Poly[diaqua-bis(μ-4-carb-oxy-2-propyl-1H-imidazole-5-carboxyl-ato-κN,O:O)calcium(II)].

In the title complex, [Ca(C(8)H(9)N(2)O(4))(2)(H(2)O)(2)](n), the Ca(II) atom is eight-coordinated in a distorted square-anti-prismatic environment. The water-coordinated Ca atom is N,O-chelated by the monocarboxyl-ate anion; the carboxyl -CO(2) portion engaged in chelation bears an acid hydrogen. The free -CO(2) portion engages in bonding to adjacent Ca atoms. The Ca(II) centres are connected through the ligand, forming a layer structure; the layers are linked by hydrogen bonds into a three-dimensional network.

Related literature

For the potential uses and diverse structrual types of structures containing metals and n class="Disease">N-heterocyclic carboxylic acids, see: Liang et al. (2002 ▶); Net et al. (1989 ▶); Nie et al. (2007 ▶).

Experimental

Crystal data

[Ca(C8H9N2O4)2(H2O)2]

M = 470.46

Monoclinic,

a = 12.703 (3) Å

b = 13.006 (3) Å

c = 11.697 (2) Å

β = 97.864 (2)°

V = 1914.3 (7) Å3

Z = 4

Mo Kα radiation

μ = 0.40 mm−1

T = 273 K

0.32 × 0.24 × 0.20 mm

Data collection

Bruker APEXII area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2004 ▶) T min = 0.884, T max = 0.925

4830 measured reflections

1718 independent reflections

1504 reflections with I > 2σ(I)

R int = 0.040

Refinement

R[F 2 > 2σ(F 2)] = 0.034

wR(F 2) = 0.099

S = 1.02

1718 reflections

144 parameters

3 restraints

H-atom parameters constrained

Δρmax = 0.29 e Å−3

Δρmin = −0.23 e Å−3

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: SAINT (Bruker, 2004 ▶); data reduction: SAIn class="Chemical">NT; 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.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809052799/ng2702sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809052799/ng2702Isup2.hkl

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

[Ca(C8H9N2O4)2(H2O)2]	F(000) = 984
Mr = 470.46	Dx = 1.632 Mg m−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 3600 reflections
a = 12.703 (3) Å	θ = 1.4–28°
b = 13.006 (3) Å	µ = 0.40 mm−1
c = 11.697 (2) Å	T = 273 K
β = 97.864 (2)°	Block, white
V = 1914.3 (7) Å3	0.32 × 0.24 × 0.20 mm
Z = 4

Bruker APEXII area-detector diffractometer	1718 independent reflections
Radiation source: fine-focus sealed tube	1504 reflections with I > 2σ(I)
graphite	Rint = 0.040
φ and ω scan	θmax = 25.2°, θmin = 2.3°
Absorption correction: multi-scan (SADABS; Bruker, 2004)	h = −13→15
Tmin = 0.884, Tmax = 0.925	k = −14→15
4830 measured reflections	l = −14→13

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)] = 0.034	H-atom parameters constrained
wR(F2) = 0.099	w = 1/[σ2(Fo2) + (0.0551P)2 + 1.470P] where P = (Fo2 + 2Fc2)/3
S = 1.01	(Δ/σ)max < 0.001
1718 reflections	Δρmax = 0.29 e Å−3
144 parameters	Δρmin = −0.23 e Å−3
3 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: 0.0076 (9)

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.

	x	y	z	Uiso*/Ueq
Ca1	0.5000	0.07420 (4)	0.2500	0.0189 (2)
O1	0.33875 (11)	0.05035 (10)	0.36313 (12)	0.0262 (3)
O1W	0.55495 (11)	0.10622 (11)	0.45862 (12)	0.0319 (4)
H1W	0.5121	0.1347	0.4970	0.048*
H2W	0.5769	0.0519	0.4904	0.048*
O2	0.20033 (11)	0.11430 (10)	0.43530 (13)	0.0296 (4)
H1	0.1663	0.1680	0.4316	0.044*
O3	0.09452 (11)	0.27478 (11)	0.42169 (12)	0.0308 (4)
O4	0.09469 (12)	0.42512 (10)	0.33195 (13)	0.0352 (4)
N1	0.36595 (12)	0.22589 (11)	0.23987 (13)	0.0201 (4)
N2	0.26433 (12)	0.36382 (11)	0.21921 (13)	0.0225 (4)
H2	0.2403	0.4229	0.1951	0.027*
C1	0.28670 (14)	0.21777 (14)	0.30920 (15)	0.0192 (4)
C2	0.22299 (14)	0.30376 (14)	0.29747 (16)	0.0209 (4)
C3	0.34950 (14)	0.31557 (14)	0.18572 (16)	0.0215 (4)
C4	0.27622 (14)	0.12212 (14)	0.37333 (16)	0.0204 (4)
C5	0.40949 (15)	0.36092 (15)	0.09774 (17)	0.0255 (4)
H5A	0.4753	0.3231	0.0974	0.031*
H5B	0.4277	0.4315	0.1189	0.031*
C6	0.34718 (17)	0.35929 (17)	−0.02384 (18)	0.0334 (5)
H6A	0.3399	0.2888	−0.0508	0.040*
H6B	0.2764	0.3865	−0.0212	0.040*
C7	0.40144 (19)	0.42208 (18)	−0.1082 (2)	0.0382 (6)
H7A	0.4067	0.4924	−0.0832	0.057*
H7B	0.3606	0.4184	−0.1835	0.057*
H7C	0.4714	0.3952	−0.1113	0.057*
C8	0.13058 (15)	0.33836 (15)	0.35251 (16)	0.0240 (4)

	U11	U22	U33	U12	U13	U23
Ca1	0.0189 (3)	0.0157 (3)	0.0229 (3)	0.000	0.0052 (2)	0.000
O1	0.0267 (7)	0.0187 (7)	0.0336 (8)	0.0026 (6)	0.0051 (6)	0.0014 (6)
O1W	0.0345 (8)	0.0327 (8)	0.0299 (8)	0.0035 (6)	0.0095 (6)	0.0011 (6)
O2	0.0303 (8)	0.0228 (7)	0.0384 (8)	0.0041 (6)	0.0140 (7)	0.0073 (6)
O3	0.0295 (8)	0.0300 (8)	0.0360 (8)	0.0045 (6)	0.0155 (6)	0.0036 (6)
O4	0.0385 (9)	0.0295 (8)	0.0394 (9)	0.0182 (6)	0.0119 (7)	0.0052 (6)
N1	0.0188 (8)	0.0190 (8)	0.0231 (8)	0.0000 (6)	0.0049 (6)	0.0001 (6)
N2	0.0250 (8)	0.0157 (8)	0.0275 (9)	0.0045 (6)	0.0059 (7)	0.0042 (6)
C1	0.0185 (9)	0.0192 (9)	0.0198 (9)	−0.0003 (7)	0.0023 (7)	−0.0013 (7)
C2	0.0219 (9)	0.0200 (9)	0.0212 (9)	0.0015 (7)	0.0046 (8)	−0.0011 (7)
C3	0.0207 (9)	0.0201 (9)	0.0236 (10)	−0.0007 (7)	0.0027 (8)	−0.0004 (7)
C4	0.0203 (9)	0.0191 (9)	0.0215 (10)	−0.0007 (7)	0.0020 (7)	−0.0016 (7)
C5	0.0230 (10)	0.0255 (10)	0.0288 (11)	−0.0018 (8)	0.0062 (8)	0.0047 (8)
C6	0.0311 (11)	0.0350 (12)	0.0332 (12)	−0.0093 (9)	0.0012 (9)	0.0059 (9)
C7	0.0419 (13)	0.0429 (13)	0.0294 (12)	−0.0077 (10)	0.0037 (10)	0.0069 (9)
C8	0.0235 (10)	0.0266 (10)	0.0219 (10)	0.0022 (8)	0.0035 (8)	−0.0017 (8)

Ca1—O4i	2.4104 (14)	N1—C1	1.380 (2)
Ca1—O4ii	2.4104 (14)	N2—C3	1.354 (2)
Ca1—O1W	2.4798 (15)	N2—C2	1.362 (2)
Ca1—O1Wiii	2.4799 (15)	N2—H2	0.8600
Ca1—N1iii	2.5982 (15)	C1—C2	1.376 (3)
Ca1—N1	2.5982 (15)	C1—C4	1.468 (3)
Ca1—O1	2.6048 (14)	C2—C8	1.484 (3)
Ca1—O1iii	2.6049 (14)	C3—C5	1.484 (3)
O1—C4	1.242 (2)	C5—C6	1.530 (3)
O1W—H1W	0.8378	C5—H5A	0.9700
O1W—H2W	0.8287	C5—H5B	0.9700
O2—C4	1.287 (2)	C6—C7	1.517 (3)
O2—H1	0.8200	C6—H6A	0.9700
O3—C8	1.284 (2)	C6—H6B	0.9700
O4—C8	1.228 (2)	C7—H7A	0.9600
O4—Ca1iv	2.4102 (14)	C7—H7B	0.9600
N1—C3	1.330 (2)	C7—H7C	0.9600
O4i—Ca1—O4ii	72.89 (8)	C3—N2—C2	108.98 (15)
O4i—Ca1—O1W	125.76 (5)	C3—N2—H2	125.5
O4ii—Ca1—O1W	71.69 (5)	C2—N2—H2	125.5
O4i—Ca1—O1Wiii	71.69 (5)	C2—C1—N1	110.21 (16)
O4ii—Ca1—O1Wiii	125.76 (5)	C2—C1—C4	130.27 (17)
O1W—Ca1—O1Wiii	160.66 (7)	N1—C1—C4	119.30 (15)
O4i—Ca1—N1iii	156.52 (5)	N2—C2—C1	104.93 (16)
O4ii—Ca1—N1iii	107.72 (5)	N2—C2—C8	121.21 (16)
O1W—Ca1—N1iii	74.52 (5)	C1—C2—C8	133.83 (17)
O1Wiii—Ca1—N1iii	90.68 (5)	N1—C3—N2	110.39 (16)
O4i—Ca1—N1	107.72 (5)	N1—C3—C5	128.07 (17)
O4ii—Ca1—N1	156.53 (5)	N2—C3—C5	121.51 (17)
O1W—Ca1—N1	90.68 (5)	O1—C4—O2	122.20 (17)
O1Wiii—Ca1—N1	74.52 (5)	O1—C4—C1	118.94 (16)
N1iii—Ca1—N1	81.19 (7)	O2—C4—C1	118.82 (16)
O4i—Ca1—O1	73.86 (5)	C3—C5—C6	112.93 (16)
O4ii—Ca1—O1	94.96 (5)	C3—C5—H5A	109.0
O1W—Ca1—O1	69.83 (5)	C6—C5—H5A	109.0
O1Wiii—Ca1—O1	112.64 (5)	C3—C5—H5B	109.0
N1iii—Ca1—O1	128.56 (5)	C6—C5—H5B	109.0
N1—Ca1—O1	63.74 (4)	H5A—C5—H5B	107.8
O4i—Ca1—O1iii	94.96 (5)	C7—C6—C5	111.95 (17)
O4ii—Ca1—O1iii	73.85 (5)	C7—C6—H6A	109.2
O1W—Ca1—O1iii	112.64 (5)	C5—C6—H6A	109.2
O1Wiii—Ca1—O1iii	69.82 (5)	C7—C6—H6B	109.2
N1iii—Ca1—O1iii	63.74 (4)	C5—C6—H6B	109.2
N1—Ca1—O1iii	128.56 (5)	H6A—C6—H6B	107.9
O1—Ca1—O1iii	166.32 (6)	C6—C7—H7A	109.5
C4—O1—Ca1	121.13 (12)	C6—C7—H7B	109.5
Ca1—O1W—H1W	119.1	H7A—C7—H7B	109.5
Ca1—O1W—H2W	109.3	C6—C7—H7C	109.5
H1W—O1W—H2W	109.8	H7A—C7—H7C	109.5
C4—O2—H1	109.5	H7B—C7—H7C	109.5
C8—O4—Ca1iv	165.57 (15)	O4—C8—O3	124.05 (18)
C3—N1—C1	105.49 (14)	O4—C8—C2	119.22 (17)
C3—N1—Ca1	138.32 (12)	O3—C8—C2	116.72 (17)
C1—N1—Ca1	116.18 (11)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O1v	0.86	2.01	2.859 (2)	171
O1W—H2W···O1vi	0.83	2.31	3.088 (2)	156
O1W—H1W···O3vii	0.84	2.12	2.947 (2)	172

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2⋯O1i	0.86	2.01	2.859 (2)	171
O1W—H2W⋯O1ii	0.83	2.31	3.088 (2)	156
O1W—H1W⋯O3iii	0.84	2.12	2.947 (2)	172

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