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Acta Cryst. (2007). E63, m1665    [ doi:10.1107/S1600536807023677 ]

Bis(1-acetyl-2-naphtholato)diaquamagnesium(II)

L.-H. Wang, J. Yin and X.-S. Tai

Abstract top

In the title compound, [Mg(C12H9O2)2(H2O)2], the magnesium cation (site symmetry \overline{1}) is octahedrally coordinated by two O,O'-bidentate 1-acetyl-2-naphtholate anions and two water molecules. Intermolecular O-H...O hydrogen bonds help to consolidate the crystal packing.

Comment top

The coordination chemistry of Mg(II) ion has received more and more attention over the past two decades (Erxleben et al., 2001). We now report the synthesis and structure of the title compound, (I), (Fig. 1).

In the molecule of (I), The Mg (II) center (site symmetry 1) is six-coordinate (Table 1) with six O-atom donors of 1-acetyl-2-naphthol and H2O. The C11—O2 [1.249 (2) Å] length is close to a double-bond. Otherwise, the geometrical parameters for (I) are normal. Intermolecular O—H···O hydrogen bonds occur and help to consolidate the crystal packing (Table 2).

Related literature top

For background information on magnesium coordination chemistry, see Erxleben et al. (2001).

Experimental top

1 mmol of magnesium perchlorate was added to a solution of 1-acetyl-2-naphthol (2 mmol) in 10 ml of 95% ethanol. The mixture was stirred for 3 h at refluxing temperature. After evaporating some ethanol, clear blocks of (I) were obtained after two weeks.

Refinement top

The water H atoms were located in a difference map and refined as riding with Uiso(H) = 1.2Ueq(O). The C-bound H atoms were placed geometrically (C—H = 0.93–0.96 Å, and refined as riding with Uiso(H) = 1.2Ueq(C) or 1.5Ueq(methyl C).

Computing details top

Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Bruker, 2000); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Figures top
[Figure 1] Fig. 1. The molecular structure of (I) showing 30% displacement ellipsoids (arbitrary spheres for the H atoms). Atoms with the suffix A are generated by the symmetry operation (-x, -y, -z).
bis(1-acetyl-2-naphtholato)diaquamagnesium(II) top
Crystal data top
[Mg(C12H9O2)2(H2O)2]F(000) = 904
Mr = 430.73Dx = 1.450 Mg m−3
Orthorhombic, PbcaMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2abCell parameters from 548 reflections
a = 33.261 (19) Åθ = 2.1–20.2°
b = 7.951 (5) ŵ = 0.13 mm−1
c = 7.461 (5) ÅT = 291 K
V = 1973 (2) Å3Block, colourless
Z = 40.30 × 0.22 × 0.20 mm
Data collection top
Bruker Smart Apex CCD
diffractometer		1940 independent reflections
Radiation source: sealed tube1486 reflections with I > 2σ(I)
graphiteRint = 0.055
ω scansθmax = 26.0°, θmin = 2.5°
Absorption correction: multi-scan
(SADABS; Bruker, 2000)		h = −40→40
Tmin = 0.97, Tmax = 0.98k = −8→9
9925 measured reflectionsl = −8→9
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.052Hydrogen site location: difmap and geom
wR(F2) = 0.115H-atom parameters constrained
S = 1.06 w = 1/[σ2(Fo2) + (0.05P)2 + 0.55P]
where P = (Fo2 + 2Fc2)/3
1940 reflections(Δ/σ)max < 0.001
143 parametersΔρmax = 0.18 e Å−3
0 restraintsΔρmin = −0.18 e Å−3
Crystal data top
[Mg(C12H9O2)2(H2O)2]V = 1973 (2) Å3
Mr = 430.73Z = 4
Orthorhombic, PbcaMo Kα radiation
a = 33.261 (19) ŵ = 0.13 mm−1
b = 7.951 (5) ÅT = 291 K
c = 7.461 (5) Å0.30 × 0.22 × 0.20 mm
Data collection top
Bruker Smart Apex CCD
diffractometer		1940 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2000)		1486 reflections with I > 2σ(I)
Tmin = 0.97, Tmax = 0.98Rint = 0.055
9925 measured reflectionsθmax = 26.0°
Refinement top
R[F2 > 2σ(F2)] = 0.052H-atom parameters constrained
wR(F2) = 0.115Δρmax = 0.18 e Å−3
S = 1.06Δρmin = −0.18 e Å−3
1940 reflectionsAbsolute structure: ?
143 parametersFlack parameter: ?
0 restraintsRogers parameter: ?
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
xyzUiso*/Ueq
C10.08501 (6)0.0828 (3)−0.0880 (3)0.0288 (5)
C20.11300 (7)0.2069 (3)−0.1541 (3)0.0353 (5)
H20.10330.2962−0.22190.042*
C30.15261 (7)0.1974 (3)−0.1209 (3)0.0390 (6)
H30.16940.2797−0.16800.047*
C40.16966 (7)0.0680 (3)−0.0178 (3)0.0349 (5)
C50.21048 (7)0.0694 (3)0.0294 (3)0.0440 (6)
H50.22700.1553−0.01240.053*
C60.22596 (8)−0.0506 (4)0.1333 (4)0.0515 (7)
H60.2532−0.05100.16120.062*
C70.20078 (8)−0.1747 (3)0.1989 (3)0.0446 (6)
H70.2114−0.25570.27530.054*
C80.16091 (7)−0.1827 (3)0.1556 (3)0.0397 (6)
H80.1452−0.26930.20130.048*
C90.14354 (6)−0.0621 (3)0.0433 (3)0.0305 (5)
C100.10135 (7)−0.0597 (3)−0.0013 (3)0.0310 (5)
C110.07582 (7)−0.2100 (2)0.0240 (3)0.0274 (5)
C120.09151 (8)−0.3890 (3)0.0021 (3)0.0398 (6)
H12A0.0898−0.44690.11470.060*
H12B0.1190−0.3857−0.03660.060*
H12C0.0756−0.4470−0.08570.060*
Mg10.00000.00000.00000.0322 (3)
O10.04736 (4)0.10416 (19)−0.1205 (2)0.0332 (4)
O20.03866 (4)−0.19729 (18)0.0438 (2)0.0362 (4)
O30.01541 (5)0.1075 (2)0.2367 (2)0.0424 (4)
H3A−0.00850.14930.29110.051*
H3B0.03380.20020.21880.051*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0347 (12)0.0239 (11)0.0277 (11)−0.0001 (9)0.0053 (9)−0.0074 (9)
C20.0465 (14)0.0251 (11)0.0344 (12)−0.0073 (10)0.0049 (10)0.0058 (9)
C30.0452 (13)0.0337 (13)0.0381 (13)−0.0123 (10)0.0075 (11)0.0001 (10)
C40.0415 (14)0.0367 (12)0.0266 (12)−0.0006 (10)0.0055 (9)−0.0063 (10)
C50.0318 (13)0.0524 (15)0.0478 (16)−0.0090 (11)0.0031 (11)−0.0110 (13)
C60.0376 (14)0.0677 (19)0.0492 (16)0.0067 (13)−0.0056 (12)−0.0071 (14)
C70.0464 (15)0.0465 (14)0.0409 (14)0.0144 (12)−0.0089 (11)0.0019 (12)
C80.0377 (13)0.0457 (14)0.0356 (13)0.0073 (11)−0.0006 (10)0.0071 (11)
C90.0333 (12)0.0360 (12)0.0223 (11)0.0037 (9)0.0018 (8)−0.0011 (9)
C100.0376 (12)0.0294 (11)0.0261 (11)0.0055 (9)0.0092 (9)0.0014 (9)
C110.0391 (12)0.0222 (11)0.0209 (11)0.0051 (9)0.0030 (8)−0.0020 (8)
C120.0532 (15)0.0199 (11)0.0462 (14)0.0007 (10)0.0033 (12)0.0018 (10)
Mg10.0347 (6)0.0268 (5)0.0351 (6)−0.0003 (4)−0.0014 (4)0.0002 (5)
O10.0309 (8)0.0266 (8)0.0422 (9)0.0022 (6)0.0003 (7)0.0081 (7)
O20.0338 (9)0.0279 (9)0.0469 (10)0.0027 (6)0.0026 (7)0.0030 (7)
O30.0429 (10)0.0408 (9)0.0435 (10)−0.0023 (7)0.0074 (8)−0.0149 (8)
Geometric parameters (Å, °) top
C1—O11.287 (3)C8—H80.9300
C1—C101.414 (3)C9—C101.442 (3)
C1—C21.443 (3)C10—C111.478 (3)
C2—C31.343 (3)C11—O21.249 (3)
C2—H20.9300C11—C121.525 (3)
C3—C41.404 (3)C12—H12A0.9600
C3—H30.9300C12—H12B0.9600
C4—C51.403 (3)C12—H12C0.9600
C4—C91.425 (3)Mg1—O11.9940 (16)
C5—C61.333 (4)Mg1—O1i1.9940 (16)
C5—H50.9300Mg1—O3i2.0283 (19)
C6—C71.384 (4)Mg1—O32.0283 (19)
C6—H60.9300Mg1—O2i2.0545 (17)
C7—C81.366 (3)Mg1—O22.0545 (17)
C7—H70.9300O3—H3A0.9522
C8—C91.398 (3)O3—H3B0.9661
O1—C1—C10124.47 (19)O2—C11—C10121.23 (18)
O1—C1—C2118.3 (2)O2—C11—C12115.27 (19)
C10—C1—C2117.1 (2)C10—C11—C12122.96 (19)
C3—C2—C1122.1 (2)C11—C12—H12A109.5
C3—C2—H2119.0C11—C12—H12B109.5
C1—C2—H2119.0H12A—C12—H12B109.5
C2—C3—C4122.6 (2)C11—C12—H12C109.5
C2—C3—H3118.7H12A—C12—H12C109.5
C4—C3—H3118.7H12B—C12—H12C109.5
C5—C4—C3121.5 (2)O1—Mg1—O1i180.0
C5—C4—C9121.1 (2)O1—Mg1—O3i88.96 (7)
C3—C4—C9117.4 (2)O1i—Mg1—O3i91.04 (7)
C6—C5—C4120.9 (2)O1—Mg1—O391.04 (7)
C6—C5—H5119.5O1i—Mg1—O388.96 (7)
C4—C5—H5119.5O3i—Mg1—O3180.0
C5—C6—C7118.8 (2)O1—Mg1—O2i96.05 (7)
C5—C6—H6120.6O1i—Mg1—O2i83.95 (7)
C7—C6—H6120.6O3i—Mg1—O2i91.44 (7)
C8—C7—C6122.5 (2)O3—Mg1—O2i88.56 (7)
C8—C7—H7118.8O1—Mg1—O283.95 (7)
C6—C7—H7118.8O1i—Mg1—O296.05 (7)
C7—C8—C9120.7 (2)O3i—Mg1—O288.56 (7)
C7—C8—H8119.6O3—Mg1—O291.44 (7)
C9—C8—H8119.6O2i—Mg1—O2180.0
C8—C9—C4115.9 (2)C1—O1—Mg1128.98 (14)
C8—C9—C10123.3 (2)C11—O2—Mg1131.47 (14)
C4—C9—C10120.7 (2)Mg1—O3—H3A107.9
C1—C10—C9119.3 (2)Mg1—O3—H3B111.1
C1—C10—C11119.1 (2)H3A—O3—H3B108.7
C9—C10—C11121.27 (19)
Symmetry codes: (i) −x, −y, −z.
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
O3—H3A···O2ii0.952.002.885 (2)153
O3—H3B···O1iii0.972.022.742 (3)130
Symmetry codes: (ii) −x, y+1/2, −z+1/2; (iii) x, −y+1/2, z+1/2.
Table 1
Selected geometric parameters (Å) top
Mg1—O11.9940 (16)Mg1—O22.0545 (17)
Mg1—O3i2.0283 (19)
Symmetry codes: (i) −x, −y, −z.
Table 2
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
O3—H3A···O2ii0.952.002.885 (2)153
O3—H3B···O1iii0.972.022.742 (3)130
Symmetry codes: (ii) −x, y+1/2, −z+1/2; (iii) x, −y+1/2, z+1/2.
Acknowledgements top

The authors would like to thank the National Natural Science Foundation of China (20671073), the NingXia Natural Gas Transfering Key Laboratory (2004007), the Science and Technology Foundation of Weifang and Weifang University for research grants.

references
References top

Bruker (2000). SMART, SAINT, SADABS and SHELXTL. Bruker AXS Inc., Madison, Wisconsin, USA.

Erxleben, A. & Schumacher, D. (2001). Eur. J. Inorg. Chem. Vol.?, 3039–3043.