Poly[[μ(2)-aqua-μ(3)-(4-carb-oxy-2-propyl-1H-imidazole-5-carboxyl-ato-κN,O:O:O)-sodium] hemihydrate].

In the title compound, {[Na(C(8)H(9)N(2)O(4))(H(2)O)]·0.5H(2)O}(n), the Na(+) ion is coordinated by two bridging water mol-ecules, one N atom and three O atoms from three 4-carb-oxy-2-propyl-1H-imidazole-5-carboxyl-ate (H(2)pimdc) ligands. Adjacent Na(+) ions are linked alternately by two water O atoms and two carb-oxy O atoms into a chain along [001]. These chains are connected through the coordination of the carboxyl-ate O atoms to the Na(+) ions, forming a three-dimensional structure. An intra-molecular O-H⋯O hydrogen bond and inter-molecular 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

[Na(C8H9N2O4)(H2O)]·0.5H2O

M = 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

Δρmax = 0.23 e Å−3

Δρmin = −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 ▶).

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

[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	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

	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)

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

Table 1

Selected bond lengths (Å)

Na1—O1	2.3658 (15)
Na1—O1i	2.3644 (14)
Na1—O3ii	2.5550 (15)
Na1—O5	2.4011 (15)
Na1—O5iii	2.3818 (16)
Na1—N1	2.4848 (16)

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

Table 2

Hydrogen-bond geometry (Å, °)

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) ; (ii) ; (iv) .