catena-Poly[[(2-methyl-benzoato-κO,O')sodium]-di-μ-aqua-κO:O'].

In the title coordination polymer, [Na(C(8)H(7)O(2))(H(2)O)(2)](n), the cation is chelated by the carboxyl-ate O atoms of the anion in a bidentate mode and is surrounded by the O atoms of four water mol-ecules. The coordination of the Na(+) cation is distorted octa-hedral. The water mol-ecules 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 = 194.16

Monoclinic,

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 ▶) 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[F 2 > 2σ(F 2)] = 0.043

wR(F 2) = 0.141

S = 1.02

2845 reflections

151 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.44 e Å−3

Δρmin = −0.21 e Å−3

Data collection: KM-4 Software (Kuma, 1996 ▶); cell refinement: KM-4 Software; 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.

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

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

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

[Na(C8H7O2)(H2O)2]	F(000) = 408
Mr = 194.16	Dx = 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

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

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(Fo2) + (0.0889P)2 + 0.1369P] where P = (Fo2 + 2Fc2)/3
2845 reflections	(Δ/σ)max < 0.001
151 parameters	Δρmax = 0.44 e Å−3
0 restraints	Δρmin = −0.21 e Å−3

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.

	x	y	z	Uiso*/Ueq
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)*

	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)

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—Na1iv	4.0991 (8)	C4—H3	0.90 (3)
O2—C7	1.2534 (16)	O3—Na1iv	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—Na1iv	119.11 (3)
O4—Na1—O1	155.22 (5)	C7—Na1—Na1iv	117.81 (3)
O4i—Na1—O1	100.99 (4)	Na1i—Na1—Na1iv	65.37 (2)
O4—Na1—O3	86.57 (5)	Na1iii—Na1—Na1iv	67.05 (2)
O4i—Na1—O3	83.84 (5)	Na1ii—Na1—Na1iv	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—Na1iv	112.37 (5)
O1—Na1—Na1ii	73.32 (3)	Na1—O3—H32	107.0 (18)
O3—Na1—Na1ii	161.66 (4)	Na1iv—O3—H32	111.3 (18)
O3ii—Na1—Na1ii	33.16 (3)	Na1—O3—H31	107.4 (17)
O2—Na1—Na1ii	76.09 (3)	Na1iv—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—Na1iv	66.94 (3)	Na1iii—O4—H41	110.8 (17)
O4i—Na1—Na1iv	63.62 (3)	Na1—O4—H42	107.3 (15)
O1—Na1—Na1iv	119.76 (4)	Na1iii—O4—H42	108.5 (16)
O3—Na1—Na1iv	34.47 (3)	H41—O4—H42	104 (2)
O3ii—Na1—Na1iv	130.62 (4)

D—H···A	D—H	H···A	D···A	D—H···A
O4—H42···O1iv	0.84 (3)	1.94 (3)	2.7582 (17)	163 (2)
O4—H41···O2v	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)

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) ; (ii) .

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⋯O2iv	0.76 (3)	2.03 (3)	2.7874 (17)	171 (2)
O3—H31⋯O1v	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) ; (iii) ; (iv) ; (v) .