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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]

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 [triangle]); Bogdanova et al. (1992 [triangle]); Borodkin et al. (1984 [triangle]); Reichardt et al. (1992 [triangle]); Su et al. (2001 [triangle]).

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

Experimental

Crystal data

  • [Na(C8H9N2O4)(H2O)]·0.5H2O
  • M r = 247.18
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-67-0m408-efi1.jpg
  • 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 [triangle]) 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
  • Δρmax = 0.23 e Å−3
  • Δρmin = −0.21 e Å−3

Data collection: SMART (Bruker, 2007 [triangle]); cell refinement: SAINT (Bruker, 2007 [triangle]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: DIAMOND (Brandenburg, 1999 [triangle]); software used to prepare material for publication: SHELXTL (Sheldrick, 2008 [triangle]).

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

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

Refinement

H atoms except those of water molecules were positioned geometrically and refined using a riding model, with C—H = 0.97 (CH2) and 0.96 (CH3), N—H = 0.86 and O—H = 0.82 Å and with Uiso(H) = 1.2(1.5 for methyl)Ueq(C,N,O). H atoms of water molecules were located in a difference Fourier map and refined as riding atoms, with Uiso(H) = 1.2Ueq(O).

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)]·0.5H2OF(000) = 1032
Mr = 247.18Dx = 1.458 Mg m3
Monoclinic, C2/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2ycCell parameters from 2142 reflections
a = 15.406 (4) Åθ = 2.4–26.8°
b = 15.478 (4) ŵ = 0.15 mm1
c = 10.734 (3) ÅT = 296 K
β = 118.364 (3)°Block, colorless
V = 2252.4 (9) Å30.52 × 0.47 × 0.44 mm
Z = 8

Data collection

Bruker APEX CCD diffractometer1986 independent reflections
Radiation source: fine-focus sealed tube1669 reflections with I > 2σ(I)
graphiteRint = 0.020
[var phi] and ω scansθmax = 25.0°, θmin = 2.0°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)h = −18→17
Tmin = 0.528, Tmax = 0.562k = −18→17
5971 measured reflectionsl = −11→12

Refinement

Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.034Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.106H-atom parameters constrained
S = 1.10w = 1/[σ2(Fo2) + (0.0609P)2 + 0.6897P] where P = (Fo2 + 2Fc2)/3
1986 reflections(Δ/σ)max < 0.001
152 parametersΔρmax = 0.23 e Å3
0 restraintsΔρmin = −0.21 e Å3

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

xyzUiso*/Ueq
O30.48386 (8)0.25613 (8)0.57288 (12)0.0379 (3)
C50.41043 (11)0.21569 (11)0.48692 (17)0.0310 (4)
Na10.04274 (5)0.08063 (4)0.43441 (7)0.0385 (2)
O10.10965 (9)0.08373 (8)0.27653 (13)0.0411 (3)
O20.22662 (9)0.13103 (9)0.23128 (12)0.0416 (3)
H20.28060.15440.27460.062*
O40.38682 (9)0.20490 (9)0.35643 (12)0.0417 (3)
N20.36555 (10)0.18188 (9)0.67516 (14)0.0321 (3)
H2A0.41770.20460.74250.039*
O5−0.06348 (10)0.07199 (8)0.54055 (14)0.0437 (3)
H5A−0.05170.11500.59780.052*
H5B−0.12090.08940.46620.052*
N10.22111 (10)0.11704 (9)0.56488 (14)0.0329 (3)
C20.34437 (11)0.17694 (10)0.53667 (16)0.0290 (4)
C40.19168 (12)0.11485 (11)0.31776 (17)0.0313 (4)
C10.25389 (11)0.13611 (10)0.46930 (16)0.0292 (4)
C30.29110 (12)0.14524 (11)0.68890 (18)0.0338 (4)
C60.29259 (14)0.13640 (14)0.82798 (19)0.0454 (5)
H6A0.22760.11910.81210.054*
H6B0.30740.19220.87480.054*
C70.36813 (17)0.07062 (14)0.9247 (2)0.0525 (5)
H7A0.35120.01410.88040.063*
H7B0.43270.08610.93670.063*
C80.3727 (2)0.06594 (17)1.0677 (2)0.0757 (8)
H8A0.39240.12101.11380.113*
H8B0.41980.02281.12420.113*
H8C0.30890.05101.05640.113*
O60.00000.20200 (12)0.75000.0512 (5)
H6C0.03100.24000.72450.061*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
O30.0294 (6)0.0443 (7)0.0345 (7)−0.0048 (5)0.0108 (5)0.0028 (5)
C50.0256 (8)0.0338 (9)0.0317 (9)0.0040 (7)0.0121 (7)0.0032 (7)
Na10.0328 (4)0.0462 (4)0.0354 (4)−0.0046 (3)0.0154 (3)0.0024 (3)
O10.0309 (7)0.0564 (8)0.0319 (7)−0.0082 (6)0.0115 (5)−0.0032 (5)
O20.0347 (7)0.0600 (8)0.0289 (6)−0.0111 (6)0.0142 (5)−0.0073 (6)
O40.0391 (7)0.0574 (8)0.0332 (7)−0.0083 (6)0.0209 (6)−0.0025 (5)
N20.0269 (7)0.0400 (8)0.0254 (7)−0.0013 (6)0.0091 (5)−0.0007 (6)
O50.0472 (8)0.0453 (8)0.0372 (7)0.0025 (6)0.0190 (6)0.0020 (5)
N10.0298 (7)0.0401 (8)0.0291 (7)−0.0001 (6)0.0142 (6)0.0024 (6)
C20.0288 (8)0.0305 (8)0.0266 (8)0.0032 (7)0.0122 (7)0.0004 (6)
C40.0299 (9)0.0346 (9)0.0280 (9)0.0012 (7)0.0126 (7)0.0000 (7)
C10.0270 (8)0.0319 (9)0.0282 (9)0.0030 (6)0.0127 (7)0.0017 (6)
C30.0299 (9)0.0408 (10)0.0294 (9)0.0031 (7)0.0131 (7)0.0034 (7)
C60.0457 (11)0.0611 (12)0.0319 (10)−0.0014 (9)0.0205 (8)0.0018 (9)
C70.0587 (13)0.0574 (13)0.0383 (11)−0.0110 (10)0.0205 (9)0.0054 (9)
C80.104 (2)0.0765 (17)0.0368 (12)−0.0225 (15)0.0254 (13)0.0041 (11)
O60.0693 (13)0.0439 (11)0.0553 (12)0.0000.0417 (11)0.000

Geometric parameters (Å, °)

O3—C51.237 (2)O5—H5A0.8645
C5—O41.280 (2)O5—H5B0.9066
C5—C21.482 (2)N1—C31.327 (2)
Na1—O12.3658 (15)N1—C11.374 (2)
Na1—O1i2.3644 (14)C2—C11.381 (2)
Na1—O3ii2.5550 (15)C4—C11.480 (2)
Na1—O52.4011 (15)C3—C61.488 (2)
Na1—O5iii2.3818 (16)C6—C71.524 (3)
Na1—N12.4848 (16)C6—H6A0.9700
Na1—Na1iii3.4217 (14)C6—H6B0.9700
Na1—Na1i3.5291 (16)C7—C81.504 (3)
O1—C41.222 (2)C7—H7A0.9700
O2—C41.300 (2)C7—H7B0.9700
O2—H20.8200C8—H8A0.9600
N2—C31.349 (2)C8—H8B0.9600
N2—C21.364 (2)C8—H8C0.9600
N2—H2A0.8600O6—H6C0.8790
C5—O3—Na1ii113.64 (10)Na1iii—O5—Na191.35 (5)
O3—C5—O4124.46 (15)Na1iii—O5—H5A135.4
O3—C5—C2118.49 (15)Na1—O5—H5A109.5
O4—C5—C2117.05 (14)Na1iii—O5—H5B114.6
O1i—Na1—O183.45 (5)Na1—O5—H5B99.5
O1i—Na1—O5iii98.46 (5)H5A—O5—H5B100.6
O1—Na1—O5iii91.16 (5)C3—N1—C1105.47 (14)
O1i—Na1—O582.24 (5)C3—N1—Na1142.55 (12)
O1—Na1—O5165.50 (5)C1—N1—Na1109.17 (10)
O5iii—Na1—O588.65 (5)N2—C2—C1104.80 (14)
O1i—Na1—N1149.80 (6)N2—C2—C5121.35 (14)
O1—Na1—N169.97 (5)C1—C2—C5133.75 (15)
O5iii—Na1—N196.21 (5)O1—C4—O2121.69 (15)
O5—Na1—N1124.46 (6)O1—C4—C1120.25 (15)
O1i—Na1—O3ii83.03 (5)O2—C4—C1118.06 (14)
O1—Na1—O3ii94.36 (5)N1—C1—C2110.18 (14)
O5iii—Na1—O3ii174.41 (5)N1—C1—C4119.81 (14)
O5—Na1—O3ii86.22 (5)C2—C1—C4129.97 (15)
N1—Na1—O3ii84.91 (5)N1—C3—N2110.88 (15)
O1i—Na1—Na1iii90.44 (4)N1—C3—C6126.43 (16)
O1—Na1—Na1iii133.90 (5)N2—C3—C6122.65 (15)
O5iii—Na1—Na1iii44.55 (4)C3—C6—C7112.82 (16)
O5—Na1—Na1iii44.10 (4)C3—C6—H6A109.0
N1—Na1—Na1iii118.18 (5)C7—C6—H6A109.0
O3ii—Na1—Na1iii130.28 (5)C3—C6—H6B109.0
O1i—Na1—Na1i41.76 (4)C7—C6—H6B109.0
O1—Na1—Na1i41.73 (3)H6A—C6—H6B107.8
O5iii—Na1—Na1i94.88 (4)C8—C7—C6112.2 (2)
O5—Na1—Na1i123.85 (5)C8—C7—H7A109.2
N1—Na1—Na1i110.83 (4)C6—C7—H7A109.2
O3ii—Na1—Na1i89.81 (3)C8—C7—H7B109.2
Na1iii—Na1—Na1i116.76 (3)C6—C7—H7B109.2
C4—O1—Na1i137.76 (11)H7A—C7—H7B107.9
C4—O1—Na1118.44 (11)C7—C8—H8A109.5
Na1i—O1—Na196.50 (5)C7—C8—H8B109.5
C4—O2—H2109.5H8A—C8—H8B109.5
C3—N2—C2108.66 (14)C7—C8—H8C109.5
C3—N2—H2A125.7H8A—C8—H8C109.5
C2—N2—H2A125.7H8B—C8—H8C109.5
Na1ii—O3—C5—O483.19 (17)Na1iii—Na1—N1—C1142.32 (10)
Na1ii—O3—C5—C2−96.58 (14)Na1i—Na1—N1—C13.70 (11)
O1i—Na1—O1—C4153.03 (11)C3—N2—C2—C10.27 (17)
O5iii—Na1—O1—C4−108.59 (13)C3—N2—C2—C5177.03 (14)
O5—Na1—O1—C4162.3 (2)O3—C5—C2—N2−3.0 (2)
N1—Na1—O1—C4−12.40 (12)O4—C5—C2—N2177.24 (15)
O3ii—Na1—O1—C470.56 (13)O3—C5—C2—C1172.70 (17)
Na1iii—Na1—O1—C4−122.69 (12)O4—C5—C2—C1−7.1 (3)
Na1i—Na1—O1—C4155.37 (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—Na1i96.04 (5)Na1i—O1—C4—C1152.23 (13)
O5—Na1—O1—Na1i7.0 (2)Na1—O1—C4—C110.2 (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—C2165.02 (11)
Na1iii—Na1—O1—Na1i81.93 (7)C3—N1—C1—C4−178.63 (15)
O1i—Na1—O5—Na1iii98.73 (5)Na1—N1—C1—C4−13.10 (18)
O1—Na1—O5—Na1iii89.4 (2)N2—C2—C1—N10.15 (18)
O5iii—Na1—O5—Na1iii0.0C5—C2—C1—N1−176.03 (16)
N1—Na1—O5—Na1iii−96.60 (7)N2—C2—C1—C4178.02 (16)
O3ii—Na1—O5—Na1iii−177.79 (5)C5—C2—C1—C41.8 (3)
Na1i—Na1—O5—Na1iii94.97 (4)O1—C4—C1—N13.0 (2)
O1i—Na1—N1—C3139.23 (18)O2—C4—C1—N1−177.59 (15)
O1—Na1—N1—C3169.0 (2)O1—C4—C1—C2−174.66 (17)
O5iii—Na1—N1—C3−102.0 (2)O2—C4—C1—C24.7 (3)
O5—Na1—N1—C3−9.4 (2)C1—N1—C3—N20.68 (19)
O3ii—Na1—N1—C372.5 (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—C3160.36 (18)Na1—N1—C3—C625.6 (3)
O1i—Na1—N1—C1−17.43 (17)C2—N2—C3—N1−0.61 (19)
O1—Na1—N1—C112.38 (10)C2—N2—C3—C6177.38 (16)
O5iii—Na1—N1—C1101.34 (11)N1—C3—C6—C7107.8 (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—C8176.85 (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···AD—HH···AD···AD—H···A
N2—H2A···O3iv0.862.002.8384 (18)164
O2—H2···O40.821.642.4603 (18)178
O5—H5B···O2i0.912.072.9493 (18)164
O5—H5A···O60.861.972.8234 (19)169
O6—H6C···O4ii0.882.032.8835 (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

  • Baures, P. W. (1999). Org. Lett. 1, 249–252. [PubMed]
  • Bogdanova, N. A., Kulikova, O. G. & Borodkin, Y. S. (1992). Bull. Exp. Biol. Med. 111, 159–161.
  • Borodkin, Y. S., Shabanov, P. D., Lapina, I. A. & Yaitchnikov, I. K. (1984). Act. Nerv. Sup. 26, 97–102.
  • Brandenburg, K. (1999). DIAMONDCrystal Impact GbR, Bonn, Germany.
  • Bruker (2007). SMART and SAINTBruker AXS Inc., Madison, Wisconsin, USA.
  • Reichardt, B. A., Belyavtseva, L. M. & Kulikova, O. G. (1992). Bull. Exp. Biol. Med. 113, 506–508.
  • Sheldrick, G. M. (1996). SADABSUniversity of Göttingen, Germany.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Su, C.-Y., Cai, Y.-P., Chen, C.-L. & Kang, B.-S. (2001). Inorg. Chem. 40, 2210–2211. [PubMed]

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