Poly[(μ(5)-2-methyl-3,5-dinitro-benzoato)sodium].

In the crystal of the title coordination polymer, [Na(C(8)H(5)N(2)O(6))](n), the Na(I) ion is linked to five nearby anions. Their bonding modes are three monodentate carboxyl-ate O atoms, one O,O'-bidentate carboxyl-ate group and one O,O'-bidentate nitro group. This results in an irregular NaO(7) coordination geometry for the metal ion. This connectivity leads to a layered network propagating in (100).

Related literature

For the structure of a trimethyl-tin complex with the ortho-toluate ligand, see: Danish et al. (2010 ▶).

Experimental

Crystal data

[Na(C8H5N2O6)]

M = 248.13

Orthorhombic,

a = 27.8428 (13) Å

b = 10.452 (2) Å

c = 6.642 (6) Å

V = 1932.8 (17) Å3

Z = 8

Mo Kα radiation

μ = 0.18 mm−1

T = 293 K

0.42 × 0.14 × 0.08 mm

Data collection

Kuma KM-4 four-circle diffractometer

Absorption correction: analytical (CrysAlis RED; Oxford Diffraction, 2008 ▶) T min = 0.975, T max = 0.984

2659 measured reflections

2406 independent reflections

1273 reflections with I > 2σ(I)

R int = 0.047

3 standard reflections every 200 reflections intensity decay: 0.01%

Refinement

R[F 2 > 2σ(F 2)] = 0.037

wR(F 2) = 0.132

S = 1.00

2406 reflections

155 parameters

H-atom parameters constrained

Δρmax = 0.33 e Å−3

Δρmin = −0.30 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: SHELXL97.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810000498/hb5280sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810000498/hb5280Isup2.hkl

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

[Na(C8H5N2O6)]	Dx = 1.705 Mg m−3
Mr = 248.13	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, Pbcn	Cell parameters from 25 reflections
a = 27.8428 (13) Å	θ = 6–15°
b = 10.452 (2) Å	µ = 0.18 mm−1
c = 6.642 (6) Å	T = 293 K
V = 1932.8 (17) Å3	Needle, yellow
Z = 8	0.42 × 0.14 × 0.08 mm
F(000) = 1008

Kuma KM-4 four-circle diffractometer	1273 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.047
graphite	θmax = 29.1°, θmin = 1.5°
profile data from ω/2θ scans	h = 0→36
Absorption correction: analytical (CrysAlis RED; Oxford Diffraction, 2008)	k = −14→1
Tmin = 0.975, Tmax = 0.984	l = 0→9
2659 measured reflections	3 standard reflections every 200 reflections
2406 independent reflections	intensity decay: 0.01%

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)] = 0.037	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.132	H-atom parameters constrained
S = 1.00	w = 1/[σ2(Fo2) + (0.0681P)2 + 0.6169P] where P = (Fo2 + 2Fc2)/3
2406 reflections	(Δ/σ)max = 0.001
155 parameters	Δρmax = 0.33 e Å−3
0 restraints	Δρmin = −0.30 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
Na1	0.95606 (3)	−0.10192 (7)	0.92650 (12)	0.0318 (2)
O2	0.96094 (6)	0.14635 (16)	1.0752 (2)	0.0389 (4)
O11	0.75046 (8)	0.2906 (2)	0.8738 (4)	0.0747 (7)
O1	0.93442 (7)	0.10334 (16)	0.7707 (3)	0.0482 (5)
N1	0.77183 (7)	0.3679 (2)	0.9765 (4)	0.0427 (5)
C1	0.90187 (7)	0.28318 (18)	0.9385 (3)	0.0246 (4)
C7	0.93555 (7)	0.16846 (18)	0.9265 (3)	0.0268 (4)
C5	0.89172 (7)	0.50978 (19)	0.9440 (3)	0.0273 (4)
C3	0.82465 (7)	0.3756 (2)	0.9576 (3)	0.0294 (5)
C2	0.85223 (7)	0.26469 (19)	0.9491 (3)	0.0283 (5)
C4	0.84279 (7)	0.4982 (2)	0.9550 (3)	0.0287 (4)
H4	0.8228	0.5695	0.9604	0.034*
C6	0.92178 (8)	0.40496 (18)	0.9386 (3)	0.0273 (4)
H6	0.9549	0.4157	0.9350	0.033*
C8	0.83187 (9)	0.1325 (2)	0.9644 (5)	0.0479 (7)
H8A	0.8039	0.1339	1.0489	0.072*
H8B	0.8555	0.0762	1.0214	0.072*
H8C	0.8232	0.1027	0.8326	0.072*
O12	0.75280 (7)	0.4416 (2)	1.0929 (3)	0.0605 (6)
N2	0.91229 (7)	0.63855 (17)	0.9404 (3)	0.0328 (4)
O21	0.88557 (7)	0.72989 (15)	0.9215 (3)	0.0461 (5)
O22	0.95584 (7)	0.64912 (16)	0.9575 (3)	0.0537 (5)

	U11	U22	U33	U12	U13	U23
Na1	0.0349 (5)	0.0263 (4)	0.0341 (5)	−0.0013 (3)	0.0000 (4)	0.0016 (3)
O2	0.0341 (9)	0.0433 (9)	0.0392 (9)	0.0091 (7)	−0.0041 (7)	0.0086 (7)
O11	0.0389 (9)	0.0753 (15)	0.1098 (19)	−0.0043 (11)	−0.0178 (13)	−0.0198 (15)
O1	0.0640 (12)	0.0410 (9)	0.0396 (10)	0.0191 (9)	0.0004 (9)	−0.0092 (8)
N1	0.0259 (9)	0.0409 (10)	0.0614 (14)	0.0058 (8)	−0.0002 (10)	0.0064 (11)
C1	0.0269 (9)	0.0237 (8)	0.0233 (10)	0.0025 (7)	−0.0026 (9)	0.0012 (8)
C7	0.0245 (9)	0.0250 (9)	0.0309 (11)	0.0025 (8)	0.0038 (9)	0.0057 (9)
C5	0.0373 (11)	0.0244 (9)	0.0204 (9)	−0.0007 (8)	−0.0007 (9)	0.0008 (8)
C3	0.0257 (10)	0.0349 (11)	0.0276 (10)	0.0022 (8)	−0.0011 (8)	−0.0009 (9)
C2	0.0275 (10)	0.0283 (10)	0.0292 (11)	−0.0004 (8)	−0.0018 (9)	0.0014 (9)
C4	0.0332 (9)	0.0294 (9)	0.0235 (10)	0.0085 (9)	0.0002 (9)	0.0016 (8)
C6	0.0291 (10)	0.0279 (9)	0.0247 (10)	−0.0015 (8)	−0.0004 (8)	0.0018 (9)
C8	0.0372 (12)	0.0314 (11)	0.0751 (19)	−0.0062 (10)	0.0010 (14)	0.0028 (12)
O12	0.0391 (9)	0.0542 (11)	0.0881 (15)	0.0131 (9)	0.0199 (11)	0.0039 (12)
N2	0.0467 (11)	0.0250 (8)	0.0266 (9)	−0.0013 (8)	0.0019 (9)	0.0017 (7)
O21	0.0611 (12)	0.0252 (7)	0.0518 (11)	0.0044 (7)	−0.0022 (10)	0.0003 (7)
O22	0.0440 (10)	0.0352 (9)	0.0819 (14)	−0.0116 (8)	0.0011 (10)	0.0017 (9)

Na1—O1	2.4567 (19)	C1—C2	1.397 (3)
Na1—O2	2.780 (2)	C1—C7	1.524 (3)
Na1—O2i	2.3571 (17)	C5—C4	1.370 (3)
Na1—O1ii	2.364 (3)	C5—C6	1.379 (3)
Na1—O2iii	2.383 (3)	C5—N2	1.463 (3)
Na1—O22iv	2.6102 (19)	C3—C4	1.377 (3)
Na1—O21iv	2.635 (2)	C3—C2	1.392 (3)
Na1—Na1i	3.3881 (17)	C2—C8	1.497 (3)
Na1—Na1v	3.389 (2)	C4—H4	0.9300
Na1—Na1iii	3.946 (3)	C6—H6	0.9300
O2—C7	1.237 (3)	C8—H8A	0.9600
O2—Na1i	2.3571 (17)	C8—H8B	0.9600
O2—Na1ii	2.383 (3)	C8—H8C	0.9600
O11—N1	1.213 (3)	N2—O21	1.217 (2)
O1—C7	1.239 (3)	N2—O22	1.223 (2)
O1—Na1iii	2.364 (3)	N2—Na1vi	2.975 (2)
N1—O12	1.212 (3)	O21—Na1vi	2.635 (2)
N1—C3	1.478 (3)	O22—Na1vi	2.6102 (19)
C1—C6	1.388 (3)
O2i—Na1—O1ii	104.67 (7)	C6—C1—C2	121.45 (18)
O2i—Na1—O2iii	84.31 (7)	C6—C1—C7	118.39 (18)
O1ii—Na1—O2iii	163.77 (7)	C2—C1—C7	120.16 (17)
O2i—Na1—O1	114.23 (7)	O2—C7—O1	125.38 (19)
O1ii—Na1—O1	110.50 (7)	O2—C7—C1	117.19 (18)
O2iii—Na1—O1	76.81 (7)	O1—C7—C1	117.40 (18)
O2i—Na1—O22iv	78.83 (6)	C4—C5—C6	122.34 (19)
O1ii—Na1—O22iv	85.23 (7)	C4—C5—N2	118.12 (18)
O2iii—Na1—O22iv	83.28 (7)	C6—C5—N2	119.53 (19)
O1—Na1—O22iv	154.57 (7)	C4—C3—C2	124.91 (19)
O2i—Na1—O21iv	126.78 (6)	C4—C3—N1	114.59 (18)
O1ii—Na1—O21iv	79.53 (6)	C2—C3—N1	120.47 (19)
O2iii—Na1—O21iv	84.27 (6)	C3—C2—C1	115.62 (18)
O1—Na1—O21iv	113.24 (7)	C3—C2—C8	123.86 (19)
O22iv—Na1—O21iv	48.26 (6)	C1—C2—C8	120.38 (18)
O2i—Na1—O2	97.91 (6)	C5—C4—C3	116.57 (19)
O1ii—Na1—O2	71.01 (6)	C5—C4—H4	121.7
O2iii—Na1—O2	121.81 (6)	C3—C4—H4	121.7
O1—Na1—O2	49.20 (6)	C5—C6—C1	119.07 (19)
O22iv—Na1—O2	154.51 (7)	C5—C6—H6	120.5
O21iv—Na1—O2	131.58 (6)	C1—C6—H6	120.5
C7—O2—Na1i	126.39 (14)	C2—C8—H8A	109.5
C7—O2—Na1ii	141.83 (14)	C2—C8—H8B	109.5
Na1i—O2—Na1ii	91.28 (6)	H8A—C8—H8B	109.5
C7—O2—Na1	82.10 (12)	C2—C8—H8C	109.5
Na1i—O2—Na1	82.09 (6)	H8A—C8—H8C	109.5
Na1ii—O2—Na1	99.40 (6)	H8B—C8—H8C	109.5
C7—O1—Na1iii	143.56 (16)	O21—N2—O22	123.02 (18)
C7—O1—Na1	97.00 (14)	O21—N2—C5	118.96 (19)
Na1iii—O1—Na1	109.83 (7)	O22—N2—C5	118.02 (17)
O12—N1—O11	124.5 (2)	N2—O21—Na1vi	93.83 (13)
O12—N1—C3	117.0 (2)	N2—O22—Na1vi	94.88 (13)
O11—N1—C3	118.5 (2)

Table 1

Selected bond lengths (Å)

Na1—O1	2.4567 (19)
Na1—O2	2.780 (2)
Na1—O2i	2.3571 (17)
Na1—O1ii	2.364 (3)
Na1—O2iii	2.383 (3)
Na1—O22iv	2.6102 (19)
Na1—O21iv	2.635 (2)

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) .