Poly[[μ(10)-2,3-bis(carboxymethyl)butanedioato]disodium].

The asymmetric unit of the title compound, [Na(2)(C(8)H(8)O(8))](n), contains one Na(+) ion and half of a 2,3-bis(carboxymethyl)butanedioate (H(2)BTC(2-)) dianion, which lies on a center of symmetry. The dianion exhibits a μ(10)-bridging mode. Each Na atom lies in a NaO(6) octa-hedron defined by six O atoms from five dianions. Adjacent NaO(6) octa-hedra share a common O-O edge, generating a biocta-hedron; adjacent biocta-hedra are O-O edge-connected to one another, building up a chain along [001]. The chains are connected by adjacent H(2)BTC(2-) anions into a three-dimensional framework. The structure is further stabilized by O-H⋯O hydrogen bonds.

Related literature

For related structures, see: Delgado et al. (2007 ▶); Liu et al. (2008 ▶); Wang et al. (2005 ▶); Zheng et al. (2004 ▶); Zhu & Zheng (2010 ▶).

Experimental

Crystal data

[Na2(C8H8O8)]

M = 278.12

Orthorhombic,

a = 8.9053 (18) Å

b = 8.6395 (17) Å

c = 12.527 (3) Å

V = 963.8 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.24 mm−1

T = 293 K

0.44 × 0.36 × 0.32 mm

Data collection

Rigaku R-AXIS RAPID diffractometer

Absorption correction: multi-scan (ABSCOR; Higashi, 1995 ▶) T min = 0.900, T max = 0.925

8610 measured reflections

1097 independent reflections

1000 reflections with I > 2σ(I)

R int = 0.021

Refinement

R[F 2 > 2σ(F 2)] = 0.038

wR(F 2) = 0.111

S = 1.10

1097 reflections

86 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.43 e Å−3

Δρmin = −0.22 e Å−3

Data collection: RAPID-AUTO (Rigaku, 1998 ▶); cell refinement: RAPID-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2004 ▶); 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: SHELXL97.

Crystal structure: contains datablocks ptcLa, I. DOI: 10.1107/S1600536810040857/ng5044sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810040857/ng5044Isup2.hkl

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

[Na2(C8H8O8)]	F(000) = 568
Mr = 278.12	Dx = 1.917 Mg m−3
Orthorhombic, Pbcn	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2n 2ab	Cell parameters from 7116 reflections
a = 8.9053 (18) Å	θ = 3.3–27.4°
b = 8.6395 (17) Å	µ = 0.24 mm−1
c = 12.527 (3) Å	T = 293 K
V = 963.8 (3) Å3	Block, colorless
Z = 4	0.44 × 0.36 × 0.32 mm

Rigaku R-AXIS RAPID diffractometer	1097 independent reflections
Radiation source: fine-focus sealed tube	1000 reflections with I > 2σ(I)
graphite	Rint = 0.021
Detector resolution: 0 pixels mm-1	θmax = 27.4°, θmin = 3.3°
ω scan	h = −11→11
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	k = −11→11
Tmin = 0.900, Tmax = 0.925	l = −16→16
8610 measured reflections

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)] = 0.038	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.111	H atoms treated by a mixture of independent and constrained refinement
S = 1.10	w = 1/[σ2(Fo2) + (0.0658P)2 + 0.5154P] where P = (Fo2 + 2Fc2)/3
1097 reflections	(Δ/σ)max < 0.001
86 parameters	Δρmax = 0.43 e Å−3
1 restraint	Δρmin = −0.22 e Å−3

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.

	x	y	z	Uiso*/Ueq
Na	0.91916 (8)	0.06655 (8)	0.62976 (5)	0.0292 (2)
O1	1.12521 (17)	0.21959 (14)	0.69249 (10)	0.0391 (4)
O2	1.30500 (16)	0.37558 (13)	0.75029 (10)	0.0325 (3)
C1	1.19167 (19)	0.34236 (18)	0.68752 (12)	0.0243 (3)
C2	1.15019 (18)	0.46906 (17)	0.61037 (11)	0.0219 (3)
H2A	1.2386	0.4963	0.5692	0.026*
H2B	1.1207	0.5598	0.6508	0.026*
C3	1.02287 (16)	0.42768 (14)	0.53277 (10)	0.0161 (3)
H3A	0.9358	0.3927	0.5741	0.019*
C4	1.07185 (16)	0.29671 (16)	0.45770 (11)	0.0177 (3)
O3	1.01257 (15)	0.16760 (12)	0.46431 (9)	0.0300 (3)
O4	1.17325 (15)	0.33112 (14)	0.39020 (10)	0.0300 (3)
H2C	1.310 (4)	0.308 (3)	0.7989 (19)	0.088 (11)*

	U11	U22	U33	U12	U13	U23
Na	0.0336 (4)	0.0244 (4)	0.0296 (4)	−0.0038 (3)	0.0023 (3)	−0.0031 (2)
O1	0.0481 (8)	0.0278 (7)	0.0415 (7)	−0.0062 (6)	−0.0172 (6)	0.0104 (5)
O2	0.0432 (7)	0.0262 (6)	0.0282 (6)	0.0011 (5)	−0.0177 (5)	0.0041 (5)
C1	0.0305 (8)	0.0216 (7)	0.0208 (7)	0.0046 (6)	−0.0054 (6)	−0.0007 (5)
C2	0.0278 (7)	0.0185 (7)	0.0194 (7)	0.0020 (6)	−0.0054 (6)	0.0003 (5)
C3	0.0208 (7)	0.0137 (6)	0.0138 (6)	0.0032 (5)	0.0005 (5)	0.0002 (5)
C4	0.0212 (7)	0.0160 (6)	0.0159 (6)	0.0039 (5)	−0.0012 (5)	−0.0008 (5)
O3	0.0448 (7)	0.0166 (5)	0.0286 (6)	−0.0050 (5)	0.0081 (5)	−0.0041 (4)
O4	0.0340 (6)	0.0247 (6)	0.0314 (6)	−0.0026 (5)	0.0148 (5)	−0.0082 (5)

Na—O4i	2.3748 (15)	O2—H2C	0.843 (10)
Na—O1	2.3943 (15)	C1—C2	1.506 (2)
Na—O3	2.3978 (13)	C2—C3	1.536 (2)
Na—O3ii	2.4188 (13)	C2—H2A	0.9700
Na—O2iii	2.4522 (14)	C2—H2B	0.9700
Na—O1iv	2.6196 (15)	C3—C4	1.5346 (18)
Na—Naiv	3.3388 (14)	C3—C3vi	1.550 (2)
Na—Naii	3.7369 (14)	C3—H3A	0.9800
O1—C1	1.216 (2)	C4—O3	1.2368 (18)
O1—Naiv	2.6196 (15)	C4—O4	1.2723 (19)
O2—C1	1.311 (2)	O3—Naii	2.4188 (13)
O2—Nav	2.4522 (14)	O4—Navii	2.3748 (15)
O4i—Na—O1	122.39 (5)	C1—O1—Na	146.90 (11)
O4i—Na—O3	95.36 (5)	C1—O1—Naiv	123.86 (11)
O1—Na—O3	79.44 (5)	Na—O1—Naiv	83.38 (5)
O4i—Na—O3ii	119.46 (5)	C1—O2—Nav	146.49 (11)
O1—Na—O3ii	115.41 (6)	C1—O2—H2C	109 (2)
O3—Na—O3ii	78.24 (5)	Nav—O2—H2C	90 (2)
O4i—Na—O2iii	86.14 (5)	O1—C1—O2	122.32 (14)
O1—Na—O2iii	119.22 (5)	O1—C1—C2	123.18 (14)
O3—Na—O2iii	156.69 (5)	O2—C1—C2	114.49 (14)
O3ii—Na—O2iii	80.80 (5)	C1—C2—C3	114.71 (13)
O4i—Na—O1iv	76.26 (5)	C1—C2—H2A	108.6
O1—Na—O1iv	63.76 (7)	C3—C2—H2A	108.6
O3—Na—O1iv	127.10 (5)	C1—C2—H2B	108.6
O3ii—Na—O1iv	150.95 (5)	C3—C2—H2B	108.6
O2iii—Na—O1iv	75.89 (5)	H2A—C2—H2B	107.6
O4i—Na—Naiv	119.52 (4)	C4—C3—C2	110.47 (11)
O1—Na—Naiv	51.20 (4)	C4—C3—C3vi	110.16 (13)
O3—Na—Naiv	129.07 (5)	C2—C3—C3vi	109.98 (14)
O3ii—Na—Naiv	109.34 (4)	C4—C3—H3A	108.7
O2iii—Na—Naiv	68.03 (4)	C2—C3—H3A	108.7
O1iv—Na—Naiv	45.42 (3)	C3vi—C3—H3A	108.7
O4i—Na—Naii	112.22 (4)	O3—C4—O4	123.93 (13)
O1—Na—Naii	99.22 (5)	O3—C4—C3	120.17 (12)
O3—Na—Naii	39.32 (3)	O4—C4—C3	115.89 (12)
O3ii—Na—Naii	38.92 (3)	C4—O3—Na	122.30 (9)
O2iii—Na—Naii	119.06 (4)	C4—O3—Naii	127.90 (10)
O1iv—Na—Naii	162.35 (5)	Na—O3—Naii	101.76 (5)
Naiv—Na—Naii	128.23 (4)	C4—O4—Navii	144.24 (11)

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2C···O4viii	0.85 (2)	1.67 (3)	2.5097 (18)	177 (2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2C⋯O4i	0.85 (2)	1.67 (3)	2.5097 (18)	177 (2)

Symmetry code: (i) .