catena-Poly[[(2-methyl­benzoato-κ2O,O′)sodium]-di-μ-aqua-κ4O:O′]

Danish, M.; Saleem, I.; Ahmad, N.; Raza, A.R.; Starosta, W.; Leciejewicz, J.

doi:10.1107/S1600536810010536

metal-organic compounds

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ISSN: 2056-9890

Volume 66| Part 4| April 2010| Pages m459-m460

doi:10.1107/S1600536810010536

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catena-Poly[[(2-methylbenzoato-κ²O,O′)sodium]-di-μ-aqua-κ⁴O:O′]

Muhammad Danish,^a ^* Iram Saleem,^a Nazir Ahmad,^a Abdul Rauf Raza,^a Wojciech Starosta ^b and Janusz Leciejewicz ^b

^aDepartment of Chemistry, University of Sargodha, Sargodha 40100, Pakistan, and ^bInstitute of Nuclear Chemistry and Technology, ul. Dorodna 16, 03-195 Warszawa, Poland
^*Correspondence e-mail: drdanish62@gmail.com

(Received 11 March 2010; accepted 21 March 2010; online 27 March 2010)

In the title coordination polymer, [Na(C₈H₇O₂)(H₂O)₂]_n, the cation is chelated by the carboxylate O atoms of the anion in a bidentate mode and is surrounded by the O atoms of four water molecules. The coordination of the Na⁺ cation is distorted octahedral. The water molecules bridge adjacent metal cations, forming polymeric layers parallel to (100). The structure is stabilized by an extensive network of O—H⋯O hydrogen bonds.

Related literature

Tin complexes with organic ligands have been studied intensively due to their biological activity, see, for example: Shahzadi et al. (2007 ). For 2-methylbenzoic and 4-methylbenzoic acids as potent allergic sensitizers when applied to human skin, see: Emmet & Suskind (1973 ), and as inhibitors of lettuce fruit germination, see: Reynolds (1978 ). Sodium 2-methylbenzoate has been studied as a precursor in the synthesis of biologically active tin(IV) complexes. For the structure of a sodium complex with a 2-methyl-3,5-dinitrobenzoate ligand, see: Danish et al. (2010 ).

Experimental

Crystal data

[Na(C₈H₇O₂)(H₂O)₂]
M_r = 194.16
Monoclinic, P 2₁ /c
a = 16.145 (3) Å
b = 8.1155 (16) Å
c = 7.3986 (15) Å
β = 92.98 (3)°
V = 968.1 (3) Å³
Z = 4
Mo Kα radiation
μ = 0.14 mm⁻¹
T = 293 K
0.55 × 0.41 × 0.11 mm

Data collection

Kuma KM-4 four-circle diffractometer
Absorption correction: analytical (CrysAlis RED; Oxford Diffraction, 2008 $[Oxford Diffraction (2008). CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England]$ ) T_min = 0.952, T_max = 0.991
3057 measured reflections
2845 independent reflections
1919 reflections with I > 2σ(I)
R_int = 0.024
3 standard reflections every 200 reflections intensity decay: 0.8%

Refinement

R[F² > 2σ(F²)] = 0.043
wR(F²) = 0.141
S = 1.02
2845 reflections
151 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.44 e Å⁻³
Δρ_min = −0.21 e Å⁻³

Table 1
Selected bond lengths (Å)

Na1—O4	2.3599 (13)
Na1—O4ⁱ	2.3689 (13)
Na1—O1	2.4141 (13)
Na1—O3	2.4245 (13)
Na1—O3ⁱⁱ	2.5086 (13)
Na1—O2	2.5387 (14)
Symmetry codes: (i) $[x, -y+{\script{3\over 2}}, z-{\script{1\over 2}}]$ ; (ii) $[-x, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O4—H42⋯O1ⁱⁱⁱ	0.84 (3)	1.94 (3)	2.7582 (17)	163 (2)
O4—H41⋯O2^iv	0.76 (3)	2.03 (3)	2.7874 (17)	171 (2)
O3—H31⋯O1^v	0.88 (3)	1.97 (3)	2.7716 (16)	151 (2)
O3—H32⋯O2ⁱ	0.77 (3)	2.10 (3)	2.8265 (16)	158 (2)
Symmetry codes: (i) $[x, -y+{\script{3\over 2}}, z-{\script{1\over 2}}]$ ; (iii) $[-x, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (iv) -x, -y+1, -z+1; (v) $[x, -y+{\script{3\over 2}}, z+{\script{1\over 2}}]$ .

Data collection: KM-4 Software (Kuma, 1996 $[Kuma (1996). KM-4 Software. Kuma Diffraction Ltd, Wrocław, Poland.]$ ); cell refinement: KM-4 Software; data reduction: DATAPROC (Kuma, 2001 $[Kuma (2001). DATAPROC. Kuma Diffraction Ltd, Wrocław, Poland.]$ ); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810010536/wm2315sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536810010536/wm2315Isup2.hkl

checkCIF report

Comment top

2-methylbenzoic and 4-methylbenzoic acids were studied as potent allergic sensitizers when applied to human skin (Emmet & Suskind, 1973). They are also used for the inhibition of lettuce fruit germination (Reynolds, 1978). The title compound was isolated as an intermediate during synthesis of biologically active organotin carboxylates (Shahzadi et al., 2007).

In the polymeric structure of the title compound, [Na(C₈H₇O₂)(H₂O)₂]_n, each sodium ion is coordinated by the carboxylic O atoms of the bidentate anion and by four bridging water O atoms (Fig.1). The coordination geometry around the Na⁺ cation is distorted octahedral with the equatorial plane composed of the carboxylate atoms O1 and O2 and the symmetry-related water O4 and O4ⁱ atoms [r.m.s. is 0.0580 (2) Å]. Water O3 and O3ⁱⁱ atoms are at the apical positions. The resulting coordination differs from the one reported in the structure of the Na⁺ complex with the 2-methyl-3,5-dinitrobenzoate anion. Here the metal exhibits coordination number 7 (Danish et al., 2010). The 2-methylbenzoate ring in the title compound is planar with a r.m.s. of 0.0089 (2) Å; the carboxylic group C17/O1/O2 makes an dihedral angle of 37.1 (2)° with the aromatic ring. Na⁺ cations form sheets parallel to the (100) plane in which they are grouped into pairs (Fig. 2). In such a pair, Na⁺ cations are coordinated by ligands with their 2-methylbenzoate rings pointing in the same direction but twisted by an angle of 73.0 (2)° relative to each other. Water O atoms bridge in two directions: via O4 atoms along the b axis and via O3 atoms along the c axis. Water molecules act as donors and carboxylate O atoms as acceptors in a network of O—H··· O hydrogen bonds that consolidate the crystal structure. Geometrical parameters of the hydrogen bonding are listed in Table 2.

Related literature top

Tin complexes with organic ligands have been studied intensively due to their biological activity, see, for example: Shahzadi et al. (2007). For 2-methylbenzoic and 4-methylbenzoic acids as potent allergic sensitizers when applied to human skin, see: Emmet & Suskind (1973), and as inhibitors of lettuce fruit germination, see: Reynolds (1978). Sodium 2-methylbenzoate has been studied as a precursor in the synthesis of biologically active tin(IV) complexes. For the structure of a sodium complex with a 2-methyl-3,5-dinitrobenzoate ligand, see: Danish et al. (2010).

Experimental top

50 ml of an aqueous solution containing 0.0147 mmol of 2-methylbenzoic acid were added dropwise with continuous stirring at room trmperature to 50 ml of an aqueous solution of sodium bicarbonate (0.0147 mmol). The mixture was then refluxed for 3 hours, cooled to room temperature and concentrated under reduced pressure to afford a dry solid mass which was then purified by re-crystallization from a distilled water-ethanol (4:1) mixture to obtain single crystals.

Computing details top

Data collection: KM-4 Software (Kuma, 1996); cell refinement: KM-4 Software (Kuma, 1996); data reduction: DATAPROC (Kuma, 2001); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. A structural unit of (1) with atom labelling scheme and 50% probability displacement ellipsoids. Symmetry code: (I) x,-y+3/2,z-1;2; (II) -x,y-1/2,-z+1/2.
	Fig. 2. Packing diagram of the structure.

catena-Poly[[(2-methylbenzoato-κ²O,O')sodium]- di-µ-aqua-κ⁴O:O'] top

Crystal data top

[Na(C₈H₇O₂)(H₂O)₂]	F(000) = 408
M_r = 194.16	D_x = 1.332 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 25 reflections
a = 16.145 (3) Å	θ = 6–15°
b = 8.1155 (16) Å	µ = 0.14 mm⁻¹
c = 7.3986 (15) Å	T = 293 K
β = 92.98 (3)°	Block, colourless
V = 968.1 (3) Å³	0.55 × 0.41 × 0.11 mm
Z = 4

Data collection top

Kuma KM-4 four-circle diffractometer	1919 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.024
Graphite monochromator	θ_max = 30.1°, θ_min = 1.3°
profile data from ω/2θ scans	h = −22→22
Absorption correction: analytical (CrysAlis RED; Oxford Diffraction, 2008)	k = 0→11
T_min = 0.952, T_max = 0.991	l = −10→0
3057 measured reflections	3 standard reflections every 200 reflections
2845 independent reflections	intensity decay: 0.8%

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)] = 0.043	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.141	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	w = 1/[σ²(F_o²) + (0.0889P)² + 0.1369P] where P = (F_o² + 2F_c²)/3
2845 reflections	(Δ/σ)_max < 0.001
151 parameters	Δρ_max = 0.44 e Å⁻³
0 restraints	Δρ_min = −0.21 e Å⁻³

Crystal data top

[Na(C₈H₇O₂)(H₂O)₂]	V = 968.1 (3) Å³
M_r = 194.16	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 16.145 (3) Å	µ = 0.14 mm⁻¹
b = 8.1155 (16) Å	T = 293 K
c = 7.3986 (15) Å	0.55 × 0.41 × 0.11 mm
β = 92.98 (3)°

Data collection top

Kuma KM-4 four-circle diffractometer	1919 reflections with I > 2σ(I)
Absorption correction: analytical (CrysAlis RED; Oxford Diffraction, 2008)	R_int = 0.024
T_min = 0.952, T_max = 0.991	3 standard reflections every 200 reflections
3057 measured reflections	intensity decay: 0.8%
2845 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.043	0 restraints
wR(F²) = 0.141	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	Δρ_max = 0.44 e Å⁻³
2845 reflections	Δρ_min = −0.21 e Å⁻³
151 parameters

Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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

	x	y	z	U_iso*/U_eq
Na1	0.01791 (3)	0.64831 (7)	0.25611 (7)	0.03320 (17)
O2	0.14852 (7)	0.53347 (14)	0.41532 (13)	0.0386 (2)
C7	0.18004 (8)	0.53264 (15)	0.26404 (16)	0.0273 (2)
C1	0.27247 (8)	0.53757 (16)	0.25234 (17)	0.0305 (3)
C2	0.32656 (10)	0.4527 (2)	0.3718 (2)	0.0425 (3)
C6	0.30354 (11)	0.6271 (3)	0.1107 (2)	0.0492 (4)
C3	0.41092 (11)	0.4583 (3)	0.3414 (3)	0.0562 (5)
C8	0.29779 (16)	0.3518 (4)	0.5275 (4)	0.0852 (9)
H8A	0.2774	0.4239	0.6181	0.128*
H8B	0.3434	0.2884	0.5788	0.128*
H8C	0.2542	0.2789	0.4848	0.128*
C5	0.38805 (13)	0.6352 (3)	0.0885 (4)	0.0694 (6)
C4	0.44096 (12)	0.5494 (3)	0.2038 (4)	0.0672 (6)
O1	0.13648 (6)	0.53062 (13)	0.11780 (13)	0.0367 (2)
O3	0.08470 (7)	0.91596 (13)	0.25956 (15)	0.0365 (2)
O4	−0.05771 (7)	0.74541 (15)	0.49901 (14)	0.0357 (2)
H32	0.1128 (15)	0.918 (3)	0.179 (4)	0.055 (6)*
H31	0.1175 (16)	0.921 (3)	0.357 (4)	0.069 (7)*
H41	−0.0863 (15)	0.676 (3)	0.526 (3)	0.057 (7)*
H42	−0.0901 (14)	0.819 (3)	0.458 (3)	0.056 (6)*
H5	0.2640 (13)	0.693 (3)	0.026 (3)	0.056 (6)*
H2	0.4464 (15)	0.395 (3)	0.412 (3)	0.060 (6)*
H4	0.4058 (17)	0.705 (4)	−0.018 (4)	0.092 (9)*
H3	0.495 (2)	0.556 (4)	0.179 (4)	0.096 (9)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Na1	0.0366 (3)	0.0334 (3)	0.0296 (3)	0.0032 (2)	0.0015 (2)	0.0004 (2)
O2	0.0421 (5)	0.0471 (6)	0.0270 (4)	−0.0009 (4)	0.0063 (4)	0.0023 (4)
C7	0.0323 (6)	0.0244 (5)	0.0251 (5)	−0.0006 (4)	0.0012 (4)	0.0000 (4)
C1	0.0319 (6)	0.0309 (6)	0.0286 (6)	−0.0002 (5)	0.0002 (5)	−0.0024 (5)
C2	0.0395 (7)	0.0431 (8)	0.0439 (8)	0.0023 (6)	−0.0073 (6)	0.0027 (6)
C6	0.0441 (8)	0.0588 (10)	0.0452 (9)	−0.0034 (7)	0.0089 (7)	0.0115 (7)
C3	0.0379 (8)	0.0628 (12)	0.0664 (12)	0.0075 (7)	−0.0114 (8)	−0.0096 (9)
C8	0.0650 (13)	0.106 (2)	0.0834 (16)	0.0098 (13)	−0.0112 (12)	0.0597 (15)
C5	0.0497 (11)	0.0876 (16)	0.0730 (14)	−0.0130 (10)	0.0234 (10)	0.0141 (12)
C4	0.0341 (8)	0.0854 (16)	0.0830 (15)	−0.0045 (9)	0.0118 (9)	−0.0171 (12)
O1	0.0374 (5)	0.0440 (6)	0.0279 (5)	0.0005 (4)	−0.0045 (4)	−0.0024 (4)
O3	0.0474 (6)	0.0369 (5)	0.0253 (5)	−0.0008 (4)	0.0018 (4)	0.0001 (4)
O4	0.0415 (5)	0.0336 (5)	0.0320 (5)	−0.0002 (5)	0.0009 (4)	−0.0016 (4)

Geometric parameters (Å, º) top

Na1—O4	2.3599 (13)	C2—C8	1.506 (3)
Na1—O4ⁱ	2.3689 (13)	C6—C5	1.384 (3)
Na1—O1	2.4141 (13)	C6—H5	1.02 (2)
Na1—O3	2.4245 (13)	C3—C4	1.367 (4)
Na1—O3ⁱⁱ	2.5086 (13)	C3—H2	0.91 (3)
Na1—O2	2.5387 (14)	C8—H8A	0.9600
Na1—C7	2.7787 (14)	C8—H8B	0.9600
Na1—Na1ⁱ	4.0508 (8)	C8—H8C	0.9600
Na1—Na1ⁱⁱⁱ	4.0508 (8)	C5—C4	1.366 (4)
Na1—Na1ⁱⁱ	4.0990 (8)	C5—H4	1.02 (3)
Na1—Na1^iv	4.0991 (8)	C4—H3	0.90 (3)
O2—C7	1.2534 (16)	O3—Na1^iv	2.5087 (13)
C7—O1	1.2596 (16)	O3—H32	0.77 (3)
C7—C1	1.4999 (18)	O3—H31	0.88 (3)
C1—C6	1.390 (2)	O4—Na1ⁱⁱⁱ	2.3689 (13)
C1—C2	1.392 (2)	O4—H41	0.76 (3)
C2—C3	1.393 (3)	O4—H42	0.84 (3)

O4—Na1—O4ⁱ	102.97 (4)	O2—Na1—Na1^iv	119.11 (3)
O4—Na1—O1	155.22 (5)	C7—Na1—Na1^iv	117.81 (3)
O4ⁱ—Na1—O1	100.99 (4)	Na1ⁱ—Na1—Na1^iv	65.37 (2)
O4—Na1—O3	86.57 (5)	Na1ⁱⁱⁱ—Na1—Na1^iv	67.05 (2)
O4ⁱ—Na1—O3	83.84 (5)	Na1ⁱⁱ—Na1—Na1^iv	163.72 (3)
O1—Na1—O3	89.82 (4)	C7—O2—Na1	87.34 (8)
O4—Na1—O3ⁱⁱ	85.39 (5)	O2—C7—O1	122.18 (12)
O4ⁱ—Na1—O3ⁱⁱ	85.70 (5)	O2—C7—C1	120.18 (11)
O1—Na1—O3ⁱⁱ	102.67 (4)	O1—C7—C1	117.62 (12)
O3—Na1—O3ⁱⁱ	165.05 (4)	O2—C7—Na1	65.88 (8)
O4—Na1—O2	102.67 (5)	O1—C7—Na1	60.19 (7)
O4ⁱ—Na1—O2	152.54 (4)	C1—C7—Na1	158.26 (9)
O1—Na1—O2	52.67 (4)	C6—C1—C2	119.88 (15)
O3—Na1—O2	88.04 (4)	C6—C1—C7	117.16 (13)
O3ⁱⁱ—Na1—O2	106.03 (4)	C2—C1—C7	122.92 (13)
O4—Na1—C7	128.38 (5)	C1—C2—C3	117.90 (16)
O4ⁱ—Na1—C7	125.85 (5)	C1—C2—C8	123.11 (16)
O1—Na1—C7	26.92 (4)	C3—C2—C8	118.97 (17)
O3—Na1—C7	83.36 (4)	C5—C6—C1	120.70 (18)
O3ⁱⁱ—Na1—C7	111.48 (4)	C5—C6—H5	119.4 (12)
O2—Na1—C7	26.78 (3)	C1—C6—H5	119.8 (12)
O4—Na1—Na1ⁱ	125.73 (4)	C4—C3—C2	121.71 (18)
O4ⁱ—Na1—Na1ⁱ	30.99 (3)	C4—C3—H2	119.7 (15)
O1—Na1—Na1ⁱ	74.72 (3)	C2—C3—H2	118.5 (15)
O3—Na1—Na1ⁱ	67.88 (3)	C2—C8—H8A	109.5
O3ⁱⁱ—Na1—Na1ⁱ	107.18 (3)	C2—C8—H8B	109.5
O2—Na1—Na1ⁱ	122.27 (3)	H8A—C8—H8B	109.5
C7—Na1—Na1ⁱ	96.45 (4)	C2—C8—H8C	109.5
O4—Na1—Na1ⁱⁱⁱ	31.13 (3)	H8A—C8—H8C	109.5
O4ⁱ—Na1—Na1ⁱⁱⁱ	124.09 (4)	H8B—C8—H8C	109.5
O1—Na1—Na1ⁱⁱⁱ	125.87 (3)	C4—C5—C6	119.3 (2)
O3—Na1—Na1ⁱⁱⁱ	69.30 (4)	C4—C5—H4	124.9 (16)
O3ⁱⁱ—Na1—Na1ⁱⁱⁱ	108.49 (3)	C6—C5—H4	115.8 (16)
O2—Na1—Na1ⁱⁱⁱ	76.42 (3)	C5—C4—C3	120.39 (17)
C7—Na1—Na1ⁱⁱⁱ	99.38 (4)	C5—C4—H3	115 (2)
Na1ⁱ—Na1—Na1ⁱⁱⁱ	131.91 (3)	C3—C4—H3	125 (2)
O4—Na1—Na1ⁱⁱ	105.63 (4)	C7—O1—Na1	92.89 (8)
O4ⁱ—Na1—Na1ⁱⁱ	106.05 (4)	Na1—O3—Na1^iv	112.37 (5)
O1—Na1—Na1ⁱⁱ	73.32 (3)	Na1—O3—H32	107.0 (18)
O3—Na1—Na1ⁱⁱ	161.66 (4)	Na1^iv—O3—H32	111.3 (18)
O3ⁱⁱ—Na1—Na1ⁱⁱ	33.16 (3)	Na1—O3—H31	107.4 (17)
O2—Na1—Na1ⁱⁱ	76.09 (3)	Na1^iv—O3—H31	111.9 (17)
C7—Na1—Na1ⁱⁱ	78.33 (3)	H32—O3—H31	106 (2)
Na1ⁱ—Na1—Na1ⁱⁱ	112.95 (2)	Na1—O4—Na1ⁱⁱⁱ	117.88 (5)
Na1ⁱⁱⁱ—Na1—Na1ⁱⁱ	114.63 (2)	Na1—O4—H41	107.1 (18)
O4—Na1—Na1^iv	66.94 (3)	Na1ⁱⁱⁱ—O4—H41	110.8 (17)
O4ⁱ—Na1—Na1^iv	63.62 (3)	Na1—O4—H42	107.3 (15)
O1—Na1—Na1^iv	119.76 (4)	Na1ⁱⁱⁱ—O4—H42	108.5 (16)
O3—Na1—Na1^iv	34.47 (3)	H41—O4—H42	104 (2)
O3ⁱⁱ—Na1—Na1^iv	130.62 (4)

Symmetry codes: (i) x, −y+3/2, z−1/2; (ii) −x, y−1/2, −z+1/2; (iii) x, −y+3/2, z+1/2; (iv) −x, y+1/2, −z+1/2.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O4—H42···O1^iv	0.84 (3)	1.94 (3)	2.7582 (17)	163 (2)
O4—H41···O2^v	0.76 (3)	2.03 (3)	2.7874 (17)	171 (2)
O3—H31···O1ⁱⁱⁱ	0.88 (3)	1.97 (3)	2.7716 (16)	151 (2)
O3—H32···O2ⁱ	0.77 (3)	2.10 (3)	2.8265 (16)	158 (2)

Symmetry codes: (i) x, −y+3/2, z−1/2; (iii) x, −y+3/2, z+1/2; (iv) −x, y+1/2, −z+1/2; (v) −x, −y+1, −z+1.

Experimental details

Crystal data
Chemical formula	[Na(C₈H₇O₂)(H₂O)₂]
M_r	194.16
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	293
a, b, c (Å)	16.145 (3), 8.1155 (16), 7.3986 (15)
β (°)	92.98 (3)
V (Å³)	968.1 (3)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.14
Crystal size (mm)	0.55 × 0.41 × 0.11

Data collection
Diffractometer	Kuma KM-4 four-circle diffractometer
Absorption correction	Analytical (CrysAlis RED; Oxford Diffraction, 2008)
T_min, T_max	0.952, 0.991
No. of measured, independent and observed [I > 2σ(I)] reflections	3057, 2845, 1919
R_int	0.024
(sin θ/λ)_max (Å⁻¹)	0.705

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.043, 0.141, 1.02
No. of reflections	2845
No. of parameters	151
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.44, −0.21

Computer programs: KM-4 Software (Kuma, 1996), DATAPROC (Kuma, 2001), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Selected bond lengths (Å) top

Na1—O4	2.3599 (13)	Na1—O3	2.4245 (13)
Na1—O4ⁱ	2.3689 (13)	Na1—O3ⁱⁱ	2.5086 (13)
Na1—O1	2.4141 (13)	Na1—O2	2.5387 (14)

Symmetry codes: (i) x, −y+3/2, z−1/2; (ii) −x, y−1/2, −z+1/2.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O4—H42···O1ⁱⁱⁱ	0.84 (3)	1.94 (3)	2.7582 (17)	163 (2)
O4—H41···O2^iv	0.76 (3)	2.03 (3)	2.7874 (17)	171 (2)
O3—H31···O1^v	0.88 (3)	1.97 (3)	2.7716 (16)	151 (2)
O3—H32···O2ⁱ	0.77 (3)	2.10 (3)	2.8265 (16)	158 (2)

Symmetry codes: (i) x, −y+3/2, z−1/2; (iii) −x, y+1/2, −z+1/2; (iv) −x, −y+1, −z+1; (v) x, −y+3/2, z+1/2.

Acknowledgements

MD acknowledges the Australian Government for the award of an Endeavour Post Doctoral Fellowship for the year 2009–2010.

References

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