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Supporting information
![]() | Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536810007543/bq2195sup1.cif |
![]() | Structure factor file (CIF format) https://doi.org/10.1107/S1600536810007543/bq2195Isup2.hkl |
CCDC reference: 752400
Key indicators
- Single-crystal X-ray study
- T = 296 K
- Mean
(C-C) = 0.007 Å
- Disorder in main residue
- R factor = 0.025
- wR factor = 0.071
- Data-to-parameter ratio = 8.8
checkCIF/PLATON results
No syntax errors found
Alert level B PLAT420_ALERT_2_B D-H Without Acceptor >O8' - >H8'D ... ?
Alert level C PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X) Zn1 -- O5 .. 5.96 su PLAT341_ALERT_3_C Low Bond Precision on C-C Bonds (x 1000) Ang .. 7 PLAT915_ALERT_3_C Low Friedel Pair Coverage ...................... 67.80 Perc. PLAT480_ALERT_4_C Long H...A H-Bond Reported H9'C .. O2 .. 2.66 Ang.
Alert level G REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is correct. If it is not, please give the correct count in the _publ_section_exptl_refinement section of the submitted CIF. From the CIF: _diffrn_reflns_theta_max 25.00 From the CIF: _reflns_number_total 1296 Count of symmetry unique reflns 815 Completeness (_total/calc) 159.02% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 481 Fraction of Friedel pairs measured 0.590 Are heavy atom types Z>Si present yes PLAT301_ALERT_3_G Note: Main Residue Disorder ................... 3.00 Perc. PLAT720_ALERT_4_G Number of Unusual/Non-Standard Labels .......... 4 PLAT791_ALERT_4_G The Model has Chirality at C2 (Verify) .... R PLAT791_ALERT_4_G The Model has Chirality at C3 (Verify) .... R
0 ALERT level A = In general: serious problem 1 ALERT level B = Potentially serious problem 4 ALERT level C = Check and explain 5 ALERT level G = General alerts; check 0 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 3 ALERT type 3 Indicator that the structure quality may be low 5 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
Compound (I) was obtained at room temperature. An aqueous solution (5 ml) of L-tartaric acid (0.51 g, 3.4 mmol) was added dropwise into an aqueous solution (10 ml) of Zn(OAc)2˙2H2O (0.37 g, 1.7 mmol). White crystals were obtained in yield about 60% (based on Zn) after the solution was allowed to stand for several days. Elemental analysis, Found: C 17.36, H 3.23%. Calc. for C4H10O9Zn : calcd. C 17.94, H 3.74%.
All H atoms were positioned geometrically and treated as riding on their parent atoms, with C–H 0.980, O(aqua)–H 0.850, O(hydroxyl)–H 0.970 and with Uiso(H) = 1.2Ueq(C). The O8 and O9 atom is resolved into two positions by PART instructions. The geometries and anisotropic displacement parameters of disordered atoms were refined with soft restraints using the SHELXL commands damp.
Data collection: SMART (Sheldrick, 2008); cell refinement: SAINT (Sheldrick, 2008); data reduction: SAINT (Sheldrick, 2008); 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: SHELXL97 (Sheldrick, 2008).
[Zn(C4H4O6)(H2O)]·2H2O | F(000) = 544 |
Mr = 267.49 | Dx = 2.054 Mg m−3 |
Monoclinic, C2 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: C 2y | Cell parameters from 1296 reflections |
a = 12.8652 (16) Å | θ = 2.7–25.0° |
b = 8.7884 (14) Å | µ = 2.87 mm−1 |
c = 8.3816 (12) Å | T = 296 K |
β = 114.130 (1)° | Block, white |
V = 864.9 (2) Å3 | 0.50 × 0.48 × 0.45 mm |
Z = 4 |
Bruker SMART CCD area-detector diffractometer | 1296 independent reflections |
Radiation source: fine-focus sealed tube | 1262 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.017 |
phi and ω scans | θmax = 25.0°, θmin = 2.7° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −15→14 |
Tmin = 0.328, Tmax = 0.358 | k = −8→10 |
2182 measured reflections | l = −9→9 |
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)] = 0.025 | H-atom parameters constrained |
wR(F2) = 0.071 | w = 1/[σ2(Fo2) + (0.0392P)2 + 0.821P] where P = (Fo2 + 2Fc2)/3 |
S = 1.10 | (Δ/σ)max = 0.001 |
1296 reflections | Δρmax = 0.34 e Å−3 |
147 parameters | Δρmin = −0.42 e Å−3 |
1 restraint | Absolute structure: Flack (1983), 481 Friedel pairs |
Primary atom site location: structure-invariant direct methods | Absolute structure parameter: 0.01 (2) |
[Zn(C4H4O6)(H2O)]·2H2O | V = 864.9 (2) Å3 |
Mr = 267.49 | Z = 4 |
Monoclinic, C2 | Mo Kα radiation |
a = 12.8652 (16) Å | µ = 2.87 mm−1 |
b = 8.7884 (14) Å | T = 296 K |
c = 8.3816 (12) Å | 0.50 × 0.48 × 0.45 mm |
β = 114.130 (1)° |
Bruker SMART CCD area-detector diffractometer | 1296 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | 1262 reflections with I > 2σ(I) |
Tmin = 0.328, Tmax = 0.358 | Rint = 0.017 |
2182 measured reflections |
R[F2 > 2σ(F2)] = 0.025 | H-atom parameters constrained |
wR(F2) = 0.071 | Δρmax = 0.34 e Å−3 |
S = 1.10 | Δρmin = −0.42 e Å−3 |
1296 reflections | Absolute structure: Flack (1983), 481 Friedel pairs |
147 parameters | Absolute structure parameter: 0.01 (2) |
1 restraint |
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 | Occ. (<1) | |
Zn1 | 0.23251 (3) | 0.52758 (7) | 0.15818 (5) | 0.02164 (15) | |
O1 | 0.2031 (2) | 0.3568 (4) | 0.2954 (4) | 0.0271 (7) | |
O2 | 0.1296 (3) | 0.1272 (4) | 0.2844 (4) | 0.0418 (9) | |
O3 | 0.2105 (2) | 0.7016 (4) | −0.0093 (4) | 0.0289 (7) | |
O4 | 0.1403 (2) | 0.9327 (3) | −0.1022 (4) | 0.0307 (7) | |
O5 | 0.0911 (2) | 0.4067 (3) | −0.0441 (4) | 0.0270 (7) | |
H5 | 0.0531 | 0.4421 | −0.1579 | 0.032* | |
O6 | 0.0846 (2) | 0.6635 (4) | 0.1705 (4) | 0.0265 (7) | |
H6 | 0.0438 | 0.6340 | 0.2349 | 0.032* | |
O7 | 0.3436 (3) | 0.6376 (5) | 0.3781 (4) | 0.0447 (9) | |
H7B | 0.3339 | 0.6097 | 0.4681 | 0.054* | |
H7C | 0.3352 | 0.7335 | 0.3666 | 0.054* | |
O8 | 0.1503 (7) | 0.4516 (9) | 0.6526 (9) | 0.042 (3) | 0.499 (12) |
H8A | 0.0955 | 0.4991 | 0.5745 | 0.050* | 0.499 (12) |
H8D | 0.2121 | 0.5007 | 0.6784 | 0.050* | 0.499 (12) |
O9 | 0.0715 (6) | 0.8274 (9) | 0.4409 (8) | 0.038 (2) | 0.495 (11) |
H9A | 0.0955 | 0.8838 | 0.5312 | 0.057* | 0.495 (11) |
H9C | 0.0299 | 0.7572 | 0.4531 | 0.057* | 0.495 (11) |
O8' | 0.0611 (7) | 0.4189 (9) | 0.6283 (8) | 0.042 (3) | 0.501 (12) |
H8'A | −0.0075 | 0.3939 | 0.5660 | 0.050* | 0.501 (12) |
H8'D | 0.0751 | 0.5059 | 0.5974 | 0.050* | 0.501 (12) |
O9' | 0.1034 (6) | 0.6981 (9) | 0.4957 (8) | 0.038 (2) | 0.505 (11) |
H9'A | 0.0453 | 0.7453 | 0.4937 | 0.045* | 0.505 (11) |
H9'C | 0.1636 | 0.7473 | 0.5563 | 0.045* | 0.505 (11) |
C1 | 0.1372 (3) | 0.2489 (5) | 0.2135 (6) | 0.0242 (9) | |
C2 | 0.0635 (4) | 0.2672 (5) | 0.0178 (6) | 0.0213 (10) | |
H2 | 0.0786 | 0.1821 | −0.0453 | 0.026* | |
C3 | 0.0619 (4) | 0.8000 (5) | 0.0673 (6) | 0.0240 (11) | |
H3 | 0.0737 | 0.8879 | 0.1447 | 0.029* | |
C4 | 0.1442 (3) | 0.8113 (5) | −0.0218 (6) | 0.0233 (9) |
U11 | U22 | U33 | U12 | U13 | U23 | |
Zn1 | 0.0224 (2) | 0.0192 (2) | 0.0234 (2) | −0.0043 (2) | 0.00947 (16) | 0.0007 (2) |
O1 | 0.0278 (14) | 0.0253 (17) | 0.0275 (16) | −0.0077 (13) | 0.0104 (12) | 0.0035 (14) |
O2 | 0.070 (2) | 0.026 (2) | 0.0321 (18) | −0.0124 (17) | 0.0231 (17) | 0.0034 (15) |
O3 | 0.0307 (15) | 0.0190 (16) | 0.0466 (19) | 0.0052 (13) | 0.0257 (14) | 0.0091 (14) |
O4 | 0.0287 (14) | 0.0182 (18) | 0.0502 (19) | 0.0017 (13) | 0.0212 (14) | 0.0064 (15) |
O5 | 0.0375 (15) | 0.0179 (17) | 0.0333 (17) | −0.0090 (13) | 0.0224 (13) | −0.0027 (13) |
O6 | 0.0287 (14) | 0.0259 (17) | 0.0260 (15) | 0.0033 (12) | 0.0124 (12) | −0.0001 (12) |
O7 | 0.051 (2) | 0.048 (2) | 0.0279 (16) | −0.0214 (18) | 0.0087 (15) | −0.0063 (17) |
O8 | 0.050 (6) | 0.041 (5) | 0.030 (4) | −0.001 (3) | 0.012 (3) | 0.002 (3) |
O9 | 0.043 (4) | 0.044 (6) | 0.023 (4) | −0.007 (3) | 0.010 (3) | −0.007 (3) |
O8' | 0.050 (5) | 0.041 (4) | 0.029 (4) | −0.001 (4) | 0.012 (3) | 0.002 (3) |
O9' | 0.043 (4) | 0.044 (5) | 0.023 (4) | −0.007 (3) | 0.010 (3) | −0.008 (3) |
C1 | 0.0273 (19) | 0.023 (2) | 0.027 (2) | 0.0014 (18) | 0.0157 (17) | 0.0015 (18) |
C2 | 0.028 (2) | 0.014 (2) | 0.026 (2) | −0.0046 (17) | 0.0149 (18) | 0.0000 (18) |
C3 | 0.028 (2) | 0.012 (2) | 0.036 (3) | −0.0012 (18) | 0.017 (2) | −0.0045 (19) |
C4 | 0.0201 (18) | 0.017 (2) | 0.034 (2) | −0.0032 (15) | 0.0125 (17) | −0.0028 (18) |
Zn1—O3 | 2.016 (3) | O8—H8A | 0.8501 |
Zn1—O1 | 2.019 (3) | O8—H8D | 0.8500 |
Zn1—O4i | 2.054 (3) | O8—H8'D | 1.0056 |
Zn1—O7 | 2.054 (3) | O9—H9A | 0.8500 |
Zn1—O5 | 2.189 (3) | O9—H9C | 0.8500 |
Zn1—O6 | 2.285 (3) | O9—H9'A | 0.9764 |
O1—C1 | 1.270 (6) | O8'—H8A | 1.0296 |
O2—C1 | 1.247 (6) | O8'—H8'A | 0.8500 |
O3—C4 | 1.264 (5) | O8'—H8'D | 0.8500 |
O4—C4 | 1.252 (5) | O9'—H9'A | 0.8500 |
O4—Zn1ii | 2.054 (3) | O9'—H9'C | 0.8500 |
O5—C2 | 1.431 (5) | C1—C2 | 1.531 (6) |
O5—H5 | 0.9300 | C2—C2iii | 1.537 (9) |
O6—C3 | 1.437 (6) | C2—H2 | 0.9800 |
O6—H6 | 0.9300 | C3—C4 | 1.529 (6) |
O7—H7B | 0.8500 | C3—C3iii | 1.529 (10) |
O7—H7C | 0.8500 | C3—H3 | 0.9800 |
O3—Zn1—O1 | 162.78 (11) | H8D—O8—H8'D | 120.0 |
O3—Zn1—O4i | 92.67 (13) | H9A—O9—H9C | 109.5 |
O1—Zn1—O4i | 100.41 (13) | H9A—O9—H9'A | 95.4 |
O3—Zn1—O7 | 96.64 (15) | H9A—O9—H9'C | 77.2 |
O1—Zn1—O7 | 93.60 (14) | H9C—O9—H9'C | 87.0 |
O4i—Zn1—O7 | 93.97 (14) | H9'A—O9—H9'C | 70.2 |
O3—Zn1—O5 | 89.61 (13) | H8A—O8'—H8'A | 115.6 |
O1—Zn1—O5 | 77.90 (12) | H8'A—O8'—H8'D | 110.0 |
O4i—Zn1—O5 | 96.51 (12) | H9C—O9'—H9'C | 116.2 |
O7—Zn1—O5 | 167.53 (13) | H9'A—O9'—H9'C | 110.0 |
O3—Zn1—O6 | 75.68 (11) | O2—C1—O1 | 123.2 (4) |
O1—Zn1—O6 | 90.55 (12) | O2—C1—C2 | 117.8 (4) |
O4i—Zn1—O6 | 168.07 (12) | O1—C1—C2 | 119.0 (4) |
O7—Zn1—O6 | 90.00 (14) | O5—C2—C1 | 110.0 (4) |
O5—Zn1—O6 | 81.09 (11) | O5—C2—C2iii | 109.4 (3) |
C1—O1—Zn1 | 119.1 (3) | C1—C2—C2iii | 110.6 (5) |
C4—O3—Zn1 | 122.3 (3) | O5—C2—H2 | 109.0 |
C4—O4—Zn1ii | 127.5 (3) | C1—C2—H2 | 109.0 |
C2—O5—Zn1 | 112.7 (3) | C2iii—C2—H2 | 109.0 |
C2—O5—H5 | 123.7 | O6—C3—C4 | 109.7 (4) |
Zn1—O5—H5 | 123.7 | O6—C3—C3iii | 109.8 (3) |
C3—O6—Zn1 | 112.2 (3) | C4—C3—C3iii | 111.1 (5) |
C3—O6—H6 | 123.9 | O6—C3—H3 | 108.7 |
Zn1—O6—H6 | 123.9 | C4—C3—H3 | 108.7 |
Zn1—O7—H7B | 111.1 | C3iii—C3—H3 | 108.7 |
Zn1—O7—H7C | 110.8 | O4—C4—O3 | 124.9 (4) |
H7B—O7—H7C | 109.2 | O4—C4—C3 | 115.8 (4) |
H8A—O8—H8D | 110.0 | O3—C4—C3 | 119.3 (4) |
Symmetry codes: (i) −x+1/2, y−1/2, −z; (ii) −x+1/2, y+1/2, −z; (iii) −x, y, −z. |
D—H···A | D—H | H···A | D···A | D—H···A |
O8—H8D···O2iv | 0.85 | 2.23 | 3.074 (10) | 174 |
O9—H9A···O1iv | 0.85 | 2.41 | 2.849 (7) | 113 |
O9—H9A···O7iv | 0.85 | 2.38 | 3.094 (8) | 142 |
O9—H9C···O9v | 0.85 | 1.95 | 2.421 (14) | 113 |
O8—H8A···O8′v | 0.85 | 2.16 | 2.791 (12) | 131 |
O9—H9C···O9′v | 0.85 | 2.00 | 2.761 (10) | 149 |
O9′—H9′C···O1iv | 0.85 | 1.92 | 2.765 (7) | 177 |
O9′—H9′C···O2iv | 0.85 | 2.66 | 3.225 (8) | 125 |
Symmetry codes: (iv) −x+1/2, y+1/2, −z+1; (v) −x, y, −z+1. |
Experimental details
Crystal data | |
Chemical formula | [Zn(C4H4O6)(H2O)]·2H2O |
Mr | 267.49 |
Crystal system, space group | Monoclinic, C2 |
Temperature (K) | 296 |
a, b, c (Å) | 12.8652 (16), 8.7884 (14), 8.3816 (12) |
β (°) | 114.130 (1) |
V (Å3) | 864.9 (2) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 2.87 |
Crystal size (mm) | 0.50 × 0.48 × 0.45 |
Data collection | |
Diffractometer | Bruker SMART CCD area-detector diffractometer |
Absorption correction | Multi-scan (SADABS; Sheldrick, 1996) |
Tmin, Tmax | 0.328, 0.358 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 2182, 1296, 1262 |
Rint | 0.017 |
(sin θ/λ)max (Å−1) | 0.595 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.025, 0.071, 1.10 |
No. of reflections | 1296 |
No. of parameters | 147 |
No. of restraints | 1 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.34, −0.42 |
Absolute structure | Flack (1983), 481 Friedel pairs |
Absolute structure parameter | 0.01 (2) |
Computer programs: SMART (Sheldrick, 2008), SAINT (Sheldrick, 2008), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).
D—H···A | D—H | H···A | D···A | D—H···A |
O8—H8D···O2i | 0.85 | 2.23 | 3.074 (10) | 173.8 |
O9—H9A···O1i | 0.85 | 2.41 | 2.849 (7) | 112.9 |
O9—H9A···O7i | 0.85 | 2.38 | 3.094 (8) | 141.5 |
O9—H9C···O9ii | 0.85 | 1.95 | 2.421 (14) | 113.4 |
O8—H8A···O8'ii | 0.85 | 2.16 | 2.791 (12) | 131.4 |
O9—H9C···O9'ii | 0.85 | 2.00 | 2.761 (10) | 148.5 |
O9'—H9'C···O1i | 0.85 | 1.92 | 2.765 (7) | 176.6 |
O9'—H9'C···O2i | 0.85 | 2.66 | 3.225 (8) | 125.3 |
Symmetry codes: (i) −x+1/2, y+1/2, −z+1; (ii) −x, y, −z+1. |
Chiral inorganic-organic materials have received much attention, not only because of their numerous potential applications in nonlinear optics, enantioselective catalysis and medicine, but also owing to their intriguing variety of architectures and topologies (Ma et al., 2007; Kitagawa et al., 2004; Lee et al., 2002). L-tartaric acid, a simple and inexpensive chiral ligand source, was often used to construct novel chiral multifunctional materials (Liu et al., 2008; Gelbrich et al., 2006). Firstly, tartaric acid is flexible dicarboxylate ligands with two hydroxyl groups, and can offer more coordination sites and allow the formation of five- or six-membered ring, which can stabilize the solid network. Secondly, the deprotonated carboxylate group possesses polarizable system, it can transfer electrons easily. So, tartrate ligand is a good candidate of constructing chiral magnetic and chiral optical materials. In this paper, we reported the structure of the title compound, which is constructed by the chiral L-tartrate ligand.
X-ray single crystal diffraction studies reveal that the crystallographic unique unit of (I) is composed of one ZnII ion, two halves of L-tartrate ligand, one coordination water and two disordered lattice water molecules with occupancies both in the 0.5:0.5 ratio. As shown in Fig. 1, two kinds of L-tart ligands chelate two Zn centers through the hydroxyl and carboxylate groups in cis confirmation to form [Zn2(L-tart)2] dimmer, which is similar to the reported tartrate salts (Coronado et al., 2006). And, the octahedral geometry of ZnII is completed by one unchelating carboxylate oxygen atom and one water molecule. For compound (I), L-tartrate ligands adopt µ4- and µ2- two coordination modes, which link the [Zn2(L-tart)2] dimmers to form two-dimensional coordination layer. The coordination and lattice water molecules hydrogen bond to the hydroxy and carboxylate groups, so the two-dimensional coordination layers are further linked together to form three-dimensional supramolecular network (shown in Fig. 2). The parameters of hydrogen bonds are listed in Table 1.