Poly[[μ2-aqua-μ3-(4-carb­oxy-2-propyl-1H-imidazole-5-carboxyl­ato-κ4
               N
               3,O
               4:O
               4:O
               5)-sodium] hemihydrate]

doi:10.1107/S1600536811007732

Acta Crystallogr Sect E Struct Rep Online. 2011 April 1; 67(Pt 4): m408.

Published online 2011 March 9. doi: 10.1107/S1600536811007732

PMCID: PMC3099890

Poly[[μ₂-aqua-μ₃-(4-carboxy-2-propyl-1H-imidazole-5-carboxylato-κ⁴ N ³,O ⁴:O ⁴:O ⁵)-sodium] hemihydrate]

Zhong-Jing Huang,^a^* Jin-Niu Tang,^a Zhi-Rong Luo,^a Dai-Yin Wang,^a and Huan Wei^a

^aDepartment of Chemistry, Guangxi University for Nationalities, Nanning 530006, People’s Republic of China

Correspondence e-mail: huangzhongjing1/at/yahoo.com.cn

Received January 17, 2011; Accepted March 1, 2011.

This is an open-access article distributed under the terms of the Creative Commons Attribution Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

Abstract

In the title compound, {[Na(C₈H₉N₂O₄)(H₂O)]·0.5H₂O}_n, the Na⁺ ion is coordinated by two bridging water molecules, one N atom and three O atoms from three 4-carboxy-2-propyl-1H-imidazole-5-carboxylate (H₂pimdc) ligands. Adjacent Na⁺ ions are linked alternately by two water O atoms and two carboxy O atoms into a chain along [001]. These chains are connected through the coordination of the carboxylate O atoms to the Na⁺ ions, forming a three-dimensional structure. An intramolecular O—H (...)

O hydrogen bond and intermolecular N—H (...)

O and O—H

O hydrogen bonds are present in the crystal structure.

Related literature

For the properties and biological activity of imidazole-4,5-dicarboxylic acid and its derivatives, see: Baures (1999

); Bogdanova et al. (1992

); Borodkin et al. (1984

); Reichardt et al. (1992

); Su et al. (2001

An external file that holds a picture, illustration, etc.
Object name is e-67-0m408-scheme1.jpg Object name is e-67-0m408-scheme1.jpg

Experimental

Crystal data

[Na(C₈H₉N₂O₄)(H₂O)]·0.5H₂O
M _r = 247.18
Monoclinic,
a = 15.406 (4) Å
b = 15.478 (4) Å
c = 10.734 (3) Å
β = 118.364 (3)°
V = 2252.4 (9) Å³
Z = 8
Mo Kα radiation
μ = 0.15 mm⁻¹
T = 296 K
0.52 × 0.47 × 0.44 mm

Data collection

Bruker APEX CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T _min = 0.528, T _max = 0.562
5971 measured reflections
1986 independent reflections
1669 reflections with I > 2σ(I)
R _int = 0.020

Refinement

R[F ² > 2σ(F ²)] = 0.034
wR(F ²) = 0.106
S = 1.10
1986 reflections
152 parameters
H-atom parameters constrained
Δρ_max = 0.23 e Å⁻³
Δρ_min = −0.21 e Å⁻³

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: DIAMOND (Brandenburg, 1999

); software used to prepare material for publication: SHELXTL (Sheldrick, 2008

Table 1

Selected bond lengths (Å)

Table 2

Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811007732/hy2402sup1.cif

Click here to view.^{(19K, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811007732/hy2402Isup2.hkl

Click here to view.^{(98K, hkl)}

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

Acknowledgments

This work was supported by the Innovation Project of Guangxi University for Nationalities (gxun-chx2010083).

supplementary crystallographic information

Comment

1H-Imidazole and its derivatives are a kind of excellent supramolecular synthons. The N atoms of imidazole can coordinate to metal ions in monodentate or bidentate mode (Su et al., 2001). Imidazole-4,5-dicarboxylic acid and derivatives have been studied in terms of their physical properties as well as for their diverse biological activities (Bogdanova et al., 1992; Borodkin et al., 1984; Reichardt et al., 1992), including the use of imidazole-4,5-dicarboxylic acid amides in the development of human immunodeficiency virus (HIV-1) protease inhibitors (Baures, 1999). Here we present the synthesis and structure of the title complex derived from 2-propyl-1H-imidazole-4,5-dicarboxylic acid. The distinct binding modes of the ligands as well as the coordination preferences of the metal ion are discussed.

In the title compound, the 2-propyl-4-carboxy-1H-imidazole-5-carboxylate (H₂pimdc) ligand is bonded to Na ions in a µ₃-mode. The coordination of Na ion is achieved by two water molecules, one N atom and three O atoms from three H₂pimdc ligands (Fig .1, Table 1). Two O1 atoms of the H₂pimdc ligand bridge two Na atoms, forming a parallelogram and two O5 atoms of the water molecules form another parallelogram with two Na atoms, leading to a chain along [0 0 1]. The chains are connected through the coordination of the carboxylate O3 atoms to the Na ions, forming a three-dimensional structure (Fig. 2). The propyl group becomes an ornament in the coordination network. The crystal structure is stabilized by intramolecular O—H···O hydrogen bond and intermolecular N—H···O and O—H···O hydrogen bonds (Table 2).

Experimental

An ethanol solution (5 ml) containing 2-propyl-1H-imidazole-4,5-dicarboxylic acid (1 mmol, 0.198 g) was added dropwise to a water solution (10 ml) containing NaOH (0.5 mmol, 0.040 g). After stirring for 6 h, the solution was filtered. The filtered solution were evaporated for several days in air and colorless block-shaped crystals suitable for single-crystal X-ray diffraction were obtained (yield: 80% based on the ligand).

Figures

Fig. 1.

The structure of the title compound. Displacement ellipsoids are drawn at the 30% probability level. Dashed lines denote hydrogen bonds. [Symmetry codes: (i) -x, y, 1/2-z; (ii) 1/2-x, 1/2-y, 1-z; (iii) -x, -y, 1-z.]

Fig. 2.

Crystal packing of the title compound viewed along the c axis.

Crystal data

[Na(C₈H₉N₂O₄)(H₂O)]·0.5H₂O	F(000) = 1032
M_r = 247.18	D_x = 1.458 Mg m⁻³
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 2142 reflections
a = 15.406 (4) Å	θ = 2.4–26.8°
b = 15.478 (4) Å	µ = 0.15 mm⁻¹
c = 10.734 (3) Å	T = 296 K
β = 118.364 (3)°	Block, colorless
V = 2252.4 (9) Å³	0.52 × 0.47 × 0.44 mm
Z = 8

Data collection

Bruker APEX CCD diffractometer	1986 independent reflections
Radiation source: fine-focus sealed tube	1669 reflections with I > 2σ(I)
graphite	R_int = 0.020
and ω scans	θ_max = 25.0°, θ_min = 2.0°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −18→17
T_min = 0.528, T_max = 0.562	k = −18→17
5971 measured reflections	l = −11→12

Refinement

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)] = 0.034	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.106	H-atom parameters constrained
S = 1.10	w = 1/[σ²(F_o²) + (0.0609P)² + 0.6897P] where P = (F_o² + 2F_c²)/3
1986 reflections	(Δ/σ)_max < 0.001
152 parameters	Δρ_max = 0.23 e Å⁻³
0 restraints	Δρ_min = −0.21 e Å⁻³

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²)

	x	y	z	U_iso*/U_eq
O3	0.48386 (8)	0.25613 (8)	0.57288 (12)	0.0379 (3)
C5	0.41043 (11)	0.21569 (11)	0.48692 (17)	0.0310 (4)
Na1	0.04274 (5)	0.08063 (4)	0.43441 (7)	0.0385 (2)
O1	0.10965 (9)	0.08373 (8)	0.27653 (13)	0.0411 (3)
O2	0.22662 (9)	0.13103 (9)	0.23128 (12)	0.0416 (3)
H2	0.2806	0.1544	0.2746	0.062*
O4	0.38682 (9)	0.20490 (9)	0.35643 (12)	0.0417 (3)
N2	0.36555 (10)	0.18188 (9)	0.67516 (14)	0.0321 (3)
H2A	0.4177	0.2046	0.7425	0.039*
O5	−0.06348 (10)	0.07199 (8)	0.54055 (14)	0.0437 (3)
H5A	−0.0517	0.1150	0.5978	0.052*
H5B	−0.1209	0.0894	0.4662	0.052*
N1	0.22111 (10)	0.11704 (9)	0.56488 (14)	0.0329 (3)
C2	0.34437 (11)	0.17694 (10)	0.53667 (16)	0.0290 (4)
C4	0.19168 (12)	0.11485 (11)	0.31776 (17)	0.0313 (4)
C1	0.25389 (11)	0.13611 (10)	0.46930 (16)	0.0292 (4)
C3	0.29110 (12)	0.14524 (11)	0.68890 (18)	0.0338 (4)
C6	0.29259 (14)	0.13640 (14)	0.82798 (19)	0.0454 (5)
H6A	0.2276	0.1191	0.8121	0.054*
H6B	0.3074	0.1922	0.8748	0.054*
C7	0.36813 (17)	0.07062 (14)	0.9247 (2)	0.0525 (5)
H7A	0.3512	0.0141	0.8804	0.063*
H7B	0.4327	0.0861	0.9367	0.063*
C8	0.3727 (2)	0.06594 (17)	1.0677 (2)	0.0757 (8)
H8A	0.3924	0.1210	1.1138	0.113*
H8B	0.4198	0.0228	1.1242	0.113*
H8C	0.3089	0.0510	1.0564	0.113*
O6	0.0000	0.20200 (12)	0.7500	0.0512 (5)
H6C	0.0310	0.2400	0.7245	0.061*

Atomic displacement parameters (Å²)

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O3	0.0294 (6)	0.0443 (7)	0.0345 (7)	−0.0048 (5)	0.0108 (5)	0.0028 (5)
C5	0.0256 (8)	0.0338 (9)	0.0317 (9)	0.0040 (7)	0.0121 (7)	0.0032 (7)
Na1	0.0328 (4)	0.0462 (4)	0.0354 (4)	−0.0046 (3)	0.0154 (3)	0.0024 (3)
O1	0.0309 (7)	0.0564 (8)	0.0319 (7)	−0.0082 (6)	0.0115 (5)	−0.0032 (5)
O2	0.0347 (7)	0.0600 (8)	0.0289 (6)	−0.0111 (6)	0.0142 (5)	−0.0073 (6)
O4	0.0391 (7)	0.0574 (8)	0.0332 (7)	−0.0083 (6)	0.0209 (6)	−0.0025 (5)
N2	0.0269 (7)	0.0400 (8)	0.0254 (7)	−0.0013 (6)	0.0091 (5)	−0.0007 (6)
O5	0.0472 (8)	0.0453 (8)	0.0372 (7)	0.0025 (6)	0.0190 (6)	0.0020 (5)
N1	0.0298 (7)	0.0401 (8)	0.0291 (7)	−0.0001 (6)	0.0142 (6)	0.0024 (6)
C2	0.0288 (8)	0.0305 (8)	0.0266 (8)	0.0032 (7)	0.0122 (7)	0.0004 (6)
C4	0.0299 (9)	0.0346 (9)	0.0280 (9)	0.0012 (7)	0.0126 (7)	0.0000 (7)
C1	0.0270 (8)	0.0319 (9)	0.0282 (9)	0.0030 (6)	0.0127 (7)	0.0017 (6)
C3	0.0299 (9)	0.0408 (10)	0.0294 (9)	0.0031 (7)	0.0131 (7)	0.0034 (7)
C6	0.0457 (11)	0.0611 (12)	0.0319 (10)	−0.0014 (9)	0.0205 (8)	0.0018 (9)
C7	0.0587 (13)	0.0574 (13)	0.0383 (11)	−0.0110 (10)	0.0205 (9)	0.0054 (9)
C8	0.104 (2)	0.0765 (17)	0.0368 (12)	−0.0225 (15)	0.0254 (13)	0.0041 (11)
O6	0.0693 (13)	0.0439 (11)	0.0553 (12)	0.000	0.0417 (11)	0.000

Geometric parameters (Å, °)

O3—C5	1.237 (2)	O5—H5A	0.8645
C5—O4	1.280 (2)	O5—H5B	0.9066
C5—C2	1.482 (2)	N1—C3	1.327 (2)
Na1—O1	2.3658 (15)	N1—C1	1.374 (2)
Na1—O1ⁱ	2.3644 (14)	C2—C1	1.381 (2)
Na1—O3ⁱⁱ	2.5550 (15)	C4—C1	1.480 (2)
Na1—O5	2.4011 (15)	C3—C6	1.488 (2)
Na1—O5ⁱⁱⁱ	2.3818 (16)	C6—C7	1.524 (3)
Na1—N1	2.4848 (16)	C6—H6A	0.9700
Na1—Na1ⁱⁱⁱ	3.4217 (14)	C6—H6B	0.9700
Na1—Na1ⁱ	3.5291 (16)	C7—C8	1.504 (3)
O1—C4	1.222 (2)	C7—H7A	0.9700
O2—C4	1.300 (2)	C7—H7B	0.9700
O2—H2	0.8200	C8—H8A	0.9600
N2—C3	1.349 (2)	C8—H8B	0.9600
N2—C2	1.364 (2)	C8—H8C	0.9600
N2—H2A	0.8600	O6—H6C	0.8790

C5—O3—Na1ⁱⁱ	113.64 (10)	Na1ⁱⁱⁱ—O5—Na1	91.35 (5)
O3—C5—O4	124.46 (15)	Na1ⁱⁱⁱ—O5—H5A	135.4
O3—C5—C2	118.49 (15)	Na1—O5—H5A	109.5
O4—C5—C2	117.05 (14)	Na1ⁱⁱⁱ—O5—H5B	114.6
O1ⁱ—Na1—O1	83.45 (5)	Na1—O5—H5B	99.5
O1ⁱ—Na1—O5ⁱⁱⁱ	98.46 (5)	H5A—O5—H5B	100.6
O1—Na1—O5ⁱⁱⁱ	91.16 (5)	C3—N1—C1	105.47 (14)
O1ⁱ—Na1—O5	82.24 (5)	C3—N1—Na1	142.55 (12)
O1—Na1—O5	165.50 (5)	C1—N1—Na1	109.17 (10)
O5ⁱⁱⁱ—Na1—O5	88.65 (5)	N2—C2—C1	104.80 (14)
O1ⁱ—Na1—N1	149.80 (6)	N2—C2—C5	121.35 (14)
O1—Na1—N1	69.97 (5)	C1—C2—C5	133.75 (15)
O5ⁱⁱⁱ—Na1—N1	96.21 (5)	O1—C4—O2	121.69 (15)
O5—Na1—N1	124.46 (6)	O1—C4—C1	120.25 (15)
O1ⁱ—Na1—O3ⁱⁱ	83.03 (5)	O2—C4—C1	118.06 (14)
O1—Na1—O3ⁱⁱ	94.36 (5)	N1—C1—C2	110.18 (14)
O5ⁱⁱⁱ—Na1—O3ⁱⁱ	174.41 (5)	N1—C1—C4	119.81 (14)
O5—Na1—O3ⁱⁱ	86.22 (5)	C2—C1—C4	129.97 (15)
N1—Na1—O3ⁱⁱ	84.91 (5)	N1—C3—N2	110.88 (15)
O1ⁱ—Na1—Na1ⁱⁱⁱ	90.44 (4)	N1—C3—C6	126.43 (16)
O1—Na1—Na1ⁱⁱⁱ	133.90 (5)	N2—C3—C6	122.65 (15)
O5ⁱⁱⁱ—Na1—Na1ⁱⁱⁱ	44.55 (4)	C3—C6—C7	112.82 (16)
O5—Na1—Na1ⁱⁱⁱ	44.10 (4)	C3—C6—H6A	109.0
N1—Na1—Na1ⁱⁱⁱ	118.18 (5)	C7—C6—H6A	109.0
O3ⁱⁱ—Na1—Na1ⁱⁱⁱ	130.28 (5)	C3—C6—H6B	109.0
O1ⁱ—Na1—Na1ⁱ	41.76 (4)	C7—C6—H6B	109.0
O1—Na1—Na1ⁱ	41.73 (3)	H6A—C6—H6B	107.8
O5ⁱⁱⁱ—Na1—Na1ⁱ	94.88 (4)	C8—C7—C6	112.2 (2)
O5—Na1—Na1ⁱ	123.85 (5)	C8—C7—H7A	109.2
N1—Na1—Na1ⁱ	110.83 (4)	C6—C7—H7A	109.2
O3ⁱⁱ—Na1—Na1ⁱ	89.81 (3)	C8—C7—H7B	109.2
Na1ⁱⁱⁱ—Na1—Na1ⁱ	116.76 (3)	C6—C7—H7B	109.2
C4—O1—Na1ⁱ	137.76 (11)	H7A—C7—H7B	107.9
C4—O1—Na1	118.44 (11)	C7—C8—H8A	109.5
Na1ⁱ—O1—Na1	96.50 (5)	C7—C8—H8B	109.5
C4—O2—H2	109.5	H8A—C8—H8B	109.5
C3—N2—C2	108.66 (14)	C7—C8—H8C	109.5
C3—N2—H2A	125.7	H8A—C8—H8C	109.5
C2—N2—H2A	125.7	H8B—C8—H8C	109.5

Na1ⁱⁱ—O3—C5—O4	83.19 (17)	Na1ⁱⁱⁱ—Na1—N1—C1	142.32 (10)
Na1ⁱⁱ—O3—C5—C2	−96.58 (14)	Na1ⁱ—Na1—N1—C1	3.70 (11)
O1ⁱ—Na1—O1—C4	153.03 (11)	C3—N2—C2—C1	0.27 (17)
O5ⁱⁱⁱ—Na1—O1—C4	−108.59 (13)	C3—N2—C2—C5	177.03 (14)
O5—Na1—O1—C4	162.3 (2)	O3—C5—C2—N2	−3.0 (2)
N1—Na1—O1—C4	−12.40 (12)	O4—C5—C2—N2	177.24 (15)
O3ⁱⁱ—Na1—O1—C4	70.56 (13)	O3—C5—C2—C1	172.70 (17)
Na1ⁱⁱⁱ—Na1—O1—C4	−122.69 (12)	O4—C5—C2—C1	−7.1 (3)
Na1ⁱ—Na1—O1—C4	155.37 (15)	Na1ⁱ—O1—C4—O2	−27.1 (3)
O1ⁱ—Na1—O1—Na1ⁱ	−2.35 (7)	Na1—O1—C4—O2	−169.10 (12)
O5ⁱⁱⁱ—Na1—O1—Na1ⁱ	96.04 (5)	Na1ⁱ—O1—C4—C1	152.23 (13)
O5—Na1—O1—Na1ⁱ	7.0 (2)	Na1—O1—C4—C1	10.2 (2)
N1—Na1—O1—Na1ⁱ	−167.77 (6)	C3—N1—C1—C2	−0.50 (19)
O3ⁱⁱ—Na1—O1—Na1ⁱ	−84.81 (5)	Na1—N1—C1—C2	165.02 (11)
Na1ⁱⁱⁱ—Na1—O1—Na1ⁱ	81.93 (7)	C3—N1—C1—C4	−178.63 (15)
O1ⁱ—Na1—O5—Na1ⁱⁱⁱ	98.73 (5)	Na1—N1—C1—C4	−13.10 (18)
O1—Na1—O5—Na1ⁱⁱⁱ	89.4 (2)	N2—C2—C1—N1	0.15 (18)
O5ⁱⁱⁱ—Na1—O5—Na1ⁱⁱⁱ	0.0	C5—C2—C1—N1	−176.03 (16)
N1—Na1—O5—Na1ⁱⁱⁱ	−96.60 (7)	N2—C2—C1—C4	178.02 (16)
O3ⁱⁱ—Na1—O5—Na1ⁱⁱⁱ	−177.79 (5)	C5—C2—C1—C4	1.8 (3)
Na1ⁱ—Na1—O5—Na1ⁱⁱⁱ	94.97 (4)	O1—C4—C1—N1	3.0 (2)
O1ⁱ—Na1—N1—C3	139.23 (18)	O2—C4—C1—N1	−177.59 (15)
O1—Na1—N1—C3	169.0 (2)	O1—C4—C1—C2	−174.66 (17)
O5ⁱⁱⁱ—Na1—N1—C3	−102.0 (2)	O2—C4—C1—C2	4.7 (3)
O5—Na1—N1—C3	−9.4 (2)	C1—N1—C3—N2	0.68 (19)
O3ⁱⁱ—Na1—N1—C3	72.5 (2)	Na1—N1—C3—N2	−156.48 (14)
Na1ⁱⁱⁱ—Na1—N1—C3	−61.0 (2)	C1—N1—C3—C6	−177.21 (17)
Na1ⁱ—Na1—N1—C3	160.36 (18)	Na1—N1—C3—C6	25.6 (3)
O1ⁱ—Na1—N1—C1	−17.43 (17)	C2—N2—C3—N1	−0.61 (19)
O1—Na1—N1—C1	12.38 (10)	C2—N2—C3—C6	177.38 (16)
O5ⁱⁱⁱ—Na1—N1—C1	101.34 (11)	N1—C3—C6—C7	107.8 (2)
O5—Na1—N1—C1	−166.03 (10)	N2—C3—C6—C7	−69.8 (2)
O3ⁱⁱ—Na1—N1—C1	−84.16 (11)	C3—C6—C7—C8	176.85 (18)

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

Hydrogen-bond geometry (Å, °)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···O3^iv	0.86	2.00	2.8384 (18)	164
O2—H2···O4	0.82	1.64	2.4603 (18)	178
O5—H5B···O2ⁱ	0.91	2.07	2.9493 (18)	164
O5—H5A···O6	0.86	1.97	2.8234 (19)	169
O6—H6C···O4ⁱⁱ	0.88	2.03	2.8835 (16)	163

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

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HY2402).

References

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