The structure of the title compound, [Ca(C4H3N2O2)2(H2O)]n, is composed of molecular ribbons in which the CaII ions are bridged by two symmetry-independent imidazole-4-carboxylate ligands. Each CaII 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 CaII 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.
Supporting information
CCDC reference: 280864
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (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
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']
top
Crystal data top
[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) Å3 | Rectangular plates, colourless |
Z = 4 | 0.40 × 0.29 × 0.10 mm |
Data collection top
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 top
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)] = 0.037 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.124 | All H-atom parameters refined |
S = 1.06 | w = 1/[σ2(Fo2) + (0.0857P)2 + 0.4634P] where P = (Fo2 + 2Fc2)/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 top
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 (Å2) top | 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 (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
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) top
Ca1—O11i | 2.3836 (13) | N13—C14 | 1.381 (2) |
Ca1—O31 | 2.4120 (15) | C16—C14 | 1.479 (2) |
Ca1—O12ii | 2.4522 (14) | O31—H31 | 0.85 (4) |
Ca1—O22iii | 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—Ca1iii | 3.6906 (10) | N11—H11 | 0.86 (3) |
Ca1—Ca1i | 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—Ca1i | 2.3836 (13) | C12—H12 | 0.96 (3) |
O12—C16 | 1.2583 (19) | N21—C22 | 1.338 (3) |
O12—Ca1iv | 2.4522 (14) | N21—C25 | 1.358 (3) |
O22—C26 | 1.264 (2) | N21—H21 | 0.88 (4) |
O22—Ca1iii | 2.4646 (14) | C25—H25 | 0.88 (3) |
O21—C26 | 1.254 (2) | C22—H22 | 0.92 (3) |
N13—C12 | 1.311 (2) | | |
| | | |
O11i—Ca1—O31 | 94.42 (5) | O12ii—Ca1—H31 | 114.2 (8) |
O11i—Ca1—O12ii | 143.84 (4) | O22iii—Ca1—H31 | 79.3 (7) |
O31—Ca1—O12ii | 96.82 (5) | N13—Ca1—H31 | 88.7 (7) |
O11i—Ca1—O22iii | 73.75 (4) | O11—Ca1—H31 | 58.1 (8) |
O31—Ca1—O22iii | 76.69 (5) | O21—Ca1—H31 | 131.4 (8) |
O12ii—Ca1—O22iii | 75.62 (5) | O22—Ca1—H31 | 157.7 (7) |
O11i—Ca1—N13 | 137.92 (5) | C26—Ca1—H31 | 150.9 (8) |
O31—Ca1—N13 | 81.37 (5) | Ca1iii—Ca1—H31 | 120.6 (7) |
O12ii—Ca1—N13 | 77.89 (5) | Ca1i—Ca1—H31 | 62.7 (8) |
O22iii—Ca1—N13 | 143.02 (5) | C16—O11—Ca1i | 133.29 (10) |
O11i—Ca1—O11 | 72.90 (5) | C16—O11—Ca1 | 118.67 (10) |
O31—Ca1—O11 | 69.75 (5) | Ca1i—O11—Ca1 | 107.10 (5) |
O12ii—Ca1—O11 | 143.07 (4) | C16—O12—Ca1iv | 133.57 (10) |
O22iii—Ca1—O11 | 129.84 (5) | C26—O22—Ca1iii | 147.76 (11) |
N13—Ca1—O11 | 66.35 (5) | C26—O22—Ca1 | 92.84 (10) |
O11i—Ca1—O21 | 75.02 (5) | Ca1iii—O22—Ca1 | 95.28 (4) |
O31—Ca1—O21 | 145.17 (5) | C26—O21—Ca1 | 93.20 (10) |
O12ii—Ca1—O21 | 111.36 (5) | C12—N13—C14 | 105.36 (14) |
O22iii—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) |
O11i—Ca1—O22 | 82.30 (5) | O11—C16—C14 | 116.32 (13) |
O31—Ca1—O22 | 161.28 (5) | O12—C16—C14 | 118.02 (14) |
O12ii—Ca1—O22 | 76.16 (4) | Ca1—O31—H31 | 103 (2) |
O22iii—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) |
O11i—Ca1—C26 | 76.32 (4) | N23—C24—C26 | 122.31 (16) |
O31—Ca1—C26 | 168.33 (5) | O21—C26—O22 | 122.10 (15) |
O12ii—Ca1—C26 | 94.84 (5) | O21—C26—C24 | 118.59 (15) |
O22iii—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) |
O11i—Ca1—Ca1iii | 73.81 (3) | C12—N11—H11 | 123 (2) |
O31—Ca1—Ca1iii | 119.70 (4) | C15—N11—H11 | 128 (2) |
O12ii—Ca1—Ca1iii | 70.75 (3) | C15—C14—N13 | 109.49 (14) |
O22iii—Ca1—Ca1iii | 43.04 (3) | C15—C14—C16 | 129.32 (15) |
N13—Ca1—Ca1iii | 143.61 (4) | N13—C14—C16 | 120.90 (14) |
O11—Ca1—Ca1iii | 146.03 (3) | N11—C15—C14 | 105.96 (15) |
O21—Ca1—Ca1iii | 89.65 (3) | N11—C15—H15 | 120.8 (17) |
O22—Ca1—Ca1iii | 41.68 (3) | C14—C15—H15 | 133.1 (17) |
C26—Ca1—Ca1iii | 65.00 (3) | C22—N23—C24 | 105.55 (18) |
O11i—Ca1—Ca1i | 37.56 (3) | N13—C12—N11 | 111.47 (16) |
O31—Ca1—Ca1i | 79.98 (4) | N13—C12—H12 | 125.0 (15) |
O12ii—Ca1—Ca1i | 176.77 (3) | N11—C12—H12 | 123.5 (15) |
O22iii—Ca1—Ca1i | 103.84 (4) | C22—N21—C25 | 107.37 (17) |
N13—Ca1—Ca1i | 101.15 (4) | C22—N21—H21 | 124 (2) |
O11—Ca1—Ca1i | 35.34 (3) | C25—N21—H21 | 128 (2) |
O21—Ca1—Ca1i | 71.52 (3) | N21—C25—C24 | 106.05 (18) |
O22—Ca1—Ca1i | 107.00 (3) | N21—C25—H25 | 120 (2) |
C26—Ca1—Ca1i | 88.36 (3) | C24—C25—H25 | 133 (2) |
Ca1iii—Ca1—Ca1i | 111.11 (2) | N23—C22—N21 | 111.7 (2) |
O11i—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) top
D—H···A | D—H | H···A | D···A | D—H···A |
N21—H21···O12v | 0.88 (4) | 1.95 (4) | 2.825 (2) | 175 (3) |
O31—H31···O21i | 0.85 (4) | 2.01 (4) | 2.844 (2) | 168 (3) |
N11—H11···O22vi | 0.86 (3) | 2.29 (3) | 2.995 (2) | 140 (3) |
O31—H32···N23iii | 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. |