catena-Poly[[aqua­calcium(II)]bis­(μ-1H-imidazole-4-carboxyl­ato)-κ⁴N,O:O,O′;κ³O,O′:O′]

The structure of the title compound, [Ca(C₄H₃N₂O₂)₂(H₂O)]_n, is composed of mol­ecular ribbons in which the Ca^II ions are bridged by two symmetry-independent imidazole-4-carboxyl­ate ligands. Each Ca^II ion is coordinated by the N,O-bonding group of one ligand, two carboxyl­ate O atoms of the other ligand, an O atom of the coordinated water mol­ecule and three bridging carboxyl­ate O atoms donated by both ligands. The coordination polyhedron of the Ca^II ion (coordination number 8) is a bicapped penta­gonal bipyramid with a strongly deformed equatorial plane. The ribbons are held together by a network of hydrogen bonds.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.002 Å
• R factor = 0.036
• wR factor = 0.124
• Data-to-parameter ratio = 16.1

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given .......          ?
PLAT164_ALERT_4_C Nr. of Refined C-H H-Atoms in Heavy-At Struct...          4
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       2.95 Ratio
PLAT764_ALERT_4_C Overcomplete CIF Bond List Detected (Rep/Expd) .       1.25 Ratio

Alert level G
PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature        293 K
PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature .        293 K

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   4 ALERT level C = Check and explain
   2 ALERT level G = General alerts; check

   2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   1 ALERT type 2 Indicator that the structure model may be wrong or deficient
   0 ALERT type 3 Indicator that the structure quality may be low
   3 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

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Computing details

Data collection: DATAPROC (Kuma, 2001); cell refinement: DATAPROC; data reduction: DATAPROC; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997).

catena-Poly[aquacalcium(II)]bis(µ-imidazole-4-carboxylato)- κ⁴N,O:O,O';κ³O,O':O']

Crystal data

[Ca(C4H3N2O2)2(H2O)]	F(000) = 576
Mr = 280.26	Dx = 1.729 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 6.2930 (13) Å	Cell parameters from 25 reflections
b = 19.784 (4) Å	θ = 6–15°
c = 8.7620 (18) Å	µ = 0.61 mm^−1
β = 99.24 (3)°	T = 293 K
V = 1076.7 (4) Å^3	Rectangular plates, colourless
Z = 4	0.40 × 0.29 × 0.10 mm

Data collection

Kuma KM-4 4-circle diffractometer	2592 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.019
Graphite monochromator	θmax = 30.1°, θmin = 2.1°
ω/2θ scan	h = 0→8
Absorption correction: analytical (CrysAlis RED; Oxford Diffraction, 2000)	k = 0→27
Tmin = 0.692, Tmax = 0.871	l = −12→12
3406 measured reflections	3 standard reflections every 200 reflections
3147 independent reflections	intensity decay: 2.3%

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.037	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.124	All H-atom parameters refined
S = 1.06	w = 1/[σ^2(Fo^2) + (0.0857P)^2 + 0.4634P] where P = (Fo^2 + 2Fc^2)/3
3147 reflections	(Δ/σ)max = 0.002
195 parameters	Δρmax = 0.60 e Å^−3
0 restraints	Δρmin = −0.97 e Å^−3

Special details

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.

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

	x	y	z	Uiso*/Ueq
Ca1	0.21422 (5)	0.528141 (15)	0.39335 (3)	0.01386 (11)
O11	0.60779 (19)	0.52260 (6)	0.37409 (13)	0.0169 (2)
O12	0.86580 (18)	0.56976 (6)	0.26103 (15)	0.0200 (3)
O22	−0.0346 (2)	0.42793 (6)	0.39700 (15)	0.0203 (2)
O21	0.2765 (2)	0.40681 (7)	0.32185 (16)	0.0253 (3)
N13	0.2950 (2)	0.55511 (8)	0.12888 (17)	0.0193 (3)
C16	0.6737 (2)	0.55318 (7)	0.26503 (17)	0.0137 (3)
O31	0.3797 (2)	0.63727 (7)	0.44858 (18)	0.0287 (3)
C24	0.0479 (3)	0.31452 (9)	0.3433 (2)	0.0221 (3)
C26	0.1005 (3)	0.38724 (8)	0.35611 (18)	0.0174 (3)
N11	0.3388 (3)	0.59186 (9)	−0.10047 (18)	0.0268 (3)
C14	0.5099 (2)	0.56939 (8)	0.12927 (18)	0.0162 (3)
C15	0.5372 (3)	0.59250 (10)	−0.0127 (2)	0.0229 (3)
N23	−0.1456 (3)	0.28937 (9)	0.3709 (2)	0.0333 (4)
C12	0.1984 (3)	0.56929 (10)	−0.0114 (2)	0.0243 (4)
N21	0.0497 (3)	0.20610 (9)	0.3041 (3)	0.0385 (5)
C25	0.1696 (4)	0.26300 (10)	0.3011 (3)	0.0347 (5)
C22	−0.1380 (4)	0.22438 (10)	0.3452 (3)	0.0404 (5)
H21	0.082 (5)	0.1647 (18)	0.281 (4)	0.054 (9)*
H25	0.296 (6)	0.2612 (18)	0.271 (4)	0.052 (9)*
H15	0.662 (5)	0.6057 (15)	−0.056 (3)	0.039 (7)*
H22	−0.251 (5)	0.1954 (16)	0.352 (3)	0.039 (7)*
H12	0.047 (4)	0.5652 (13)	−0.047 (3)	0.030 (6)*
H31	0.494 (6)	0.6276 (17)	0.510 (4)	0.053 (9)*
H11	0.305 (5)	0.5981 (16)	−0.199 (4)	0.045 (8)*
H32	0.314 (6)	0.6590 (18)	0.501 (4)	0.053 (9)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Ca1	0.01120 (16)	0.01355 (17)	0.01725 (17)	0.00022 (9)	0.00356 (11)	0.00241 (10)
O11	0.0144 (5)	0.0202 (5)	0.0167 (5)	0.0015 (4)	0.0041 (4)	0.0051 (4)
O12	0.0114 (5)	0.0217 (6)	0.0272 (6)	−0.0011 (4)	0.0035 (4)	0.0071 (5)
O22	0.0201 (6)	0.0141 (5)	0.0272 (6)	0.0012 (4)	0.0052 (4)	−0.0012 (4)
O21	0.0234 (6)	0.0219 (6)	0.0332 (7)	−0.0029 (5)	0.0128 (5)	−0.0028 (5)
N13	0.0130 (6)	0.0236 (7)	0.0212 (6)	0.0009 (5)	0.0026 (5)	0.0028 (5)
C16	0.0116 (6)	0.0122 (6)	0.0177 (6)	0.0012 (5)	0.0032 (5)	0.0004 (5)
O31	0.0233 (6)	0.0235 (7)	0.0402 (8)	0.0002 (5)	0.0079 (6)	−0.0061 (6)
C24	0.0210 (8)	0.0152 (7)	0.0303 (8)	0.0016 (6)	0.0045 (6)	−0.0034 (6)
C26	0.0191 (7)	0.0145 (7)	0.0179 (7)	0.0016 (5)	0.0009 (5)	−0.0005 (5)
N11	0.0253 (7)	0.0388 (9)	0.0160 (7)	0.0064 (7)	0.0023 (5)	0.0067 (6)
C14	0.0128 (6)	0.0185 (7)	0.0174 (7)	0.0017 (5)	0.0029 (5)	0.0023 (5)
C15	0.0193 (7)	0.0301 (9)	0.0202 (7)	0.0033 (6)	0.0056 (6)	0.0060 (6)
N23	0.0280 (8)	0.0161 (7)	0.0588 (12)	−0.0033 (6)	0.0156 (8)	−0.0072 (7)
C12	0.0168 (7)	0.0313 (9)	0.0237 (8)	0.0030 (6)	−0.0003 (6)	0.0024 (7)
N21	0.0386 (10)	0.0161 (8)	0.0612 (13)	0.0037 (7)	0.0093 (9)	−0.0109 (7)
C25	0.0288 (10)	0.0215 (9)	0.0557 (13)	0.0043 (7)	0.0127 (9)	−0.0097 (9)
C22	0.0375 (11)	0.0163 (9)	0.0696 (16)	−0.0059 (8)	0.0153 (11)	−0.0097 (9)

Geometric parameters (Å, º)

Ca1—O11^i	2.3836 (13)	N13—C14	1.381 (2)
Ca1—O31	2.4120 (15)	C16—C14	1.479 (2)
Ca1—O12^ii	2.4522 (14)	O31—H31	0.85 (4)
Ca1—O22^iii	2.4646 (14)	O31—H32	0.79 (4)
Ca1—N13	2.5082 (16)	C24—C25	1.361 (2)
Ca1—O11	2.5117 (13)	C24—N23	1.372 (2)
Ca1—O21	2.5273 (15)	C24—C26	1.477 (2)
Ca1—O22	2.5297 (13)	N11—C12	1.346 (3)
Ca1—C26	2.8833 (17)	N11—C15	1.357 (2)
Ca1—Ca1^iii	3.6906 (10)	N11—H11	0.86 (3)
Ca1—Ca1^i	3.9384 (12)	C14—C15	1.362 (2)
Ca1—H31	2.73 (3)	C15—H15	0.96 (3)
O11—C16	1.2564 (19)	N23—C22	1.308 (3)
O11—Ca1^i	2.3836 (13)	C12—H12	0.96 (3)
O12—C16	1.2583 (19)	N21—C22	1.338 (3)
O12—Ca1^iv	2.4522 (14)	N21—C25	1.358 (3)
O22—C26	1.264 (2)	N21—H21	0.88 (4)
O22—Ca1^iii	2.4646 (14)	C25—H25	0.88 (3)
O21—C26	1.254 (2)	C22—H22	0.92 (3)
N13—C12	1.311 (2)
O11^i—Ca1—O31	94.42 (5)	O12^ii—Ca1—H31	114.2 (8)
O11^i—Ca1—O12^ii	143.84 (4)	O22^iii—Ca1—H31	79.3 (7)
O31—Ca1—O12^ii	96.82 (5)	N13—Ca1—H31	88.7 (7)
O11^i—Ca1—O22^iii	73.75 (4)	O11—Ca1—H31	58.1 (8)
O31—Ca1—O22^iii	76.69 (5)	O21—Ca1—H31	131.4 (8)
O12^ii—Ca1—O22^iii	75.62 (5)	O22—Ca1—H31	157.7 (7)
O11^i—Ca1—N13	137.92 (5)	C26—Ca1—H31	150.9 (8)
O31—Ca1—N13	81.37 (5)	Ca1^iii—Ca1—H31	120.6 (7)
O12^ii—Ca1—N13	77.89 (5)	Ca1^i—Ca1—H31	62.7 (8)
O22^iii—Ca1—N13	143.02 (5)	C16—O11—Ca1^i	133.29 (10)
O11^i—Ca1—O11	72.90 (5)	C16—O11—Ca1	118.67 (10)
O31—Ca1—O11	69.75 (5)	Ca1^i—O11—Ca1	107.10 (5)
O12^ii—Ca1—O11	143.07 (4)	C16—O12—Ca1^iv	133.57 (10)
O22^iii—Ca1—O11	129.84 (5)	C26—O22—Ca1^iii	147.76 (11)
N13—Ca1—O11	66.35 (5)	C26—O22—Ca1	92.84 (10)
O11^i—Ca1—O21	75.02 (5)	Ca1^iii—O22—Ca1	95.28 (4)
O31—Ca1—O21	145.17 (5)	C26—O21—Ca1	93.20 (10)
O12^ii—Ca1—O21	111.36 (5)	C12—N13—C14	105.36 (14)
O22^iii—Ca1—O21	128.87 (4)	C12—N13—Ca1	141.20 (12)
N13—Ca1—O21	84.87 (5)	C14—N13—Ca1	112.64 (11)
O11—Ca1—O21	75.41 (4)	O11—C16—O12	125.64 (14)
O11^i—Ca1—O22	82.30 (5)	O11—C16—C14	116.32 (13)
O31—Ca1—O22	161.28 (5)	O12—C16—C14	118.02 (14)
O12^ii—Ca1—O22	76.16 (4)	Ca1—O31—H31	103 (2)
O22^iii—Ca1—O22	84.72 (4)	Ca1—O31—H32	111 (3)
N13—Ca1—O22	113.33 (5)	H31—O31—H32	103 (3)
O11—Ca1—O22	125.85 (4)	C25—C24—N23	109.29 (17)
O21—Ca1—O22	51.66 (4)	C25—C24—C26	128.38 (18)
O11^i—Ca1—C26	76.32 (4)	N23—C24—C26	122.31 (16)
O31—Ca1—C26	168.33 (5)	O21—C26—O22	122.10 (15)
O12^ii—Ca1—C26	94.84 (5)	O21—C26—C24	118.59 (15)
O22^iii—Ca1—C26	106.86 (5)	O22—C26—C24	119.28 (15)
N13—Ca1—C26	100.63 (5)	O21—C26—Ca1	61.06 (9)
O11—Ca1—C26	100.35 (4)	O22—C26—Ca1	61.20 (9)
O21—Ca1—C26	25.74 (4)	C24—C26—Ca1	177.63 (12)
O22—Ca1—C26	25.96 (4)	C12—N11—C15	107.72 (15)
O11^i—Ca1—Ca1^iii	73.81 (3)	C12—N11—H11	123 (2)
O31—Ca1—Ca1^iii	119.70 (4)	C15—N11—H11	128 (2)
O12^ii—Ca1—Ca1^iii	70.75 (3)	C15—C14—N13	109.49 (14)
O22^iii—Ca1—Ca1^iii	43.04 (3)	C15—C14—C16	129.32 (15)
N13—Ca1—Ca1^iii	143.61 (4)	N13—C14—C16	120.90 (14)
O11—Ca1—Ca1^iii	146.03 (3)	N11—C15—C14	105.96 (15)
O21—Ca1—Ca1^iii	89.65 (3)	N11—C15—H15	120.8 (17)
O22—Ca1—Ca1^iii	41.68 (3)	C14—C15—H15	133.1 (17)
C26—Ca1—Ca1^iii	65.00 (3)	C22—N23—C24	105.55 (18)
O11^i—Ca1—Ca1^i	37.56 (3)	N13—C12—N11	111.47 (16)
O31—Ca1—Ca1^i	79.98 (4)	N13—C12—H12	125.0 (15)
O12^ii—Ca1—Ca1^i	176.77 (3)	N11—C12—H12	123.5 (15)
O22^iii—Ca1—Ca1^i	103.84 (4)	C22—N21—C25	107.37 (17)
N13—Ca1—Ca1^i	101.15 (4)	C22—N21—H21	124 (2)
O11—Ca1—Ca1^i	35.34 (3)	C25—N21—H21	128 (2)
O21—Ca1—Ca1^i	71.52 (3)	N21—C25—C24	106.05 (18)
O22—Ca1—Ca1^i	107.00 (3)	N21—C25—H25	120 (2)
C26—Ca1—Ca1^i	88.36 (3)	C24—C25—H25	133 (2)
Ca1^iii—Ca1—Ca1^i	111.11 (2)	N23—C22—N21	111.7 (2)
O11^i—Ca1—H31	78.4 (8)	N23—C22—H22	123.3 (19)
O31—Ca1—H31	17.6 (7)	N21—C22—H22	125.0 (19)

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

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N21—H21···O12^v	0.88 (4)	1.95 (4)	2.825 (2)	175 (3)
O31—H31···O21^i	0.85 (4)	2.01 (4)	2.844 (2)	168 (3)
N11—H11···O22^vi	0.86 (3)	2.29 (3)	2.995 (2)	140 (3)
O31—H32···N23^iii	0.79 (4)	1.95 (4)	2.743 (2)	178 (4)

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