A. Venter ^a and Andreas Roodt ^a

^aDepartment of Chemistry, University of the Free State, PO Box 339, Bloemfontein 9300, South Africa
^*Correspondence e-mail: CPretorius@ufs.ac.za

(Received 25 September 2012; accepted 29 October 2012; online 3 October 2012)

In the title compound, [V(C₁₅H₁₁O₂)₂O(CH₃OH)]·2CH₃OH, the V^IV atom is coordinated by two 1,3-diphenylpropane-1,3-dionate ligands and an oxide ligand in an axial position. The sixth position is occupied by the O atom of a methanol group bonded trans to the oxide atom. The octahedral geometry is significantly distorted, with the V^IV atom lying 0.330 (3) Å above the equatorial plane formed by the O atoms of the two β-diketonate ligands. In the crystal, O—H⋯O hydrogen bonds between the coordinating methanol group in the complex and the two methanol solvent molecules lead to the formation of polymeric chains along the c-axis direction. Weak C—H⋯O contacts are also observed.

Related literature

For synthetic background, see: Schilde et al. (1995 ). For other methanol-substituted vanadium complexes, see: Gao et al. (1998 ); Chen et al. (2004 ); Tasiopoulos et al. (1999 ). For methoxy-substituted vanadium complexes, see: Bansse et al. (1992 ).

Experimental

Crystal data

[V(C₁₅H₁₁O₂)₂O(CH₄O)]·2CH₄O
M_r = 609.54
Monoclinic, P 2₁ /c
a = 16.1411 (1) Å
b = 10.7450 (6) Å
c = 18.5378 (13) Å
β = 113.579 (2)°
V = 2946.7 (3) Å³
Z = 4
Mo Kα radiation
μ = 0.39 mm⁻¹
T = 100 K
0.47 × 0.07 × 0.05 mm

Data collection

Bruker APEXII KappaCCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2008 ) T_min = 0.968, T_max = 0.981
38614 measured reflections
7317 independent reflections
5545 reflections with I > 2σ(I)
R_int = 0.046

Refinement

R[F² > 2σ(F²)] = 0.041
wR(F²) = 0.102
S = 1.03
7317 reflections
412 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.45 e Å⁻³
Δρ_min = −0.43 e Å⁻³

Table 1
Selected bond lengths (Å)

O1—V1	1.5965 (13)
O2—V1	1.9972 (12)
O3—V1	2.0045 (12)
O4—V1	1.9847 (12)
O5—V1	1.9935 (12)
O6—V1	2.3020 (15)

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O6—H6A⋯O7	0.82 (3)	1.83 (3)	2.644 (2)	169 (3)
O7—H7A⋯O8ⁱ	0.87 (3)	1.90 (3)	2.749 (2)	168 (3)
O8—H8A⋯O3	0.90 (3)	1.96 (3)	2.853 (2)	178 (3)
C13—H13⋯O1ⁱⁱ	0.95	2.58	3.487 (2)	160
C32—H32B⋯O1ⁱ	0.98 (3)	2.43 (3)	3.360 (3)	159 (2)
Symmetry codes: (i) $[x, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ ; (ii) $[-x+1, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

Data collection: APEX2 (Bruker, 2011 ); cell refinement: SAINT-Plus (Bruker, 2008); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: Mercury (Macrae et al., 2008 ); software used to prepare material for publication: WinGX (Farrugia, 1999 ), publCIF (Westrip, 2010 ), PARST (Nardelli, 1995 ) and PLATON (Spek, 2009 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536812044686/sj5267sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812044686/sj5267Isup2.hkl

checkCIF report

Comment top

The complex has two coordinated 1,3-diphenylpropane-1,3-dionato (dbm) ligands in the equatorial plane, the same as in the [VO(dbm)₂] structure described by Schilde (Schilde et al., 1995). The oxido group is in the axial position and no significant change in bond length is reported for the O1—V1 bond of 1.5964 (3) Å as compared to the [VO(dbm)₂] structure (1.5922 (4) Å). The sixth coordination position at the vanadium centre trans to the oxido is occupied by a methanol molecule. The rather long bond length of 2.302 (2) Å is similar to methanol coordination in structures by Gao (2.346 Å) (Gao et al., 1998), Chen (2.333 Å) (Chen et al., 2004) and Tasiopoulos (2.301 Å) (Tasiopoulos et al., 1999). A methoxy group bonded to a vanadium metal centre would have a V-OMe bond length of approximately 1.755 Å (Bansse et al., 1992).

Intermolecular O6—H6A···O7 hydrogen bonding in the order of 2.644 (2) Å was observed with a methanol solvent molecule. Additional intermolecular hydrogen bonding was also noted between O7—H7A···O8ⁱ of the order 2.749 (2) Å and O8—H8A···O3 in the order of 2.853 (2) Å. These interactions eventually lead to the formation of polymeric chains of the complex along the c-axis, as illustrated in Figure 2.

Weaker intermolecular hydrogen bonding was also noted between C13—H13···O1ⁱⁱ in the order of 3.487 (2) Å and C32—H32B···O1ⁱ in the order of 3.360 (3) Å.

Related literature top

For synthetic background, see: Schilde et al. (1995). For other methanol-substituted vanadium complexes, see: Gao et al. (1998); Chen et al. (2004); Tasiopoulos et al. (1999). For methoxy-substituted vanadium complexes, see: Bansse et al. (1992).

Experimental top

V₂O₅ (1.0 g, 5.5 mmol) was added to a mixture of ethanol, water and sulfuric acid (5 cm³, 2 cm³ and 2 cm³ respectively) and refluxed for one hour, after which the yellow mixture turned a brilliant blue colour. A solution of 1,3-diphenylpropane-1,3-dione (4.93 g, 22 mmol) in ethanol (10 cm³) was added to the reaction mixture which was then stirred for ca 10 min. A saturated solution of sodium carbonate in water (20 cm³) was added to the mixture and the resulting green precipitate was collected by filtration. The precipitate was recrystallized from methanol and, after two weeks, small red needle-like crystals of [VO(dbm)₂(MeOH)] were formed (yield: 2.35 g, 70%).

Computing details top

Data collection: APEX2 (Bruker, 2011); cell refinement: SAINT-Plus (Bruker, 2008); data reduction: SAINT-Plus (Bruker, 2008); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: Mercury (Macrae et al., 2008); software used to prepare material for publication: WinGX (Farrugia, 1999), publCIF (Westrip, 2010), PARST (Nardelli, 1995) and PLATON (Spek, 2009).

Figures top

	Fig. 1. Molecular structure of the title compound. Displacement ellipsoids are drawn at the 50% probability displacement level. Solvent molecules have been omitted for clarity.
	Fig. 2. Hydrogen bonds (indicated in blue) linking one of the compound molecules and a solvent molecule leads to the formation of polymeric chains of the compound along the c-axis.

trans-Bis(1,3-diphenylpropane-1,3-dionato)(methanol)oxidovanadium(IV) methanol disolvate top

Crystal data top

[V(C₁₅H₁₁O₂)₂O(CH₄O)]·2CH₄O	F(000) = 1276
M_r = 609.54	D_x = 1.374 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 7652 reflections
a = 16.1411 (1) Å	θ = 2.2–27.7°
b = 10.7450 (6) Å	µ = 0.39 mm⁻¹
c = 18.5378 (13) Å	T = 100 K
β = 113.579 (2)°	Needle, red
V = 2946.7 (3) Å³	0.47 × 0.07 × 0.05 mm
Z = 4

Data collection top

Bruker APEXII KappaCCD diffractometer	7317 independent reflections
Radiation source: fine-focus sealed tube	5545 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.046
Detector resolution: 512 pixels mm^-1	θ_max = 28.3°, θ_min = 2.2°
ϕ and ω scans	h = −21→21
Absorption correction: multi-scan (SADABS; Bruker, 2008)	k = −14→8
T_min = 0.968, T_max = 0.981	l = −24→24
38614 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)] = 0.041	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.102	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ²(F_o²) + (0.0383P)² + 2.0104P] where P = (F_o² + 2F_c²)/3
7317 reflections	(Δ/σ)_max = 0.001
412 parameters	Δρ_max = 0.45 e Å⁻³
0 restraints	Δρ_min = −0.43 e Å⁻³
0 constraints

Crystal data top

[V(C₁₅H₁₁O₂)₂O(CH₄O)]·2CH₄O	V = 2946.7 (3) Å³
M_r = 609.54	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 16.1411 (1) Å	µ = 0.39 mm⁻¹
b = 10.7450 (6) Å	T = 100 K
c = 18.5378 (13) Å	0.47 × 0.07 × 0.05 mm
β = 113.579 (2)°

Data collection top

Bruker APEXII KappaCCD diffractometer	7317 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2008)	5545 reflections with I > 2σ(I)
T_min = 0.968, T_max = 0.981	R_int = 0.046
38614 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.041	0 restraints
wR(F²) = 0.102	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	Δρ_max = 0.45 e Å⁻³
7317 reflections	Δρ_min = −0.43 e Å⁻³
412 parameters

Special details top

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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
C1	0.36765 (12)	0.39961 (16)	0.05770 (10)	0.0162 (4)
C2	0.43706 (12)	0.32029 (17)	0.10546 (11)	0.0173 (4)
C3	0.42559 (12)	0.20489 (16)	0.13327 (10)	0.0169 (4)
C4	0.39167 (12)	0.52183 (16)	0.03351 (11)	0.0167 (4)
C5	0.33514 (12)	0.57289 (17)	−0.03831 (11)	0.0200 (4)
H5	0.2826	0.529	−0.0715	0.024*
C6	0.35509 (13)	0.68762 (17)	−0.06167 (12)	0.0226 (4)
H6	0.3166	0.7219	−0.111	0.027*
C7	0.43106 (13)	0.75208 (17)	−0.01303 (12)	0.0234 (4)
H7	0.4441	0.8312	−0.0288	0.028*
C8	0.48820 (13)	0.70229 (17)	0.05840 (12)	0.0246 (4)
H8	0.5405	0.7469	0.0913	0.03*
C9	0.46897 (13)	0.58668 (17)	0.08203 (11)	0.0218 (4)
H9	0.5082	0.552	0.1309	0.026*
C10	0.50605 (12)	0.12914 (17)	0.18099 (10)	0.0177 (4)
C11	0.58991 (13)	0.18430 (19)	0.22357 (11)	0.0226 (4)
H11	0.5958	0.2723	0.2241	0.027*
C12	0.66476 (13)	0.1110 (2)	0.26513 (12)	0.0274 (5)
H12	0.7216	0.1492	0.2937	0.033*
C13	0.65718 (14)	−0.0174 (2)	0.26531 (12)	0.0278 (5)
H13	0.7086	−0.0672	0.2938	0.033*
C14	0.57377 (14)	−0.07296 (19)	0.22355 (12)	0.0252 (4)
H14	0.5682	−0.161	0.2236	0.03*
C15	0.49862 (13)	−0.00043 (17)	0.18183 (11)	0.0205 (4)
H15	0.4418	−0.0391	0.1537	0.025*
C16	0.11816 (12)	−0.00936 (16)	−0.01969 (11)	0.0161 (4)
C17	0.05536 (12)	0.05557 (16)	−0.08338 (11)	0.0179 (4)
C18	0.05763 (12)	0.18349 (16)	−0.09553 (10)	0.0159 (4)
C19	0.11005 (12)	−0.14649 (16)	−0.01373 (10)	0.0157 (4)
C20	0.18785 (12)	−0.21569 (16)	0.02779 (10)	0.0172 (4)
H20	0.2441	−0.1745	0.0539	0.021*
C21	0.18344 (13)	−0.34458 (17)	0.03109 (11)	0.0191 (4)
H21	0.2367	−0.3911	0.0592	0.023*
C22	0.10189 (13)	−0.40532 (17)	−0.00637 (11)	0.0209 (4)
H22	0.0993	−0.4936	−0.0049	0.025*
C23	0.02358 (13)	−0.33711 (17)	−0.04628 (11)	0.0213 (4)
H23	−0.0327	−0.3787	−0.0711	0.026*
C24	0.02754 (12)	−0.20826 (16)	−0.04996 (11)	0.0178 (4)
H24	−0.0261	−0.162	−0.0772	0.021*
C25	−0.01309 (12)	0.24140 (16)	−0.16673 (11)	0.0173 (4)
C26	−0.05067 (12)	0.17798 (17)	−0.23829 (11)	0.0200 (4)
H26	−0.0338	0.0942	−0.2417	0.024*
C27	−0.11255 (13)	0.23700 (19)	−0.30452 (11)	0.0237 (4)
H27	−0.1369	0.1943	−0.3534	0.028*
C28	−0.13888 (13)	0.35818 (19)	−0.29931 (12)	0.0253 (4)
H28	−0.1816	0.3982	−0.3446	0.03*
C29	−0.10314 (13)	0.42114 (18)	−0.22823 (12)	0.0255 (4)
H29	−0.1222	0.5036	−0.2245	0.031*
C30	−0.03947 (12)	0.36340 (17)	−0.16254 (11)	0.0211 (4)
H30	−0.0137	0.4076	−0.1142	0.025*
C31	0.33537 (13)	0.05156 (17)	−0.04292 (12)	0.0227 (4)
H31A	0.3045	−0.0252	−0.0393	0.034*
H31B	0.3928	0.0584	0.0031	0.034*
H31C	0.3471	0.0497	−0.0909	0.034*
C32	0.17157 (17)	0.2844 (3)	−0.21685 (16)	0.0405 (6)
C33	0.24944 (16)	−0.0441 (2)	0.22012 (13)	0.0351 (5)
H33A	0.2382	−0.078	0.2645	0.053*
H33B	0.264	−0.1122	0.192	0.053*
H33C	0.1953	−0.0006	0.1842	0.053*
O1	0.19196 (8)	0.26454 (12)	0.11198 (8)	0.0212 (3)
O2	0.28326 (8)	0.37464 (11)	0.03141 (7)	0.0186 (3)
O3	0.34775 (8)	0.15408 (11)	0.11931 (7)	0.0182 (3)
O4	0.18704 (8)	0.04098 (11)	0.03497 (7)	0.0188 (3)
O5	0.11722 (8)	0.25860 (11)	−0.04987 (7)	0.0181 (3)
O6	0.27966 (9)	0.15603 (13)	−0.04550 (8)	0.0239 (3)
O7	0.26609 (11)	0.29178 (17)	−0.16870 (10)	0.0416 (4)
O8	0.32366 (10)	0.04114 (15)	0.24890 (9)	0.0311 (3)
V1	0.22608 (2)	0.21767 (3)	0.046818 (18)	0.01557 (9)
H2	0.4932 (14)	0.3447 (18)	0.1177 (11)	0.017 (5)*
H6A	0.2815 (17)	0.203 (2)	−0.0798 (15)	0.041 (7)*
H7A	0.2918 (18)	0.340 (3)	−0.1908 (16)	0.052 (8)*
H8A	0.3325 (19)	0.078 (3)	0.2091 (18)	0.065 (9)*
H17	0.0095 (13)	0.0099 (18)	−0.1201 (12)	0.018 (5)*
H32A	0.1461 (18)	0.210 (2)	−0.1987 (15)	0.049 (7)*
H32B	0.1601 (19)	0.273 (3)	−0.2725 (19)	0.066 (9)*
H32C	0.1388 (17)	0.365 (2)	−0.2115 (15)	0.045 (7)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0170 (9)	0.0157 (8)	0.0157 (9)	−0.0014 (7)	0.0065 (7)	−0.0038 (7)
C2	0.0115 (9)	0.0199 (9)	0.0188 (9)	−0.0003 (7)	0.0044 (7)	−0.0004 (7)
C3	0.0156 (9)	0.0194 (9)	0.0144 (9)	0.0002 (7)	0.0049 (7)	−0.0023 (7)
C4	0.0149 (9)	0.0147 (8)	0.0223 (9)	0.0013 (7)	0.0091 (8)	−0.0006 (7)
C5	0.0154 (9)	0.0204 (9)	0.0238 (10)	−0.0005 (7)	0.0074 (8)	−0.0007 (8)
C6	0.0203 (10)	0.0221 (9)	0.0266 (10)	0.0050 (8)	0.0107 (8)	0.0062 (8)
C7	0.0243 (10)	0.0169 (9)	0.0342 (11)	0.0005 (8)	0.0173 (9)	0.0025 (8)
C8	0.0222 (10)	0.0211 (9)	0.0301 (11)	−0.0057 (8)	0.0100 (9)	−0.0044 (8)
C9	0.0216 (10)	0.0208 (9)	0.0203 (10)	−0.0014 (8)	0.0056 (8)	−0.0010 (7)
C10	0.0161 (9)	0.0209 (9)	0.0155 (9)	0.0028 (7)	0.0057 (7)	0.0029 (7)
C11	0.0199 (10)	0.0251 (9)	0.0197 (10)	0.0005 (8)	0.0046 (8)	0.0049 (8)
C12	0.0173 (10)	0.0373 (12)	0.0226 (10)	0.0020 (9)	0.0027 (8)	0.0070 (9)
C13	0.0238 (10)	0.0364 (11)	0.0225 (10)	0.0135 (9)	0.0086 (9)	0.0113 (9)
C14	0.0306 (11)	0.0234 (10)	0.0227 (10)	0.0067 (8)	0.0119 (9)	0.0064 (8)
C15	0.0201 (9)	0.0225 (9)	0.0172 (9)	0.0014 (8)	0.0057 (8)	0.0020 (7)
C16	0.0137 (8)	0.0160 (8)	0.0189 (9)	−0.0006 (7)	0.0070 (7)	−0.0018 (7)
C17	0.0162 (9)	0.0159 (8)	0.0178 (9)	−0.0017 (7)	0.0028 (8)	−0.0024 (7)
C18	0.0136 (8)	0.0189 (8)	0.0149 (9)	0.0012 (7)	0.0053 (7)	−0.0017 (7)
C19	0.0180 (9)	0.0145 (8)	0.0148 (9)	0.0004 (7)	0.0067 (7)	0.0000 (7)
C20	0.0156 (9)	0.0186 (8)	0.0160 (9)	−0.0013 (7)	0.0049 (7)	−0.0009 (7)
C21	0.0200 (9)	0.0187 (9)	0.0199 (9)	0.0055 (7)	0.0091 (8)	0.0037 (7)
C22	0.0270 (10)	0.0147 (8)	0.0224 (10)	−0.0009 (8)	0.0112 (8)	0.0015 (7)
C23	0.0208 (9)	0.0192 (9)	0.0238 (10)	−0.0042 (8)	0.0090 (8)	−0.0010 (8)
C24	0.0167 (9)	0.0182 (8)	0.0180 (9)	0.0016 (7)	0.0065 (7)	0.0006 (7)
C25	0.0142 (9)	0.0178 (8)	0.0176 (9)	−0.0004 (7)	0.0040 (7)	0.0016 (7)
C26	0.0178 (9)	0.0194 (9)	0.0213 (10)	−0.0010 (7)	0.0064 (8)	−0.0011 (7)
C27	0.0181 (10)	0.0332 (11)	0.0166 (9)	−0.0029 (8)	0.0036 (8)	0.0004 (8)
C28	0.0179 (9)	0.0318 (11)	0.0222 (10)	0.0022 (8)	0.0038 (8)	0.0095 (8)
C29	0.0223 (10)	0.0201 (9)	0.0296 (11)	0.0048 (8)	0.0058 (9)	0.0061 (8)
C30	0.0192 (9)	0.0196 (9)	0.0203 (10)	0.0002 (7)	0.0036 (8)	0.0001 (7)
C31	0.0214 (10)	0.0191 (9)	0.0273 (10)	0.0017 (8)	0.0095 (8)	−0.0016 (8)
C32	0.0373 (14)	0.0536 (16)	0.0319 (13)	−0.0119 (12)	0.0153 (11)	−0.0011 (12)
C33	0.0395 (13)	0.0309 (11)	0.0319 (12)	−0.0014 (10)	0.0111 (10)	0.0019 (9)
O1	0.0164 (6)	0.0228 (7)	0.0219 (7)	−0.0014 (5)	0.0050 (6)	−0.0022 (5)
O2	0.0136 (6)	0.0157 (6)	0.0228 (7)	−0.0008 (5)	0.0035 (5)	−0.0003 (5)
O3	0.0140 (6)	0.0173 (6)	0.0200 (7)	−0.0010 (5)	0.0034 (5)	0.0016 (5)
O4	0.0170 (6)	0.0152 (6)	0.0184 (7)	−0.0024 (5)	0.0009 (5)	0.0010 (5)
O5	0.0153 (6)	0.0155 (6)	0.0188 (7)	−0.0003 (5)	0.0019 (5)	−0.0004 (5)
O6	0.0289 (8)	0.0198 (7)	0.0249 (7)	0.0063 (6)	0.0129 (6)	0.0057 (6)
O7	0.0356 (9)	0.0487 (10)	0.0377 (10)	−0.0030 (8)	0.0115 (8)	0.0180 (8)
O8	0.0288 (8)	0.0391 (9)	0.0259 (8)	0.0001 (7)	0.0113 (7)	0.0019 (7)
V1	0.01259 (15)	0.01394 (14)	0.01701 (16)	−0.00089 (12)	0.00259 (12)	−0.00022 (12)

Geometric parameters (Å, º) top

C1—O2	1.278 (2)	C21—C22	1.382 (3)
C1—C2	1.404 (2)	C21—H21	0.95
C1—C4	1.488 (2)	C22—C23	1.391 (3)
C2—C3	1.383 (3)	C22—H22	0.95
C2—H2	0.88 (2)	C23—C24	1.389 (2)
C3—O3	1.298 (2)	C23—H23	0.95
C3—O3	1.298 (2)	C24—H24	0.95
C3—C10	1.487 (2)	C25—C30	1.390 (2)
C4—C5	1.391 (3)	C25—C26	1.396 (3)
C4—C9	1.398 (3)	C26—C27	1.388 (3)
C5—C6	1.387 (3)	C26—H26	0.95
C5—H5	0.95	C27—C28	1.385 (3)
C6—C7	1.383 (3)	C27—H27	0.95
C6—H6	0.95	C28—C29	1.385 (3)
C7—C8	1.383 (3)	C28—H28	0.95
C7—H7	0.95	C29—C30	1.387 (3)
C8—C9	1.393 (3)	C29—H29	0.95
C8—H8	0.95	C30—H30	0.95
C9—H9	0.95	C31—O6	1.427 (2)
C10—C11	1.397 (3)	C31—H31A	0.98
C10—C15	1.398 (2)	C31—H31B	0.98
C11—C12	1.389 (3)	C31—H31C	0.98
C11—H11	0.95	C32—O7	1.429 (3)
C12—C13	1.385 (3)	C32—O7	1.429 (3)
C12—H12	0.95	C32—H32A	1.02 (3)
C13—C14	1.391 (3)	C32—H32B	0.98 (3)
C13—H13	0.95	C32—H32C	1.04 (3)
C14—C15	1.388 (3)	C33—O8	1.431 (3)
C14—H14	0.95	C33—H33A	0.98
C15—H15	0.95	C33—H33B	0.98
C16—O4	1.286 (2)	C33—H33C	0.98
C16—C17	1.397 (2)	O1—V1	1.5965 (13)
C16—C19	1.487 (2)	O2—V1	1.9972 (12)
C17—C18	1.396 (2)	O3—V1	2.0045 (12)
C17—H17	0.92 (2)	O4—V1	1.9847 (12)
C18—O5	1.281 (2)	O5—V1	1.9935 (12)
C18—C25	1.492 (2)	O6—V1	2.3020 (15)
C19—C20	1.396 (2)	O6—H6A	0.82 (3)
C19—C24	1.396 (2)	O7—H7A	0.87 (3)
C20—C21	1.389 (2)	O8—H8A	0.90 (3)
C20—H20	0.95	V1—O3	2.0045 (12)

O2—C1—C2	124.94 (16)	C23—C24—H24	119.9
O2—C1—C4	115.89 (15)	C19—C24—H24	119.9
C2—C1—C4	119.16 (16)	C30—C25—C26	119.14 (17)
C3—C2—C1	125.94 (17)	C30—C25—C18	119.14 (16)
C3—C2—H2	116.6 (13)	C26—C25—C18	121.66 (16)
C1—C2—H2	117.4 (13)	C27—C26—C25	120.20 (17)
O3—C3—C2	124.48 (16)	C27—C26—H26	119.9
O3—C3—C2	124.48 (16)	C25—C26—H26	119.9
O3—C3—C10	115.71 (15)	C28—C27—C26	120.01 (18)
O3—C3—C10	115.71 (15)	C28—C27—H27	120
C2—C3—C10	119.79 (16)	C26—C27—H27	120
C5—C4—C9	119.63 (17)	C27—C28—C29	120.19 (18)
C5—C4—C1	119.09 (16)	C27—C28—H28	119.9
C9—C4—C1	121.27 (16)	C29—C28—H28	119.9
C6—C5—C4	120.29 (17)	C28—C29—C30	119.81 (18)
C6—C5—H5	119.9	C28—C29—H29	120.1
C4—C5—H5	119.9	C30—C29—H29	120.1
C7—C6—C5	119.86 (18)	C29—C30—C25	120.60 (18)
C7—C6—H6	120.1	C29—C30—H30	119.7
C5—C6—H6	120.1	C25—C30—H30	119.7
C6—C7—C8	120.56 (18)	O6—C31—H31A	109.5
C6—C7—H7	119.7	O6—C31—H31B	109.5
C8—C7—H7	119.7	H31A—C31—H31B	109.5
C7—C8—C9	119.92 (18)	O6—C31—H31C	109.5
C7—C8—H8	120	H31A—C31—H31C	109.5
C9—C8—H8	120	H31B—C31—H31C	109.5
C8—C9—C4	119.74 (18)	O7—C32—H32A	108.0 (15)
C8—C9—H9	120.1	O7—C32—H32A	108.0 (15)
C4—C9—H9	120.1	O7—C32—H32B	111.6 (17)
C11—C10—C15	118.96 (17)	O7—C32—H32B	111.6 (17)
C11—C10—C3	121.47 (16)	H32A—C32—H32B	109 (2)
C15—C10—C3	119.55 (16)	O7—C32—H32C	110.7 (14)
C12—C11—C10	120.26 (18)	O7—C32—H32C	110.7 (14)
C12—C11—H11	119.9	H32A—C32—H32C	110 (2)
C10—C11—H11	119.9	H32B—C32—H32C	108 (2)
C13—C12—C11	120.54 (19)	O8—C33—H33A	109.5
C13—C12—H12	119.7	O8—C33—H33B	109.5
C11—C12—H12	119.7	H33A—C33—H33B	109.5
C12—C13—C14	119.54 (18)	O8—C33—H33C	109.5
C12—C13—H13	120.2	H33A—C33—H33C	109.5
C14—C13—H13	120.2	H33B—C33—H33C	109.5
C15—C14—C13	120.31 (18)	C1—O2—V1	127.28 (11)
C15—C14—H14	119.8	C3—O3—V1	126.95 (11)
C13—C14—H14	119.8	C16—O4—V1	128.73 (11)
C14—C15—C10	120.38 (18)	C18—O5—V1	127.87 (11)
C14—C15—H15	119.8	C31—O6—V1	128.35 (12)
C10—C15—H15	119.8	C31—O6—H6A	107.1 (18)
O4—C16—C17	124.21 (16)	V1—O6—H6A	122.5 (18)
O4—C16—C19	115.61 (15)	C32—O7—H7A	109.3 (18)
C17—C16—C19	120.13 (16)	C33—O8—H8A	111.0 (19)
C18—C17—C16	124.84 (17)	O1—V1—O4	101.25 (6)
C18—C17—H17	118.1 (12)	O1—V1—O5	99.43 (6)
C16—C17—H17	117.1 (12)	O4—V1—O5	89.13 (5)
O5—C18—C17	125.10 (16)	O1—V1—O2	99.25 (6)
O5—C18—C25	115.35 (15)	O4—V1—O2	159.47 (6)
C17—C18—C25	119.55 (16)	O5—V1—O2	88.66 (5)
C20—C19—C24	119.11 (16)	O1—V1—O3	98.18 (6)
C20—C19—C16	118.82 (16)	O4—V1—O3	86.02 (5)
C24—C19—C16	122.05 (16)	O5—V1—O3	162.32 (5)
C21—C20—C19	120.30 (17)	O2—V1—O3	89.94 (5)
C21—C20—H20	119.8	O1—V1—O3	98.18 (6)
C19—C20—H20	119.8	O4—V1—O3	86.02 (5)
C22—C21—C20	120.26 (17)	O5—V1—O3	162.32 (5)
C22—C21—H21	119.9	O2—V1—O3	89.94 (5)
C20—C21—H21	119.9	O3—V1—O3	0.00 (12)
C21—C22—C23	119.92 (17)	O1—V1—O6	177.74 (6)
C21—C22—H22	120	O4—V1—O6	80.77 (5)
C23—C22—H22	120	O5—V1—O6	81.56 (5)
C24—C23—C22	120.10 (17)	O2—V1—O6	78.71 (5)
C24—C23—H23	120	O3—V1—O6	80.89 (5)
C22—C23—H23	120	O3—V1—O6	80.89 (5)
C23—C24—C19	120.27 (17)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O6—H6A···O7	0.82 (3)	1.83 (3)	2.644 (2)	169 (3)
O7—H7A···O8ⁱ	0.87 (3)	1.90 (3)	2.749 (2)	168 (3)
O8—H8A···O3	0.90 (3)	1.96 (3)	2.853 (2)	178 (3)
C13—H13···O1ⁱⁱ	0.95	2.58	3.487 (2)	160
C32—H32B···O1ⁱ	0.98 (3)	2.43 (3)	3.360 (3)	159 (2)

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

Experimental details

Crystal data
Chemical formula	[V(C₁₅H₁₁O₂)₂O(CH₄O)]·2CH₄O
M_r	609.54
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	100
a, b, c (Å)	16.1411 (1), 10.7450 (6), 18.5378 (13)
β (°)	113.579 (2)
V (Å³)	2946.7 (3)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.39
Crystal size (mm)	0.47 × 0.07 × 0.05

Data collection
Diffractometer	Bruker APEXII KappaCCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2008)
T_min, T_max	0.968, 0.981
No. of measured, independent and observed [I > 2σ(I)] reflections	38614, 7317, 5545
R_int	0.046
(sin θ/λ)_max (Å⁻¹)	0.667

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.041, 0.102, 1.03
No. of reflections	7317
No. of parameters	412
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.45, −0.43

Computer programs: APEX2 (Bruker, 2011), SAINT-Plus (Bruker, 2008), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), Mercury (Macrae et al., 2008), WinGX (Farrugia, 1999), publCIF (Westrip, 2010), PARST (Nardelli, 1995) and PLATON (Spek, 2009).

Selected bond lengths (Å) top

O1—V1	1.5965 (13)	O4—V1	1.9847 (12)
O2—V1	1.9972 (12)	O5—V1	1.9935 (12)
O3—V1	2.0045 (12)	O6—V1	2.3020 (15)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O6—H6A···O7	0.82 (3)	1.83 (3)	2.644 (2)	169 (3)
O7—H7A···O8ⁱ	0.87 (3)	1.90 (3)	2.749 (2)	168 (3)
O8—H8A···O3	0.90 (3)	1.96 (3)	2.853 (2)	178 (3)
C13—H13···O1ⁱⁱ	0.95	2.58	3.487 (2)	159.9
C32—H32B···O1ⁱ	0.98 (3)	2.43 (3)	3.360 (3)	159 (2)

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

Acknowledgements

Financial assistance from the University of the Free State Strategic Academic Cluster Initiative (Materials and Nanosciences), SASOL and the South African National Research Foundation (SA-NRF/THRIP) is gratefully acknowledged.

References

Bansse, W., Ludwig, E., Uhlemann, E., Weller, F., Dehnicke, K. & Herrmann, W. (1992). Z. Anorg. Allg. Chem. 613, 36–44. CSD CrossRef CAS Web of Science Google Scholar
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Bruker (2011). APEX2. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Chen, C. T., Lin, J. S., Kuo, J. H., Weng, S. S., Cuo, T. S., Lin, Y. W., Cheng, C. C., Huang, Y. C., Yu, J. K. & Chou, P. T. (2004). Org. Lett. 6, 4471–4474. Web of Science CSD CrossRef PubMed CAS Google Scholar
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Volume 68| Part 12| December 2012| Pages m1442-m1443

doi:10.1107/S1600536812044686

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metal-organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

trans-Bis(1,3-di­phenyl­propane-1,3-dionato)(methanol)oxidovanadium(IV) methanol disolvate

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

metal-organic compounds

trans-Bis(1,3-diphenylpropane-1,3-dionato)(methanol)oxidovanadium(IV) methanol disolvate