Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807038743/bi2221sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807038743/bi2221Isup2.hkl |
CCDC reference: 1101494
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.006 Å
- R factor = 0.040
- wR factor = 0.106
- Data-to-parameter ratio = 11.1
checkCIF/PLATON results
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Alert level C PLAT041_ALERT_1_C Calc. and Rep. SumFormula Strings Differ .... ? PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ? PLAT045_ALERT_1_C Calculated and Reported Z Differ by ............ 2.00 Ratio PLAT062_ALERT_4_C Rescale T(min) & T(max) by ..................... 0.96 PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for O3 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for Fe1 PLAT480_ALERT_4_C Long H...A H-Bond Reported H2W .. O2 .. 2.78 Ang. PLAT482_ALERT_4_C Small D-H..A Angle Rep for O5 .. O2 .. 99.00 Deg. PLAT764_ALERT_4_C Overcomplete CIF Bond List Detected (Rep/Expd) . 1.20 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 PLAT794_ALERT_5_G Check Predicted Bond Valency for Fe1 (9) 1.69 PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints ....... 3
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 9 ALERT level C = Check and explain 4 ALERT level G = General alerts; check 5 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 2 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 4 ALERT type 4 Improvement, methodology, query or suggestion 1 ALERT type 5 Informative message, check
For the isostructural analogues, see: CoII (Delgado et al., 2003); NiII (Liu et al., 2005); ZnII (Zhang et al., 2003; Delgado et al., 2003); CdII (Mao et al., 2004).
A mixture of FeSO4 (0.5 mmol), malonic acid (0.5 mmol), NaOH (1 mmol), pyrazine (1 mmol) and H2O (8 ml) in a 25 ml Teflon-lined stainless steel autoclave was heated at 443 K for two days, and then cooled to room temperature. Light green block crystals of the title compound were obtained with a yield of 22%. Elemental analysis: calculated C 27.91, H 2.79, N 6.51%; found: C 27.88, H 2.75, N 6.47%.
All H atoms on C atoms were generated geometrically and refined as riding atoms with C—H = 0.93 or 0.97 Å and with Uiso(H) = 1.2Ueq(C). The H atoms of the water molecule were located from difference Fourier maps and were refined with distance restraints of d(H—H) = 1.38 (2) Å, d(O—H) = 0.82 (1) Å.
The title compound is isostructural with its CoII (Delgado et al., 2003), NiII (Liu et al., 2005), ZnII (Zhang et al., 2003; Delgado et al., 2003) and CdII (Mao et al., 2004) analogues. The FeII atom exhibits sixfold coordination, chelated by two O atoms from one malonate ligand to form a six-membered boat-type ring, and by two O atoms from two neighbouring malonates, one water molecule and one N atom from the bridging pyrazine ligand (Fig. 1). The Fe—O(carboxylate) and Fe—N bond lengths are in the range 2.064 (4)–2.202 (4) and 2.272 (4) Å, respectively.
The [Fe(malonate)(H2O)] units form two-dimensional networks parallel to the (010) planes. These are linked by the bridging pyrazine ligands into a three-dimensional structure. O—H···O hydrogen bonds (Table 1) are formed between the coordinated water molecules and the malonate ligands.
For the isostructural analogues, see: CoII (Delgado et al., 2003); NiII (Liu et al., 2005); ZnII (Zhang et al., 2003; Delgado et al., 2003); CdII (Mao et al., 2004).
Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT-Plus (Bruker, 2001); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 2001); software used to prepare material for publication: SHELXTL.
[Fe2(C3H2O4)2(C4H4N2)(H2O)2] | F(000) = 436 |
Mr = 431.92 | Dx = 1.930 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2yn | Cell parameters from 1293 reflections |
a = 6.9652 (10) Å | θ = 2.8–25.0° |
b = 14.589 (2) Å | µ = 2.01 mm−1 |
c = 7.3212 (10) Å | T = 293 K |
β = 92.179 (1)° | Block, green |
V = 743.39 (18) Å3 | 0.36 × 0.28 × 0.24 mm |
Z = 2 |
Bruker APEXII CCD diffractometer | 1293 independent reflections |
Radiation source: fine-focus sealed tube | 1100 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.023 |
φ and ω scans | θmax = 25.0°, θmin = 2.8° |
Absorption correction: multi-scan (SADABS; Bruker, 2001) | h = −8→3 |
Tmin = 0.532, Tmax = 0.644 | k = −13→16 |
2391 measured reflections | l = −8→8 |
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)] = 0.040 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.106 | w = 1/[σ2(Fo2) + (0.0653P)2 + 1.1979P] where P = (Fo2 + 2Fc2)/3 |
S = 1.00 | (Δ/σ)max = 0.010 |
1293 reflections | Δρmax = 0.65 e Å−3 |
116 parameters | Δρmin = −0.40 e Å−3 |
3 restraints | Extinction correction: SHELXL97 (Sheldrick, 1997), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.039 (4) |
[Fe2(C3H2O4)2(C4H4N2)(H2O)2] | V = 743.39 (18) Å3 |
Mr = 431.92 | Z = 2 |
Monoclinic, P21/n | Mo Kα radiation |
a = 6.9652 (10) Å | µ = 2.01 mm−1 |
b = 14.589 (2) Å | T = 293 K |
c = 7.3212 (10) Å | 0.36 × 0.28 × 0.24 mm |
β = 92.179 (1)° |
Bruker APEXII CCD diffractometer | 1293 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 2001) | 1100 reflections with I > 2σ(I) |
Tmin = 0.532, Tmax = 0.644 | Rint = 0.023 |
2391 measured reflections |
R[F2 > 2σ(F2)] = 0.040 | 3 restraints |
wR(F2) = 0.106 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.00 | Δρmax = 0.65 e Å−3 |
1293 reflections | Δρmin = −0.40 e Å−3 |
116 parameters |
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 | ||
C1 | 0.5845 (6) | 0.3316 (3) | 0.7563 (6) | 0.0316 (9) | |
C2 | 0.6129 (7) | 0.3912 (3) | 0.5893 (6) | 0.0397 (10) | |
H2A | 0.5238 | 0.4423 | 0.5912 | 0.048* | |
H2B | 0.7422 | 0.4160 | 0.5955 | 0.048* | |
C3 | 0.5827 (6) | 0.3401 (3) | 0.4125 (6) | 0.0317 (9) | |
C4 | 0.4533 (7) | 0.0742 (3) | 0.5913 (7) | 0.0473 (12) | |
H4 | 0.4138 | 0.1251 | 0.6565 | 0.057* | |
C5 | 0.6788 (6) | −0.0045 (3) | 0.4450 (7) | 0.0437 (11) | |
H5 | 0.8030 | −0.0107 | 0.4042 | 0.052* | |
Fe1 | 0.83758 (7) | 0.19136 (3) | 0.58103 (6) | 0.0177 (3) | |
N1 | 0.6323 (5) | 0.0716 (2) | 0.5376 (5) | 0.0357 (8) | |
O1 | 0.6634 (4) | 0.2528 (2) | 0.7697 (4) | 0.0397 (8) | |
O2 | 0.4864 (4) | 0.3672 (2) | 0.8748 (4) | 0.0403 (8) | |
O3 | 0.6700 (5) | 0.2644 (2) | 0.3900 (4) | 0.0429 (8) | |
O4 | 0.4752 (4) | 0.3774 (2) | 0.2946 (4) | 0.0393 (7) | |
O5 | 1.0315 (5) | 0.3106 (2) | 0.5861 (4) | 0.0439 (8) | |
H2W | 1.090 (8) | 0.308 (4) | 0.490 (4) | 0.080* | |
H1W | 1.101 (7) | 0.298 (4) | 0.677 (5) | 0.080* |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.034 (2) | 0.029 (2) | 0.032 (2) | 0.0001 (18) | 0.0005 (16) | −0.0053 (18) |
C2 | 0.056 (3) | 0.034 (2) | 0.029 (2) | 0.005 (2) | 0.0022 (19) | 0.0010 (19) |
C3 | 0.036 (2) | 0.028 (2) | 0.032 (2) | 0.0035 (18) | 0.0042 (17) | 0.0045 (18) |
C4 | 0.044 (3) | 0.039 (3) | 0.060 (3) | −0.005 (2) | 0.018 (2) | −0.014 (2) |
C5 | 0.038 (2) | 0.034 (3) | 0.060 (3) | −0.002 (2) | 0.012 (2) | −0.009 (2) |
Fe1 | 0.0219 (3) | 0.0169 (4) | 0.0145 (3) | 0.00068 (19) | 0.0018 (2) | −0.00062 (19) |
N1 | 0.0357 (18) | 0.033 (2) | 0.038 (2) | −0.0020 (16) | 0.0017 (15) | −0.0011 (16) |
O1 | 0.0516 (18) | 0.0358 (18) | 0.0325 (16) | 0.0069 (14) | 0.0116 (13) | 0.0027 (13) |
O2 | 0.0454 (17) | 0.0379 (18) | 0.0387 (17) | 0.0043 (14) | 0.0168 (13) | 0.0000 (14) |
O3 | 0.054 (2) | 0.042 (2) | 0.0325 (16) | 0.0114 (15) | −0.0052 (14) | −0.0031 (14) |
O4 | 0.0476 (17) | 0.0335 (17) | 0.0363 (16) | 0.0027 (14) | −0.0060 (13) | 0.0027 (14) |
O5 | 0.0467 (19) | 0.053 (2) | 0.0325 (17) | −0.0013 (15) | 0.0019 (14) | 0.0000 (15) |
C1—O2 | 1.239 (5) | C5—C4i | 1.390 (7) |
C1—O1 | 1.276 (5) | C5—H5 | 0.930 |
C1—C2 | 1.519 (6) | Fe1—O2ii | 2.050 (3) |
C2—C3 | 1.501 (6) | Fe1—O4iii | 2.064 (3) |
C2—H2A | 0.970 | Fe1—O1 | 2.076 (3) |
C2—H2B | 0.970 | Fe1—O3 | 2.081 (3) |
C3—O4 | 1.246 (5) | Fe1—O5 | 2.202 (4) |
C3—O3 | 1.275 (6) | Fe1—N1 | 2.272 (4) |
C4—N1 | 1.322 (6) | O2—Fe1iv | 2.050 (3) |
C4—C5i | 1.390 (7) | O4—Fe1v | 2.064 (3) |
C4—H4 | 0.930 | O5—H2W | 0.83 (4) |
C5—N1 | 1.347 (6) | O5—H1W | 0.83 (4) |
O2—C1—O1 | 124.8 (4) | O4iii—Fe1—O3 | 172.32 (12) |
O2—C1—C2 | 114.6 (4) | O1—Fe1—O3 | 84.20 (12) |
O1—C1—C2 | 120.6 (4) | O2ii—Fe1—O5 | 90.84 (12) |
C3—C2—C1 | 113.1 (4) | O4iii—Fe1—O5 | 95.99 (12) |
C3—C2—H2A | 109.0 | O1—Fe1—O5 | 91.21 (12) |
C1—C2—H2A | 109.0 | O3—Fe1—O5 | 86.27 (14) |
C3—C2—H2B | 109.0 | O2ii—Fe1—N1 | 84.81 (12) |
C1—C2—H2B | 109.0 | O4iii—Fe1—N1 | 90.23 (13) |
H2A—C2—H2B | 107.8 | O1—Fe1—N1 | 92.56 (13) |
O4—C3—O3 | 124.5 (4) | O3—Fe1—N1 | 88.03 (13) |
O4—C3—C2 | 116.2 (4) | O5—Fe1—N1 | 172.81 (13) |
O3—C3—C2 | 119.3 (4) | C4—N1—C5 | 114.9 (4) |
N1—C4—C5i | 123.2 (4) | C4—N1—Fe1 | 122.1 (3) |
N1—C4—H4 | 118.4 | C5—N1—Fe1 | 122.9 (3) |
C5i—C4—H4 | 118.4 | C1—O1—Fe1 | 126.8 (3) |
N1—C5—C4i | 122.0 (4) | C1—O2—Fe1iv | 130.5 (3) |
N1—C5—H5 | 119.0 | C3—O3—Fe1 | 128.0 (3) |
C4i—C5—H5 | 119.0 | C3—O4—Fe1v | 124.2 (3) |
O2ii—Fe1—O4iii | 97.03 (13) | Fe1—O5—H2W | 106 (4) |
O2ii—Fe1—O1 | 173.95 (12) | Fe1—O5—H1W | 100 (5) |
O4iii—Fe1—O1 | 88.42 (13) | H2W—O5—H1W | 113 (3) |
O2ii—Fe1—O3 | 90.26 (13) |
Symmetry codes: (i) −x+1, −y, −z+1; (ii) x+1/2, −y+1/2, z−1/2; (iii) x+1/2, −y+1/2, z+1/2; (iv) x−1/2, −y+1/2, z+1/2; (v) x−1/2, −y+1/2, z−1/2. |
D—H···A | D—H | H···A | D···A | D—H···A |
O5—H2W···O1ii | 0.83 (4) | 1.93 (3) | 2.689 (4) | 152 (6) |
O5—H2W···O2ii | 0.83 (4) | 2.78 (6) | 3.031 (5) | 99 (5) |
Symmetry code: (ii) x+1/2, −y+1/2, z−1/2. |
Experimental details
Crystal data | |
Chemical formula | [Fe2(C3H2O4)2(C4H4N2)(H2O)2] |
Mr | 431.92 |
Crystal system, space group | Monoclinic, P21/n |
Temperature (K) | 293 |
a, b, c (Å) | 6.9652 (10), 14.589 (2), 7.3212 (10) |
β (°) | 92.179 (1) |
V (Å3) | 743.39 (18) |
Z | 2 |
Radiation type | Mo Kα |
µ (mm−1) | 2.01 |
Crystal size (mm) | 0.36 × 0.28 × 0.24 |
Data collection | |
Diffractometer | Bruker APEXII CCD |
Absorption correction | Multi-scan (SADABS; Bruker, 2001) |
Tmin, Tmax | 0.532, 0.644 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 2391, 1293, 1100 |
Rint | 0.023 |
(sin θ/λ)max (Å−1) | 0.595 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.040, 0.106, 1.00 |
No. of reflections | 1293 |
No. of parameters | 116 |
No. of restraints | 3 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.65, −0.40 |
Computer programs: APEX2 (Bruker, 2004), SAINT-Plus (Bruker, 2001), SAINT-Plus, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL (Bruker, 2001), SHELXTL.
D—H···A | D—H | H···A | D···A | D—H···A |
O5—H2W···O1i | 0.83 (4) | 1.93 (3) | 2.689 (4) | 152 (6) |
O5—H2W···O2i | 0.83 (4) | 2.78 (6) | 3.031 (5) | 99 (5) |
Symmetry code: (i) x+1/2, −y+1/2, z−1/2. |
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The title compound is isostructural with its CoII (Delgado et al., 2003), NiII (Liu et al., 2005), ZnII (Zhang et al., 2003; Delgado et al., 2003) and CdII (Mao et al., 2004) analogues. The FeII atom exhibits sixfold coordination, chelated by two O atoms from one malonate ligand to form a six-membered boat-type ring, and by two O atoms from two neighbouring malonates, one water molecule and one N atom from the bridging pyrazine ligand (Fig. 1). The Fe—O(carboxylate) and Fe—N bond lengths are in the range 2.064 (4)–2.202 (4) and 2.272 (4) Å, respectively.
The [Fe(malonate)(H2O)] units form two-dimensional networks parallel to the (010) planes. These are linked by the bridging pyrazine ligands into a three-dimensional structure. O—H···O hydrogen bonds (Table 1) are formed between the coordinated water molecules and the malonate ligands.