Poly[[[diaqua­sodium]-μ3-5-carb­oxy-2-ethyl-1H-imidazole-4-carboxyl­ato-κ4N3,O4:O5:O5] monohydrate]

Li, S.-J.; Ma, X.-T.; Song, W.-D.; Li, X.-F.; Liu, J.-H.

doi:10.1107/S1600536811002741

metal-organic compounds

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ISSN: 2056-9890

Volume 67| Part 3| March 2011| Pages m295-m296

doi:10.1107/S1600536811002741

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Poly[[[diaquasodium]-μ₃-5-carboxy-2-ethyl-1H-imidazole-4-carboxylato-κ⁴N³,O⁴:O⁵:O⁵] monohydrate]

Shi-Jie Li,^a Xiao-Tian Ma,^a Wen-Dong Song,^b ^* Xiao-Fei Li ^c and Juan-Hua Liu ^a

^aCollege of Food Science and Technology, Guangdong Ocean University, Zhanjiang 524088, People's Republic of China, ^bCollege of Science, Guangdong Ocean University, Zhanjiang 524088, People's Republic of China, and ^cCollege of Agriculture, Guangdong Ocean University, Zhanjiang 524088, People's Republic of China
^*Correspondence e-mail: songwd60@163.com

(Received 13 January 2011; accepted 20 January 2011; online 2 February 2011)

In the title complex, {[Na(C₇H₇N₂O₄)(H₂O)₂]·H₂O}_n, the Na^I atom exhibits a distorted octahedral geometry and is six-coordinated in an NO₅ environment. The equatorial plane is defined by three O atoms and one N atom from two distinct 5-carboxy-2-ethyl-1H-imidazole-4-carboxylate (H₂EIDC) ligands and one coordinated water molecule, and the apical sites are occupied by one carboxyl O atom from one H₂EIDC ligand and one O atom from the other coordinated water molecule. The Na^I atoms are linked by H₂EIDC ligands, generating an infinite double chain along the a axis. These chains are further connected via O—H⋯O and N—H⋯O hydrogen bonds into a three-dimensional supramolecular network.

Related literature

For the rational design of metal coordination complexes, see: Sava et al. (2009 ); Lu et al. (2010 ); Xue et al. (2009 ). For H₃IDC complexes with supramolecular architectures, see: Zou et al. (2006 ); Li et al. (2006 ); Sun et al. (2005 ). For related coordination polymers based on H₃EIDC, see: Wang et al. (2008 ); Zhang et al. (2010 ).

Experimental

Crystal data

[Na(C₇H₇N₂O₄)(H₂O)₂]·H₂O
M_r = 260.18
Monoclinic, P 2₁ /n
a = 8.5231 (8) Å
b = 7.0598 (7) Å
c = 19.0329 (17) Å
β = 98.880 (1)°
V = 1131.51 (18) Å³
Z = 4
Mo Kα radiation
μ = 0.17 mm⁻¹
T = 298 K
0.49 × 0.48 × 0.34 mm

Data collection

Bruker SMART 1000 CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2007 ) T_min = 0.923, T_max = 0.946
5410 measured reflections
1991 independent reflections
1549 reflections with I > 2σ(I)
R_int = 0.043

Refinement

R[F² > 2σ(F²)] = 0.039
wR(F²) = 0.109
S = 1.04
1991 reflections
162 parameters
9 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.33 e Å⁻³
Δρ_min = −0.27 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O3W—H6W⋯O2Wⁱ	0.85	2.09	2.872 (3)	154
O3W—H5W⋯O2ⁱⁱ	0.85	2.07	2.904 (3)	165
O2W—H4W⋯O3ⁱⁱ	0.85	2.04	2.888 (3)	174
O2W—H3W⋯O1ⁱⁱⁱ	0.85	1.96	2.812 (3)	174
O1W—H2W⋯O3W^iv	0.84 (1)	1.86 (1)	2.701 (3)	178 (3)
O1W—H1W⋯O1^v	0.84 (1)	2.33 (2)	3.096 (3)	152 (3)
O3—H3⋯O2	0.82	1.64	2.453 (2)	168
N2—H2⋯O1W^vi	0.86	2.01	2.857 (3)	171
Symmetry codes: (i) x-1, y, z; (ii) x, y-1, z; (iii) x+1, y-1, z; (iv) $[-x+{\script{3\over 2}}, y+{\script{1\over 2}}, -z+{\script{3\over 2}}]$ ; (v) x+1, y, z; (vi) -x+2, -y+1, -z+1.

Data collection: SMART (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT; 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/S1600536811002741/zl2345sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811002741/zl2345Isup2.hkl

checkCIF report

Comment top

The rational design and synthesis of novel metal-coordination complexes via deliberate selection of metal ions and organic ligands has attracted much attention due to the fascinating structures that can be obtained and their potential applications in catalysis, magnetism, photoluminescence and gas storage (Sava et al.,2009; Lu et al., 2010; Xue et al., 2009). The 4,5-imidazoledicarboxylic acid (H₃IDC) ligand exhibits flexible multi-functional coordination sites involving two N atoms of the imidazole ring and four carboxyl O atoms, and has been widely used to construct novel supramolecular architectures (Zou et al., 2006; Li et al., 2006; Sun et al., 2005). To augment the data for the well studied H₃IDC ligand, we recently chose to study a closely related ligand, 2-ethyl-1H-imidazole-4,5-dicarboxylic acid (H₃EIDC) with an ethyl substitutent in the 2-position of the imidazole group, which could be a good candidate for generating intriguing supramolecular networks. To the best of our knowledge, only a few coordination polymers based on the H₃EIDC ligand have been reported so far (Wang et al., 2008; Zhang et al., 2010). We report herein the hydrothermal synthesis and crystal structure of a new Na^I complex, the title compound.

As illustrated in Fig. 1, the title complex, [Na(C₇H₇N₂O₄)₂(H₂O)₂].H₂O, comprises one H₂EIDC ligand, one Na^I ion, two coordinated water molecules and one solvent water molecule. Each Na^I cation exhibits a distorted octahedral geometry and is six-coordinated by three oxygen (O4, O1ⁱ and O4ⁱⁱ) atoms and one nitrogen (Nⁱ) atom of three distinct H₂EIDC ligands and two oxygen atoms (O1W and O2W) from two coordinated water molecules (symmetry codes: i = 1-x, 1-y, 1-z; ii = 2-x, 1-y, 1-z). The equatorial plane is built by the O4, O1ⁱ, O1W and N1ⁱ atoms and the apical positions are occupied by O2W and O4ⁱⁱ. Two adjacent Na centers are bridged by two carboxyl oxygen atoms to form a Na₂O₂ subunit with a Na—Na distance of 3.684 (2) Å, and the Na₂O₂ subunits are linked by H₂EIDC ligands to generate a one-dimensional double chain propagating along the a axis (Fig. 2a). The adjacent one-dimensional chains are connected into a three-dimensional supramolecular structure (Fig. 2 b) via N—H···O and O—H···O hydrogen bonds involving the uncoordinated imidazole N atoms, the uncoordinated and coordinated carboxylate O atoms from the H₂EIDC ligands and the uncoordinated and coordinated water molecules (Table 1).

Related literature top

For the rational design of metal coordination complexes, see: Sava et al. (2009); Lu et al. (2010); Xue et al. (2009). For H₃IDC complexes with supramolecular architectures, see: Zou et al. (2006); Li et al. (2006); Sun et al. (2005). For related coordination polymers based on H₃EIDC, see: Wang et al. (2008); Zhang et al. (2010).

Experimental top

A mixture of NaOH (0.1 mmol, 0.004 g) and 2-ethyl-1H-imidazole-4,5-dicarboxylic acid (0.5 mmol, 0.9 g) in 10 ml of H₂O was sealed in an autoclave equipped with a Teflon liner (20 ml) and then heated to 433 K for 4 days. Colorless crystals were obtained by slow evaporation of the solvent at room temperature with a yield of 42% based on NaOH.

Computing details top

Data collection: SMART (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); 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. The structure of the title compound, showing the atomic numbering scheme. Non-H atoms are shown with 30% probability displacement ellipsoids. (symmetry codes: i = 1-x, 1-y, 1-z; ii = 2-x, 1-y, 1-z).
	Fig. 2. (a) One-dimensional double chain constructed of Na₂O₂ subunits and H₂EIDC ligands propagating along the a axis (H atoms are omitted for clarity); (b) A view of the three-dimensional network constructed by O—H···O and N—H···O hydrogen bonding interactions (H atoms not involved in the hydrogen bonds are omitted for clarity).

Poly[[[diaquasodium]-µ₃-5-carboxy-2-ethyl-1H- imidazole-4-carboxylato-κ⁴N³,O⁴:O⁵:O⁵] monohydrate] top

Crystal data top

[Na(C₇H₇N₂O₄)(H₂O)₂]·H₂O	F(000) = 544
M_r = 260.18	D_x = 1.527 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 1702 reflections
a = 8.5231 (8) Å	θ = 2.5–25.9°
b = 7.0598 (7) Å	µ = 0.17 mm⁻¹
c = 19.0329 (17) Å	T = 298 K
β = 98.880 (1)°	Block, colorless
V = 1131.51 (18) Å³	0.49 × 0.48 × 0.34 mm
Z = 4

Data collection top

Bruker SMART 1000 CCD area-detector diffractometer	1991 independent reflections
Radiation source: fine-focus sealed tube	1549 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.043
ϕ and ω scans	θ_max = 25.0°, θ_min = 2.5°
Absorption correction: multi-scan (SADABS; Bruker, 2007)	h = −6→10
T_min = 0.923, T_max = 0.946	k = −8→8
5410 measured reflections	l = −22→21

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.039	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.109	w = 1/[σ²(F_o²) + (0.0431P)² + 0.658P] where P = (F_o² + 2F_c²)/3
S = 1.04	(Δ/σ)_max < 0.001
1991 reflections	Δρ_max = 0.33 e Å⁻³
162 parameters	Δρ_min = −0.27 e Å⁻³
9 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.116 (7)

Crystal data top

[Na(C₇H₇N₂O₄)(H₂O)₂]·H₂O	V = 1131.51 (18) Å³
M_r = 260.18	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 8.5231 (8) Å	µ = 0.17 mm⁻¹
b = 7.0598 (7) Å	T = 298 K
c = 19.0329 (17) Å	0.49 × 0.48 × 0.34 mm
β = 98.880 (1)°

Data collection top

Bruker SMART 1000 CCD area-detector diffractometer	1991 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2007)	1549 reflections with I > 2σ(I)
T_min = 0.923, T_max = 0.946	R_int = 0.043
5410 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.039	9 restraints
wR(F²) = 0.109	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	Δρ_max = 0.33 e Å⁻³
1991 reflections	Δρ_min = −0.27 e Å⁻³
162 parameters

Special details top

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 (Å²) top

	x	y	z	U_iso*/U_eq
Na1	0.93820 (11)	0.32398 (16)	0.56175 (5)	0.0388 (4)
N1	0.3469 (2)	0.7014 (3)	0.42293 (10)	0.0288 (5)
N2	0.5987 (2)	0.6488 (3)	0.41437 (10)	0.0283 (5)
H2	0.6816	0.6165	0.3966	0.034*
O1	0.2192 (2)	0.8220 (3)	0.54163 (10)	0.0413 (5)
O2	0.4583 (2)	0.8601 (3)	0.60539 (9)	0.0361 (5)
O3	0.7371 (2)	0.8029 (3)	0.59418 (9)	0.0361 (5)
H3	0.6453	0.8360	0.5953	0.054*
O4	0.8713 (2)	0.6644 (3)	0.51722 (9)	0.0374 (5)
O1W	1.1322 (2)	0.5012 (3)	0.63961 (10)	0.0413 (5)
H1W	1.132 (4)	0.608 (2)	0.6204 (13)	0.062*
H2W	1.152 (4)	0.509 (4)	0.6843 (6)	0.062*
O2W	1.0214 (2)	0.0314 (3)	0.61812 (10)	0.0444 (6)
H3W	1.0861	−0.0263	0.5958	0.067*
H4W	0.9347	−0.0303	0.6128	0.067*
O3W	0.3117 (3)	0.0343 (4)	0.71733 (11)	0.0803 (9)
H5W	0.3704	−0.0161	0.6902	0.120*
H6W	0.2135	0.0274	0.7005	0.120*
C1	0.3656 (3)	0.8138 (4)	0.54743 (13)	0.0292 (6)
C2	0.4401 (3)	0.7466 (3)	0.48677 (12)	0.0256 (6)
C3	0.5973 (3)	0.7131 (3)	0.48215 (12)	0.0255 (6)
C4	0.7464 (3)	0.7262 (4)	0.53360 (13)	0.0277 (6)
C5	0.4475 (3)	0.6448 (4)	0.38032 (13)	0.0280 (6)
C6	0.4053 (3)	0.5841 (5)	0.30430 (13)	0.0391 (7)
H6A	0.4522	0.4610	0.2986	0.047*
H6B	0.4512	0.6731	0.2744	0.047*
C7	0.2284 (3)	0.5722 (5)	0.27913 (15)	0.0472 (8)
H7A	0.1832	0.4770	0.3059	0.071*
H7B	0.2094	0.5397	0.2296	0.071*
H7C	0.1804	0.6925	0.2859	0.071*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Na1	0.0261 (6)	0.0525 (8)	0.0381 (6)	0.0021 (5)	0.0057 (4)	−0.0010 (5)
N1	0.0239 (11)	0.0336 (12)	0.0288 (11)	0.0004 (9)	0.0038 (9)	0.0000 (9)
N2	0.0228 (11)	0.0363 (13)	0.0270 (11)	0.0012 (9)	0.0083 (8)	−0.0012 (9)
O1	0.0241 (10)	0.0583 (13)	0.0433 (11)	0.0016 (9)	0.0107 (8)	−0.0118 (10)
O2	0.0295 (10)	0.0503 (12)	0.0289 (10)	0.0009 (8)	0.0057 (7)	−0.0098 (8)
O3	0.0243 (9)	0.0520 (13)	0.0319 (10)	0.0009 (8)	0.0033 (7)	−0.0077 (9)
O4	0.0229 (10)	0.0517 (13)	0.0379 (10)	0.0049 (8)	0.0061 (8)	−0.0022 (9)
O1W	0.0422 (11)	0.0494 (13)	0.0332 (10)	0.0032 (10)	0.0086 (9)	−0.0007 (9)
O2W	0.0342 (10)	0.0526 (13)	0.0464 (12)	0.0014 (9)	0.0062 (8)	−0.0099 (10)
O3W	0.0568 (15)	0.148 (3)	0.0359 (12)	0.0132 (16)	0.0053 (10)	−0.0115 (15)
C1	0.0279 (14)	0.0297 (14)	0.0312 (14)	−0.0002 (11)	0.0082 (11)	0.0000 (11)
C2	0.0246 (12)	0.0257 (13)	0.0272 (12)	−0.0007 (10)	0.0056 (10)	0.0015 (10)
C3	0.0257 (13)	0.0260 (13)	0.0255 (12)	−0.0001 (10)	0.0060 (10)	0.0000 (10)
C4	0.0255 (13)	0.0291 (14)	0.0293 (13)	−0.0002 (11)	0.0062 (10)	0.0011 (11)
C5	0.0266 (13)	0.0307 (14)	0.0272 (13)	0.0003 (10)	0.0054 (10)	0.0006 (11)
C6	0.0391 (16)	0.0506 (19)	0.0275 (14)	−0.0012 (13)	0.0048 (11)	−0.0024 (13)
C7	0.0446 (17)	0.058 (2)	0.0351 (15)	−0.0049 (15)	−0.0052 (12)	0.0008 (14)

Geometric parameters (Å, º) top

Na1—O4ⁱ	2.378 (2)	O4—Na1ⁱ	2.378 (2)
Na1—O2W	2.384 (2)	O1W—H1W	0.840 (11)
Na1—O1W	2.396 (2)	O1W—H2W	0.843 (11)
Na1—O1ⁱⁱ	2.433 (2)	O2W—H3W	0.8500
Na1—N1ⁱⁱ	2.498 (2)	O2W—H4W	0.8500
Na1—O4	2.583 (2)	O3W—H5W	0.8500
N1—C5	1.329 (3)	O3W—H6W	0.8499
N1—C2	1.383 (3)	C1—C2	1.480 (3)
N1—Na1ⁱⁱ	2.498 (2)	C2—C3	1.377 (3)
N2—C5	1.351 (3)	C3—C4	1.482 (3)
N2—C3	1.369 (3)	C5—C6	1.499 (3)
N2—H2	0.8600	C6—C7	1.512 (4)
O1—C1	1.237 (3)	C6—H6A	0.9700
O1—Na1ⁱⁱ	2.432 (2)	C6—H6B	0.9700
O2—C1	1.296 (3)	C7—H7A	0.9600
O3—C4	1.287 (3)	C7—H7B	0.9600
O3—H3	0.8200	C7—H7C	0.9600
O4—C4	1.234 (3)

O4ⁱ—Na1—O2W	97.45 (7)	Na1—O1W—H2W	132 (2)
O4ⁱ—Na1—O1W	84.24 (7)	H1W—O1W—H2W	111.4 (15)
O2W—Na1—O1W	92.58 (7)	Na1—O2W—H3W	111.2
O4ⁱ—Na1—O1ⁱⁱ	81.27 (7)	Na1—O2W—H4W	101.4
O2W—Na1—O1ⁱⁱ	94.91 (8)	H3W—O2W—H4W	108.2
O1W—Na1—O1ⁱⁱ	164.44 (8)	H5W—O3W—H6W	112.6
O4ⁱ—Na1—N1ⁱⁱ	147.95 (8)	O1—C1—O2	122.6 (2)
O2W—Na1—N1ⁱⁱ	96.45 (8)	O1—C1—C2	119.6 (2)
O1W—Na1—N1ⁱⁱ	123.79 (8)	O2—C1—C2	117.8 (2)
O1ⁱⁱ—Na1—N1ⁱⁱ	68.86 (7)	C3—C2—N1	109.7 (2)
O4ⁱ—Na1—O4	84.16 (7)	C3—C2—C1	130.1 (2)
O2W—Na1—O4	171.50 (8)	N1—C2—C1	120.1 (2)
O1W—Na1—O4	79.24 (7)	N2—C3—C2	105.48 (19)
O1ⁱⁱ—Na1—O4	93.59 (7)	N2—C3—C4	120.8 (2)
N1ⁱⁱ—Na1—O4	86.31 (7)	C2—C3—C4	133.7 (2)
O4ⁱ—Na1—Na1ⁱ	44.22 (5)	O4—C4—O3	123.3 (2)
O2W—Na1—Na1ⁱ	140.98 (7)	O4—C4—C3	119.7 (2)
O1W—Na1—Na1ⁱ	78.72 (6)	O3—C4—C3	116.9 (2)
O1ⁱⁱ—Na1—Na1ⁱ	86.90 (6)	N1—C5—N2	111.0 (2)
N1ⁱⁱ—Na1—Na1ⁱ	120.13 (7)	N1—C5—C6	126.4 (2)
O4—Na1—Na1ⁱ	39.94 (4)	N2—C5—C6	122.6 (2)
C5—N1—C2	105.55 (19)	C5—C6—C7	113.6 (2)
C5—N1—Na1ⁱⁱ	141.28 (17)	C5—C6—H6A	108.8
C2—N1—Na1ⁱⁱ	110.58 (15)	C7—C6—H6A	108.8
C5—N2—C3	108.2 (2)	C5—C6—H6B	108.8
C5—N2—H2	125.9	C7—C6—H6B	108.8
C3—N2—H2	125.9	H6A—C6—H6B	107.7
C1—O1—Na1ⁱⁱ	118.37 (16)	C6—C7—H7A	109.5
C4—O3—H3	109.5	C6—C7—H7B	109.5
C4—O4—Na1ⁱ	147.92 (17)	H7A—C7—H7B	109.5
C4—O4—Na1	113.65 (16)	C6—C7—H7C	109.5
Na1ⁱ—O4—Na1	95.84 (7)	H7A—C7—H7C	109.5
Na1—O1W—H1W	104 (2)	H7B—C7—H7C	109.5

O4ⁱ—Na1—O4—C4	167.0 (2)	N1—C2—C3—N2	0.6 (3)
O1W—Na1—O4—C4	−107.73 (17)	C1—C2—C3—N2	178.7 (2)
O1ⁱⁱ—Na1—O4—C4	86.20 (17)	N1—C2—C3—C4	−176.6 (3)
N1ⁱⁱ—Na1—O4—C4	17.68 (17)	C1—C2—C3—C4	1.5 (5)
Na1ⁱ—Na1—O4—C4	167.0 (2)	Na1ⁱ—O4—C4—O3	−121.0 (3)
O4ⁱ—Na1—O4—Na1ⁱ	0.0	Na1—O4—C4—O3	83.8 (3)
O1W—Na1—O4—Na1ⁱ	85.23 (7)	Na1ⁱ—O4—C4—C3	59.2 (4)
O1ⁱⁱ—Na1—O4—Na1ⁱ	−80.84 (7)	Na1—O4—C4—C3	−96.0 (2)
N1ⁱⁱ—Na1—O4—Na1ⁱ	−149.36 (8)	N2—C3—C4—O4	−5.9 (4)
Na1ⁱⁱ—O1—C1—O2	−168.77 (19)	C2—C3—C4—O4	171.0 (3)
Na1ⁱⁱ—O1—C1—C2	10.4 (3)	N2—C3—C4—O3	174.3 (2)
C5—N1—C2—C3	−1.1 (3)	C2—C3—C4—O3	−8.9 (4)
Na1ⁱⁱ—N1—C2—C3	164.78 (16)	C2—N1—C5—N2	1.1 (3)
C5—N1—C2—C1	−179.3 (2)	Na1ⁱⁱ—N1—C5—N2	−157.43 (19)
Na1ⁱⁱ—N1—C2—C1	−13.5 (3)	C2—N1—C5—C6	−178.6 (3)
O1—C1—C2—C3	−175.0 (3)	Na1ⁱⁱ—N1—C5—C6	22.8 (5)
O2—C1—C2—C3	4.3 (4)	C3—N2—C5—N1	−0.7 (3)
O1—C1—C2—N1	2.9 (4)	C3—N2—C5—C6	179.0 (2)
O2—C1—C2—N1	−177.8 (2)	N1—C5—C6—C7	−5.9 (4)
C5—N2—C3—C2	0.0 (3)	N2—C5—C6—C7	174.4 (2)
C5—N2—C3—C4	177.7 (2)

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O3W—H6W···O2Wⁱⁱⁱ	0.85	2.09	2.872 (3)	154
O3W—H5W···O2^iv	0.85	2.07	2.904 (3)	165
O2W—H4W···O3^iv	0.85	2.04	2.888 (3)	174
O2W—H3W···O1^v	0.85	1.96	2.812 (3)	174
O1W—H2W···O3W^vi	0.84 (1)	1.86 (1)	2.701 (3)	178 (3)
O1W—H1W···O1^vii	0.84 (1)	2.33 (2)	3.096 (3)	152 (3)
O3—H3···O2	0.82	1.64	2.453 (2)	168
N2—H2···O1Wⁱ	0.86	2.01	2.857 (3)	171

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

Experimental details

Crystal data
Chemical formula	[Na(C₇H₇N₂O₄)(H₂O)₂]·H₂O
M_r	260.18
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	298
a, b, c (Å)	8.5231 (8), 7.0598 (7), 19.0329 (17)
β (°)	98.880 (1)
V (Å³)	1131.51 (18)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.17
Crystal size (mm)	0.49 × 0.48 × 0.34

Data collection
Diffractometer	Bruker SMART 1000 CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2007)
T_min, T_max	0.923, 0.946
No. of measured, independent and observed [I > 2σ(I)] reflections	5410, 1991, 1549
R_int	0.043
(sin θ/λ)_max (Å⁻¹)	0.594

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.039, 0.109, 1.04
No. of reflections	1991
No. of parameters	162
No. of restraints	9
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.33, −0.27

Computer programs: SMART (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O3W—H6W···O2Wⁱ	0.85	2.09	2.872 (3)	154
O3W—H5W···O2ⁱⁱ	0.85	2.07	2.904 (3)	165
O2W—H4W···O3ⁱⁱ	0.85	2.04	2.888 (3)	174
O2W—H3W···O1ⁱⁱⁱ	0.85	1.96	2.812 (3)	174
O1W—H2W···O3W^iv	0.843 (11)	1.859 (12)	2.701 (3)	178 (3)
O1W—H1W···O1^v	0.840 (11)	2.326 (17)	3.096 (3)	152 (3)
O3—H3···O2	0.82	1.64	2.453 (2)	168
N2—H2···O1W^vi	0.86	2.01	2.857 (3)	171

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

Acknowledgements

The work was supported by the Nonprofit Industry Foundation of the National Ocean Administration of China (grant No. 2000905021), the Guangdong Ocean Fisheries Technology Promotion Project [grant No. A2009003–018(c)], the Guangdong Chinese Academy of Science Comprehensive Strategic Cooperation Project (grant No. 2009B091300121), the Guangdong Province Key Project in the Field of Social Development [grant No. A2009011–007(c)], the Science and Technology Department of Guangdong Province Project (grant No. 00087 061110314018) and the Guangdong Natural Science Fundation (No. 9252408801000002).

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