Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807037312/bt2460sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807037312/bt2460Isup2.hkl |
CCDC reference: 660051
Key indicators
- Single-crystal X-ray study
- T = 295 K
- Mean (C-C) = 0.002 Å
- R factor = 0.030
- wR factor = 0.086
- Data-to-parameter ratio = 11.9
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT152_ALERT_1_C Supplied and Calc Volume s.u. Inconsistent ..... ? PLAT164_ALERT_4_C Nr. of Refined C-H H-Atoms in Heavy-At Struct... 1
Alert level G PLAT794_ALERT_5_G Check Predicted Bond Valency for Co1 (2) 2.14 PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints ....... 5
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 2 ALERT level C = Check and explain 2 ALERT level G = General alerts; check 1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 0 ALERT type 2 Indicator that the structure model may be wrong or deficient 1 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion 1 ALERT type 5 Informative message, check
For the crystal structure of 2,4-dihydroxypyridimine-5-carboxylic acid, see Law et al. (2004). For the crystal structures of other water-coordinated metal derivatives, see Maistralis et al. (1991) (Mn), Baran et al. (1996) (Fe), Sun & Jin (2004) (Fe and Co) and Luo et al. (2002) (Cu).
Cobalt(II) acetate hexahydrate (0.062 g, 0.25 mmol) and 2,4-dihydroxypyrimidine-5-carboxylic acid (0.087 g, 0.5 mmol) were placed in a 23-ml, Telefon-lined, stainless-steel Parr bomb together with water (6 ml) and THF (4 ml). The bomb was heated to 383 K for 144 h; it was then cooled over 48 h. Pink crystals were isolated in 70% yield.
All hydrogen atoms were located in a difference Fourier map, and were refined with distance restraints of C—H 0.95 (1) Å, N—H = O—H = 0.85 (1) Å. Their temperature factors were freely refined.
2,4-Dihydroxypyridimine-5-carboxylic acid crystallizes as a monohydrate; the 2,4-dihydroxypyrimidinyl portion of the molecule exists a 2,4-dioxo-1,2,3,4-tetrahydropyrimidinyl entity having secondary nitrogen atoms and exocyclic carbon–oxygen double bonds (Law et al., 2004). The features are retained in the diaquamanganese(II) (Maistralis et al., 1991), dihydrated diaquairon(II) (Baran et al., 1996), triaquacobalt(II), triaquanickel(II) (Sun & Jin, 2004) and diaquacopper(II) (Luo et al., 2002) derivatives; the anion chelates to the metal atoms through the 5-carboxylato and 4-oxo oxygen atoms. The diaquamanganese (Maistralis et al., 1991), diaquacopper (Luo et al., 2002) and the present diaquacobalt(II) compounds are isostructural; two carboxylate monoanions chelate in this manner across a center of inversion. Hydrogen bonds link adjacent octahedral molecules into a three-dimensional network.
For the crystal structure of 2,4-dihydroxypyridimine-5-carboxylic acid, see Law et al. (2004). For the crystal structures of other water-coordinated metal derivatives, see Maistralis et al. (1991) (Mn), Baran et al. (1996) (Fe), Sun & Jin (2004) (Fe and Co) and Luo et al. (2002) (Cu).
Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: X-SEED (Barbour, 2001); software used to prepare material for publication: publCIF (Westrip, 2007).
Fig. 1. Thermal ellipsoid plot of Co(C5H3N2O4)2(H2O)2. The molecule lies about a center-of-inversion, and the unlabeled atoms are related to the labeled ones by 1 - x, 1 - y, 1 - z. |
[Co(C5H3N2O4)2(H2O)2] | F(000) = 410 |
Mr = 405.15 | Dx = 1.923 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2yn | Cell parameters from 1901 reflections |
a = 5.0608 (6) Å | θ = 2.6–27.5° |
b = 15.087 (2) Å | µ = 1.30 mm−1 |
c = 9.290 (1) Å | T = 295 K |
β = 99.389 (1)° | Block, pink |
V = 699.8 (2) Å3 | 0.20 × 0.20 × 0.10 mm |
Z = 2 |
Bruker APEXII area-detector diffractometer | 1605 independent reflections |
Radiation source: fine-focus sealed tube | 1308 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.020 |
φ and ω scans | θmax = 27.5°, θmin = 2.6° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −6→6 |
Tmin = 0.743, Tmax = 0.881 | k = −19→17 |
4291 measured reflections | l = −9→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)] = 0.030 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.086 | All H-atom parameters refined |
S = 1.05 | w = 1/[σ2(Fo2) + (0.0481P)2 + 0.1507P] where P = (Fo2 + 2Fc2)/3 |
1605 reflections | (Δ/σ)max = 0.001 |
135 parameters | Δρmax = 0.31 e Å−3 |
5 restraints | Δρmin = −0.29 e Å−3 |
[Co(C5H3N2O4)2(H2O)2] | V = 699.8 (2) Å3 |
Mr = 405.15 | Z = 2 |
Monoclinic, P21/n | Mo Kα radiation |
a = 5.0608 (6) Å | µ = 1.30 mm−1 |
b = 15.087 (2) Å | T = 295 K |
c = 9.290 (1) Å | 0.20 × 0.20 × 0.10 mm |
β = 99.389 (1)° |
Bruker APEXII area-detector diffractometer | 1605 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | 1308 reflections with I > 2σ(I) |
Tmin = 0.743, Tmax = 0.881 | Rint = 0.020 |
4291 measured reflections |
R[F2 > 2σ(F2)] = 0.030 | 5 restraints |
wR(F2) = 0.086 | All H-atom parameters refined |
S = 1.05 | Δρmax = 0.31 e Å−3 |
1605 reflections | Δρmin = −0.29 e Å−3 |
135 parameters |
x | y | z | Uiso*/Ueq | ||
Co1 | 0.5000 | 0.5000 | 0.5000 | 0.02430 (14) | |
O1 | 0.2334 (3) | 0.4047 (1) | 0.4163 (2) | 0.0289 (3) | |
O2 | 0.0616 (3) | 0.2948 (1) | 0.2730 (2) | 0.0292 (3) | |
O3 | 0.6389 (3) | 0.5050 (1) | 0.3040 (2) | 0.0267 (3) | |
O4 | 0.8892 (3) | 0.4044 (1) | −0.1094 (2) | 0.0314 (4) | |
O1W | 0.7933 (3) | 0.4003 (1) | 0.5678 (2) | 0.0322 (4) | |
N1 | 0.5619 (4) | 0.3281 (1) | −0.0207 (2) | 0.0264 (4) | |
N2 | 0.7483 (3) | 0.4527 (1) | 0.0975 (2) | 0.0223 (4) | |
C1 | 0.2244 (4) | 0.3567 (1) | 0.3041 (2) | 0.0218 (4) | |
C2 | 0.4114 (4) | 0.3746 (1) | 0.1976 (2) | 0.0219 (4) | |
C3 | 0.4047 (4) | 0.3190 (1) | 0.0823 (2) | 0.0257 (4) | |
C4 | 0.7430 (4) | 0.3953 (1) | −0.0169 (2) | 0.0240 (4) | |
C5 | 0.5999 (4) | 0.4468 (1) | 0.2087 (2) | 0.0215 (4) | |
H11 | 0.930 (4) | 0.403 (2) | 0.527 (3) | 0.07 (1)* | |
H12 | 0.842 (5) | 0.394 (2) | 0.659 (1) | 0.05 (1)* | |
H1 | 0.557 (5) | 0.288 (1) | −0.085 (2) | 0.04 (1)* | |
H2 | 0.848 (5) | 0.498 (1) | 0.107 (3) | 0.04 (1)* | |
H3 | 0.289 (4) | 0.270 (1) | 0.064 (2) | 0.03 (1)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Co1 | 0.0236 (2) | 0.0294 (2) | 0.0220 (2) | −0.0043 (2) | 0.0099 (2) | −0.0052 (2) |
O1 | 0.0257 (7) | 0.0373 (8) | 0.0264 (8) | −0.0079 (6) | 0.0118 (6) | −0.0074 (6) |
O2 | 0.0324 (8) | 0.0296 (8) | 0.0266 (8) | −0.0086 (6) | 0.0071 (6) | 0.0023 (6) |
O3 | 0.0303 (8) | 0.0298 (8) | 0.0223 (8) | −0.0066 (6) | 0.0114 (6) | −0.0064 (6) |
O4 | 0.0318 (8) | 0.0403 (9) | 0.0249 (8) | −0.0068 (6) | 0.0130 (6) | −0.0051 (6) |
O1W | 0.0298 (9) | 0.0377 (9) | 0.0309 (9) | 0.0008 (7) | 0.0104 (7) | 0.0001 (7) |
N1 | 0.0294 (9) | 0.0270 (9) | 0.0245 (9) | −0.0028 (7) | 0.0091 (7) | −0.0066 (7) |
N2 | 0.0230 (9) | 0.0247 (9) | 0.0204 (8) | −0.0033 (7) | 0.0075 (7) | −0.0015 (7) |
C1 | 0.021 (1) | 0.024 (1) | 0.021 (1) | 0.002 (1) | 0.005 (1) | 0.003 (1) |
C2 | 0.022 (1) | 0.023 (1) | 0.022 (1) | 0.000 (1) | 0.006 (1) | 0.000 (1) |
C3 | 0.025 (1) | 0.024 (1) | 0.029 (1) | −0.002 (1) | 0.008 (1) | −0.001 (1) |
C4 | 0.022 (1) | 0.028 (1) | 0.022 (1) | 0.001 (1) | 0.006 (1) | 0.000 (1) |
C5 | 0.021 (1) | 0.024 (1) | 0.020 (1) | 0.002 (1) | 0.006 (1) | 0.003 (1) |
Co1—O1 | 2.037 (1) | N1—C4 | 1.364 (3) |
Co1—O1i | 2.037 (1) | N2—C4 | 1.367 (2) |
Co1—O3 | 2.058 (1) | N2—C5 | 1.376 (2) |
Co1—O3i | 2.058 (1) | C1—C2 | 1.501 (3) |
Co1—O1W | 2.135 (2) | C2—C3 | 1.357 (3) |
Co1—O1Wi | 2.135 (2) | C2—C5 | 1.440 (3) |
O1—C1 | 1.265 (2) | O1W—H11 | 0.85 (1) |
O2—C1 | 1.247 (2) | O1W—H12 | 0.85 (1) |
O3—C5 | 1.239 (2) | N1—H1 | 0.85 (1) |
O4—C4 | 1.230 (2) | N2—H2 | 0.85 (1) |
N1—C3 | 1.347 (3) | C3—H3 | 0.94 (1) |
O1i—Co1—O1 | 180.0 | O1—C1—C2 | 119.9 (2) |
O1i—Co1—O3i | 89.33 (5) | C3—C2—C5 | 117.1 (2) |
O1—Co1—O3i | 90.67 (5) | C3—C2—C1 | 118.1 (2) |
O1i—Co1—O3 | 90.67 (5) | C5—C2—C1 | 124.8 (2) |
O1—Co1—O3 | 89.33 (5) | N1—C3—C2 | 123.8 (2) |
O3i—Co1—O3 | 180.0 | O4—C4—N1 | 122.9 (2) |
O1i—Co1—O1W | 89.97 (7) | O4—C4—N2 | 122.3 (2) |
O1—Co1—O1W | 90.03 (7) | N1—C4—N2 | 114.8 (2) |
O3i—Co1—O1W | 92.00 (6) | O3—C5—N2 | 116.6 (2) |
O3—Co1—O1W | 88.00 (6) | O3—C5—C2 | 127.8 (2) |
O1i—Co1—O1Wi | 90.03 (7) | N2—C5—C2 | 115.5 (2) |
O1—Co1—O1Wi | 89.97 (7) | Co1—O1W—H11 | 114 (2) |
O3i—Co1—O1Wi | 88.00 (6) | Co1—O1W—H12 | 117 (2) |
O3—Co1—O1Wi | 92.00 (6) | H11—O1W—H12 | 109 (3) |
O1W—Co1—O1Wi | 180.0 | C3—N1—H1 | 118 (2) |
C1—O1—Co1 | 130.7 (1) | C4—N1—H1 | 120 (2) |
C5—O3—Co1 | 124.7 (1) | C4—N2—H2 | 122 (2) |
C3—N1—C4 | 122.0 (2) | C5—N2—H2 | 111 (2) |
C4—N2—C5 | 126.8 (2) | N1—C3—H3 | 112.0 (13) |
O2—C1—O1 | 123.6 (2) | C2—C3—H3 | 124.2 (13) |
O2—C1—C2 | 116.5 (2) | ||
O3i—Co1—O1—C1 | −164.2 (2) | C5—C2—C3—N1 | −0.4 (3) |
O3—Co1—O1—C1 | 15.8 (2) | C1—C2—C3—N1 | 179.9 (2) |
O1W—Co1—O1—C1 | −72.2 (2) | C3—N1—C4—O4 | 179.6 (2) |
O1Wi—Co1—O1—C1 | 107.8 (2) | C3—N1—C4—N2 | −1.0 (3) |
O1i—Co1—O3—C5 | 162.5 (2) | C5—N2—C4—O4 | −177.8 (2) |
O1—Co1—O3—C5 | −17.5 (2) | C5—N2—C4—N1 | 2.8 (3) |
O1W—Co1—O3—C5 | 72.5 (2) | Co1—O3—C5—N2 | −168.1 (1) |
O1Wi—Co1—O3—C5 | −107.5 (2) | Co1—O3—C5—C2 | 13.9 (3) |
Co1—O1—C1—O2 | 173.1 (1) | C4—N2—C5—O3 | 178.5 (2) |
Co1—O1—C1—C2 | −8.7 (3) | C4—N2—C5—C2 | −3.2 (3) |
O2—C1—C2—C3 | −4.9 (3) | C3—C2—C5—O3 | 179.9 (2) |
O1—C1—C2—C3 | 176.8 (2) | C1—C2—C5—O3 | −0.4 (3) |
O2—C1—C2—C5 | 175.4 (2) | C3—C2—C5—N2 | 1.8 (3) |
O1—C1—C2—C5 | −2.9 (3) | C1—C2—C5—N2 | −178.5 (2) |
C4—N1—C3—C2 | −0.1 (3) |
Symmetry code: (i) −x+1, −y+1, −z+1. |
D—H···A | D—H | H···A | D···A | D—H···A |
O1W—H11···O1ii | 0.85 (1) | 1.98 (1) | 2.823 (2) | 175 (3) |
O1W—H12···O4iii | 0.85 (1) | 2.14 (1) | 2.959 (2) | 165 (3) |
N1—H1···O2iv | 0.85 (1) | 1.81 (1) | 2.667 (2) | 177 (3) |
N2—H2···O4v | 0.85 (1) | 1.98 (1) | 2.822 (2) | 171 (3) |
Symmetry codes: (ii) x+1, y, z; (iii) x, y, z+1; (iv) x+1/2, −y+1/2, z−1/2; (v) −x+2, −y+1, −z. |
Experimental details
Crystal data | |
Chemical formula | [Co(C5H3N2O4)2(H2O)2] |
Mr | 405.15 |
Crystal system, space group | Monoclinic, P21/n |
Temperature (K) | 295 |
a, b, c (Å) | 5.0608 (6), 15.087 (2), 9.290 (1) |
β (°) | 99.389 (1) |
V (Å3) | 699.8 (2) |
Z | 2 |
Radiation type | Mo Kα |
µ (mm−1) | 1.30 |
Crystal size (mm) | 0.20 × 0.20 × 0.10 |
Data collection | |
Diffractometer | Bruker APEXII area-detector |
Absorption correction | Multi-scan (SADABS; Sheldrick, 1996) |
Tmin, Tmax | 0.743, 0.881 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 4291, 1605, 1308 |
Rint | 0.020 |
(sin θ/λ)max (Å−1) | 0.650 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.030, 0.086, 1.05 |
No. of reflections | 1605 |
No. of parameters | 135 |
No. of restraints | 5 |
H-atom treatment | All H-atom parameters refined |
Δρmax, Δρmin (e Å−3) | 0.31, −0.29 |
Computer programs: APEX2 (Bruker, 2004), SAINT (Bruker, 2004), SAINT, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), X-SEED (Barbour, 2001), publCIF (Westrip, 2007).
D—H···A | D—H | H···A | D···A | D—H···A |
O1W—H11···O1i | 0.85 (1) | 1.98 (1) | 2.823 (2) | 175 (3) |
O1W—H12···O4ii | 0.85 (1) | 2.14 (1) | 2.959 (2) | 165 (3) |
N1—H1···O2iii | 0.85 (1) | 1.81 (1) | 2.667 (2) | 177 (3) |
N2—H2···O4iv | 0.85 (1) | 1.98 (1) | 2.822 (2) | 171 (3) |
Symmetry codes: (i) x+1, y, z; (ii) x, y, z+1; (iii) x+1/2, −y+1/2, z−1/2; (iv) −x+2, −y+1, −z. |
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2,4-Dihydroxypyridimine-5-carboxylic acid crystallizes as a monohydrate; the 2,4-dihydroxypyrimidinyl portion of the molecule exists a 2,4-dioxo-1,2,3,4-tetrahydropyrimidinyl entity having secondary nitrogen atoms and exocyclic carbon–oxygen double bonds (Law et al., 2004). The features are retained in the diaquamanganese(II) (Maistralis et al., 1991), dihydrated diaquairon(II) (Baran et al., 1996), triaquacobalt(II), triaquanickel(II) (Sun & Jin, 2004) and diaquacopper(II) (Luo et al., 2002) derivatives; the anion chelates to the metal atoms through the 5-carboxylato and 4-oxo oxygen atoms. The diaquamanganese (Maistralis et al., 1991), diaquacopper (Luo et al., 2002) and the present diaquacobalt(II) compounds are isostructural; two carboxylate monoanions chelate in this manner across a center of inversion. Hydrogen bonds link adjacent octahedral molecules into a three-dimensional network.