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

In the title compound, [Mg(C₁₂H₉O₂)₂(H₂O)₂], the magnesium cation (site symmetry ) 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.

Key indicators

• Single-crystal X-ray study
• T = 291 K
• Mean [sigma](C-C)= 0.003 Å
• R factor = 0.052
• wR factor = 0.115
• Data-to-parameter ratio = 13.6

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S1. Comment

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

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

S2. Experimental

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.

S3. Refinement

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

Computing details

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

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)

Crystal data

[Mg(C12H9O2)2(H2O)2]	F(000) = 904
Mr = 430.73	Dx = 1.450 Mg m^−3
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 548 reflections
a = 33.261 (19) Å	θ = 2.1–20.2°
b = 7.951 (5) Å	µ = 0.13 mm^−1
c = 7.461 (5) Å	T = 291 K
V = 1973 (2) Å^3	Block, colourless
Z = 4	0.30 × 0.22 × 0.20 mm

Data collection

Bruker Smart Apex CCD diffractometer	1940 independent reflections
Radiation source: sealed tube	1486 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.055
ω scans	θmax = 26.0°, θmin = 2.5°
Absorption correction: multi-scan (SADABS; Bruker, 2000)	h = −40→40
Tmin = 0.97, Tmax = 0.98	k = −8→9
9925 measured reflections	l = −8→9

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)] = 0.052	Hydrogen site location: difmap and geom
wR(F^2) = 0.115	H-atom parameters constrained
S = 1.06	w = 1/[σ^2(Fo^2) + (0.05P)^2 + 0.55P] where P = (Fo^2 + 2Fc^2)/3
1940 reflections	(Δ/σ)max < 0.001
143 parameters	Δρmax = 0.18 e Å^−3
0 restraints	Δρmin = −0.18 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
C1	0.08501 (6)	0.0828 (3)	−0.0880 (3)	0.0288 (5)
C2	0.11300 (7)	0.2069 (3)	−0.1541 (3)	0.0353 (5)
H2	0.1033	0.2962	−0.2219	0.042*
C3	0.15261 (7)	0.1974 (3)	−0.1209 (3)	0.0390 (6)
H3	0.1694	0.2797	−0.1680	0.047*
C4	0.16966 (7)	0.0680 (3)	−0.0178 (3)	0.0349 (5)
C5	0.21048 (7)	0.0694 (3)	0.0294 (3)	0.0440 (6)
H5	0.2270	0.1553	−0.0124	0.053*
C6	0.22596 (8)	−0.0506 (4)	0.1333 (4)	0.0515 (7)
H6	0.2532	−0.0510	0.1612	0.062*
C7	0.20078 (8)	−0.1747 (3)	0.1989 (3)	0.0446 (6)
H7	0.2114	−0.2557	0.2753	0.054*
C8	0.16091 (7)	−0.1827 (3)	0.1556 (3)	0.0397 (6)
H8	0.1452	−0.2693	0.2013	0.048*
C9	0.14354 (6)	−0.0621 (3)	0.0433 (3)	0.0305 (5)
C10	0.10135 (7)	−0.0597 (3)	−0.0013 (3)	0.0310 (5)
C11	0.07582 (7)	−0.2100 (2)	0.0240 (3)	0.0274 (5)
C12	0.09151 (8)	−0.3890 (3)	0.0021 (3)	0.0398 (6)
H12A	0.0898	−0.4469	0.1147	0.060*
H12B	0.1190	−0.3857	−0.0366	0.060*
H12C	0.0756	−0.4470	−0.0857	0.060*
Mg1	0.0000	0.0000	0.0000	0.0322 (3)
O1	0.04736 (4)	0.10416 (19)	−0.1205 (2)	0.0332 (4)
O2	0.03866 (4)	−0.19729 (18)	0.0438 (2)	0.0362 (4)
O3	0.01541 (5)	0.1075 (2)	0.2367 (2)	0.0424 (4)
H3A	−0.0085	0.1493	0.2911	0.051*
H3B	0.0338	0.2002	0.2188	0.051*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0347 (12)	0.0239 (11)	0.0277 (11)	−0.0001 (9)	0.0053 (9)	−0.0074 (9)
C2	0.0465 (14)	0.0251 (11)	0.0344 (12)	−0.0073 (10)	0.0049 (10)	0.0058 (9)
C3	0.0452 (13)	0.0337 (13)	0.0381 (13)	−0.0123 (10)	0.0075 (11)	0.0001 (10)
C4	0.0415 (14)	0.0367 (12)	0.0266 (12)	−0.0006 (10)	0.0055 (9)	−0.0063 (10)
C5	0.0318 (13)	0.0524 (15)	0.0478 (16)	−0.0090 (11)	0.0031 (11)	−0.0110 (13)
C6	0.0376 (14)	0.0677 (19)	0.0492 (16)	0.0067 (13)	−0.0056 (12)	−0.0071 (14)
C7	0.0464 (15)	0.0465 (14)	0.0409 (14)	0.0144 (12)	−0.0089 (11)	0.0019 (12)
C8	0.0377 (13)	0.0457 (14)	0.0356 (13)	0.0073 (11)	−0.0006 (10)	0.0071 (11)
C9	0.0333 (12)	0.0360 (12)	0.0223 (11)	0.0037 (9)	0.0018 (8)	−0.0011 (9)
C10	0.0376 (12)	0.0294 (11)	0.0261 (11)	0.0055 (9)	0.0092 (9)	0.0014 (9)
C11	0.0391 (12)	0.0222 (11)	0.0209 (11)	0.0051 (9)	0.0030 (8)	−0.0020 (8)
C12	0.0532 (15)	0.0199 (11)	0.0462 (14)	0.0007 (10)	0.0033 (12)	0.0018 (10)
Mg1	0.0347 (6)	0.0268 (5)	0.0351 (6)	−0.0003 (4)	−0.0014 (4)	0.0002 (5)
O1	0.0309 (8)	0.0266 (8)	0.0422 (9)	0.0022 (6)	0.0003 (7)	0.0081 (7)
O2	0.0338 (9)	0.0279 (9)	0.0469 (10)	0.0027 (6)	0.0026 (7)	0.0030 (7)
O3	0.0429 (10)	0.0408 (9)	0.0435 (10)	−0.0023 (7)	0.0074 (8)	−0.0149 (8)

Geometric parameters (Å, º)

C1—O1	1.287 (3)	C8—H8	0.9300
C1—C10	1.414 (3)	C9—C10	1.442 (3)
C1—C2	1.443 (3)	C10—C11	1.478 (3)
C2—C3	1.343 (3)	C11—O2	1.249 (3)
C2—H2	0.9300	C11—C12	1.525 (3)
C3—C4	1.404 (3)	C12—H12A	0.9600
C3—H3	0.9300	C12—H12B	0.9600
C4—C5	1.403 (3)	C12—H12C	0.9600
C4—C9	1.425 (3)	Mg1—O1	1.9940 (16)
C5—C6	1.333 (4)	Mg1—O1^i	1.9940 (16)
C5—H5	0.9300	Mg1—O3^i	2.0283 (19)
C6—C7	1.384 (4)	Mg1—O3	2.0283 (19)
C6—H6	0.9300	Mg1—O2^i	2.0545 (17)
C7—C8	1.366 (3)	Mg1—O2	2.0545 (17)
C7—H7	0.9300	O3—H3A	0.9522
C8—C9	1.398 (3)	O3—H3B	0.9661
O1—C1—C10	124.47 (19)	O2—C11—C10	121.23 (18)
O1—C1—C2	118.3 (2)	O2—C11—C12	115.27 (19)
C10—C1—C2	117.1 (2)	C10—C11—C12	122.96 (19)
C3—C2—C1	122.1 (2)	C11—C12—H12A	109.5
C3—C2—H2	119.0	C11—C12—H12B	109.5
C1—C2—H2	119.0	H12A—C12—H12B	109.5
C2—C3—C4	122.6 (2)	C11—C12—H12C	109.5
C2—C3—H3	118.7	H12A—C12—H12C	109.5
C4—C3—H3	118.7	H12B—C12—H12C	109.5
C5—C4—C3	121.5 (2)	O1—Mg1—O1^i	180.0
C5—C4—C9	121.1 (2)	O1—Mg1—O3^i	88.96 (7)
C3—C4—C9	117.4 (2)	O1^i—Mg1—O3^i	91.04 (7)
C6—C5—C4	120.9 (2)	O1—Mg1—O3	91.04 (7)
C6—C5—H5	119.5	O1^i—Mg1—O3	88.96 (7)
C4—C5—H5	119.5	O3^i—Mg1—O3	180.0
C5—C6—C7	118.8 (2)	O1—Mg1—O2^i	96.05 (7)
C5—C6—H6	120.6	O1^i—Mg1—O2^i	83.95 (7)
C7—C6—H6	120.6	O3^i—Mg1—O2^i	91.44 (7)
C8—C7—C6	122.5 (2)	O3—Mg1—O2^i	88.56 (7)
C8—C7—H7	118.8	O1—Mg1—O2	83.95 (7)
C6—C7—H7	118.8	O1^i—Mg1—O2	96.05 (7)
C7—C8—C9	120.7 (2)	O3^i—Mg1—O2	88.56 (7)
C7—C8—H8	119.6	O3—Mg1—O2	91.44 (7)
C9—C8—H8	119.6	O2^i—Mg1—O2	180.0
C8—C9—C4	115.9 (2)	C1—O1—Mg1	128.98 (14)
C8—C9—C10	123.3 (2)	C11—O2—Mg1	131.47 (14)
C4—C9—C10	120.7 (2)	Mg1—O3—H3A	107.9
C1—C10—C9	119.3 (2)	Mg1—O3—H3B	111.1
C1—C10—C11	119.1 (2)	H3A—O3—H3B	108.7
C9—C10—C11	121.27 (19)

Symmetry code: (i) −x, −y, −z.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3A···O2^ii	0.95	2.00	2.885 (2)	153
O3—H3B···O1^iii	0.97	2.02	2.742 (3)	130

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