metal-organic compounds
Poly[[μ2-aqua-μ3-(4-carboxy-2-propyl-1H-imidazole-5-carboxylato-κ4N3,O4:O4:O5)-sodium] hemihydrate]
aDepartment of Chemistry, Guangxi University for Nationalities, Nanning 530006, People's Republic of China
*Correspondence e-mail: huangzhongjing1@yahoo.com.cn
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).
Experimental
Crystal data
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Refinement
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Data collection: SMART (Bruker, 2007); cell 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).
Supporting information
10.1107/S1600536811007732/hy2402sup1.cif
contains datablocks I, global. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536811007732/hy2402Isup2.hkl
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).
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).
Data collection: SMART (Bruker, 2007); cell
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: DIAMOND (Brandenburg, 1999); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).[Na(C8H9N2O4)(H2O)]·0.5H2O | F(000) = 1032 |
Mr = 247.18 | Dx = 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 |
Bruker APEX CCD diffractometer | 1986 independent reflections |
Radiation source: fine-focus sealed tube | 1669 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.020 |
ϕ and ω scans | θmax = 25.0°, θmin = 2.0° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −18→17 |
Tmin = 0.528, Tmax = 0.562 | k = −18→17 |
5971 measured reflections | l = −11→12 |
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(Fo2) + (0.0609P)2 + 0.6897P] where P = (Fo2 + 2Fc2)/3 |
1986 reflections | (Δ/σ)max < 0.001 |
152 parameters | Δρmax = 0.23 e Å−3 |
0 restraints | Δρmin = −0.21 e Å−3 |
[Na(C8H9N2O4)(H2O)]·0.5H2O | V = 2252.4 (9) Å3 |
Mr = 247.18 | Z = 8 |
Monoclinic, C2/c | Mo Kα radiation |
a = 15.406 (4) Å | µ = 0.15 mm−1 |
b = 15.478 (4) Å | T = 296 K |
c = 10.734 (3) Å | 0.52 × 0.47 × 0.44 mm |
β = 118.364 (3)° |
Bruker APEX CCD diffractometer | 1986 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | 1669 reflections with I > 2σ(I) |
Tmin = 0.528, Tmax = 0.562 | Rint = 0.020 |
5971 measured reflections |
R[F2 > 2σ(F2)] = 0.034 | 0 restraints |
wR(F2) = 0.106 | H-atom parameters constrained |
S = 1.10 | Δρmax = 0.23 e Å−3 |
1986 reflections | Δρmin = −0.21 e Å−3 |
152 parameters |
x | y | z | Uiso*/Ueq | ||
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* |
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 |
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. |
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H2A···O3iv | 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: (i) −x, y, −z+1/2; (ii) −x+1/2, −y+1/2, −z+1; (iv) −x+1, y, −z+3/2. |
Experimental details
Crystal data | |
Chemical formula | [Na(C8H9N2O4)(H2O)]·0.5H2O |
Mr | 247.18 |
Crystal system, space group | Monoclinic, C2/c |
Temperature (K) | 296 |
a, b, c (Å) | 15.406 (4), 15.478 (4), 10.734 (3) |
β (°) | 118.364 (3) |
V (Å3) | 2252.4 (9) |
Z | 8 |
Radiation type | Mo Kα |
µ (mm−1) | 0.15 |
Crystal size (mm) | 0.52 × 0.47 × 0.44 |
Data collection | |
Diffractometer | Bruker APEX CCD diffractometer |
Absorption correction | Multi-scan (SADABS; Sheldrick, 1996) |
Tmin, Tmax | 0.528, 0.562 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 5971, 1986, 1669 |
Rint | 0.020 |
(sin θ/λ)max (Å−1) | 0.595 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.034, 0.106, 1.10 |
No. of reflections | 1986 |
No. of parameters | 152 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.23, −0.21 |
Computer programs: SMART (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), DIAMOND (Brandenburg, 1999), SHELXTL (Sheldrick, 2008).
Na1—O1 | 2.3658 (15) | Na1—O5 | 2.4011 (15) |
Na1—O1i | 2.3644 (14) | Na1—O5iii | 2.3818 (16) |
Na1—O3ii | 2.5550 (15) | Na1—N1 | 2.4848 (16) |
Symmetry codes: (i) −x, y, −z+1/2; (ii) −x+1/2, −y+1/2, −z+1; (iii) −x, −y, −z+1. |
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H2A···O3iv | 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: (i) −x, y, −z+1/2; (ii) −x+1/2, −y+1/2, −z+1; (iv) −x+1, y, −z+3/2. |
Acknowledgements
This work was supported by the Innovation Project of Guangxi University for Nationalities (gxun-chx2010083).
References
Baures, P. W. (1999). Org. Lett. 1, 249–252. Web of Science CrossRef PubMed CAS Google Scholar
Bogdanova, N. A., Kulikova, O. G. & Borodkin, Y. S. (1992). Bull. Exp. Biol. Med. 111, 159–161. Google Scholar
Borodkin, Y. S., Shabanov, P. D., Lapina, I. A. & Yaitchnikov, I. K. (1984). Act. Nerv. Sup. 26, 97–102. CAS Google Scholar
Brandenburg, K. (1999). DIAMOND. Crystal Impact GbR, Bonn, Germany. Google Scholar
Bruker (2007). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Reichardt, B. A., Belyavtseva, L. M. & Kulikova, O. G. (1992). Bull. Exp. Biol. Med. 113, 506–508. Google Scholar
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Su, C.-Y., Cai, Y.-P., Chen, C.-L. & Kang, B.-S. (2001). Inorg. Chem. 40, 2210–2211. Web of Science CSD CrossRef PubMed CAS Google Scholar
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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).