metal-organic compounds
The title compound, [Zn2(C9H6O5)2(C5H5N)2], contains pairs of pyridine-coordinated Zn2+ ions [ZnZn = 2.987 (1) Å] which are bridged by two carboxylate fragments and two –O–CH2–CO2 fragments of four 4-carboxylatophenoxyacetate dianions to give rise to ZnO4N square-based pyramids. The extended connectivity results in a layered structure.
Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805031788/hb6279sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536805031788/hb6279Isup2.hkl |
CCDC reference: 289753
Computing details top
Data collection: RAPID-AUTO (Rigaku, 1998); cell refinement: RAPID-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPII (Johnson, 1976); software used to prepare material for publication: SHELXL97.
Crystal data top
[Zn2(C9H6O5)2(C5H5N)2] | F(000) = 688 |
Mr = 677.22 | Dx = 1.677 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 12595 reflections |
a = 9.354 (2) Å | θ = 3.5–27.5° |
b = 14.876 (3) Å | µ = 1.85 mm−1 |
c = 10.231 (2) Å | T = 295 K |
β = 109.58 (3)° | Block, colorless |
V = 1341.3 (5) Å3 | 0.34 × 0.25 × 0.16 mm |
Z = 2 |
Data collection top
Rigaku RAXIS-RAPID diffractometer | 3069 independent reflections |
Radiation source: fine-focus sealed tube | 2553 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.026 |
Detector resolution: 10 pixels mm-1 | θmax = 27.5°, θmin = 3.5° |
ω scan | h = −12→12 |
Absorption correction: multi-scan (ABSCOR; Higashi, 1995) | k = −19→19 |
Tmin = 0.459, Tmax = 0.756 | l = −12→13 |
12817 measured reflections |
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)] = 0.032 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.080 | H-atom parameters constrained |
S = 1.04 | w = 1/[σ2(Fo2) + (0.0461P)2 + 0.5185P] where P = (Fo2 + 2Fc2)/3 |
3069 reflections | (Δ/σ)max = 0.001 |
190 parameters | Δρmax = 0.64 e Å−3 |
0 restraints | Δρmin = −0.26 e Å−3 |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
x | y | z | Uiso*/Ueq | ||
Zn1 | 0.38247 (3) | 0.47092 (2) | 0.36770 (2) | 0.0300 (1) | |
O1 | 0.5176 (2) | 0.3637 (1) | 0.4570 (2) | 0.0425 (4) | |
O2 | 0.6949 (2) | 0.4019 (1) | 0.6569 (2) | 0.0441 (4) | |
O3 | 0.7574 (2) | −0.0237 (1) | 0.6673 (2) | 0.0402 (4) | |
O4 | 0.7504 (2) | −0.0545 (1) | 1.0117 (2) | 0.0440 (4) | |
O5 | 0.5660 (2) | −0.0175 (1) | 0.8144 (2) | 0.0411 (4) | |
N1 | 0.2647 (2) | 0.4023 (1) | 0.1931 (2) | 0.0312 (4) | |
C1 | 0.1163 (3) | 0.4094 (2) | 0.1328 (3) | 0.064 (1) | |
C2 | 0.0357 (3) | 0.3568 (3) | 0.0228 (4) | 0.099 (2) | |
C3 | 0.1128 (3) | 0.2933 (2) | −0.0271 (3) | 0.067 (1) | |
C4 | 0.2647 (3) | 0.2868 (2) | 0.0319 (3) | 0.044 (1) | |
C5 | 0.3372 (3) | 0.3426 (2) | 0.1411 (2) | 0.039 (1) | |
C6 | 0.6247 (3) | 0.3454 (1) | 0.5662 (2) | 0.034 (1) | |
C7 | 0.6682 (2) | 0.2484 (1) | 0.5919 (2) | 0.029 (1) | |
C8 | 0.6153 (3) | 0.1841 (1) | 0.4878 (2) | 0.033 (1) | |
C9 | 0.6477 (3) | 0.0939 (2) | 0.5160 (2) | 0.034 (1) | |
C10 | 0.7326 (2) | 0.0670 (1) | 0.6493 (2) | 0.031 (1) | |
C11 | 0.7869 (3) | 0.1301 (2) | 0.7542 (2) | 0.036 (1) | |
C12 | 0.7544 (2) | 0.2205 (1) | 0.7240 (2) | 0.034 (1) | |
C13 | 0.8096 (3) | −0.0568 (2) | 0.8055 (3) | 0.042 (1) | |
C14 | 0.6975 (3) | −0.0409 (1) | 0.8832 (2) | 0.034 (1) | |
H1 | 0.0643 | 0.4518 | 0.1664 | 0.077* | |
H2 | −0.0688 | 0.3636 | −0.0175 | 0.119* | |
H3 | 0.0605 | 0.2558 | −0.1002 | 0.080* | |
H4 | 0.3193 | 0.2454 | −0.0007 | 0.053* | |
H5 | 0.4421 | 0.3384 | 0.1806 | 0.047* | |
H8 | 0.5577 | 0.2019 | 0.3986 | 0.039* | |
H9 | 0.6126 | 0.0514 | 0.4458 | 0.040* | |
H11 | 0.8442 | 0.1122 | 0.8435 | 0.043* | |
H12 | 0.7913 | 0.2630 | 0.7938 | 0.041* | |
H13a | 0.9051 | −0.0278 | 0.8560 | 0.050* | |
H13b | 0.8285 | −0.1208 | 0.8036 | 0.050* |
Atomic displacement parameters (Å2) top
U11 | U22 | U33 | U12 | U13 | U23 | |
Zn1 | 0.0351 (2) | 0.0248 (1) | 0.0267 (1) | −0.0011 (1) | 0.0059 (1) | −0.0024 (1) |
O1 | 0.050 (1) | 0.034 (1) | 0.040 (1) | 0.010 (1) | 0.010 (1) | 0.008 (1) |
O2 | 0.044 (1) | 0.026 (1) | 0.057 (1) | 0.002 (1) | 0.009 (1) | −0.003 (1) |
O3 | 0.062 (1) | 0.027 (1) | 0.038 (1) | 0.011 (1) | 0.026 (1) | 0.005 (1) |
O4 | 0.053 (1) | 0.047 (1) | 0.036 (1) | 0.005 (1) | 0.019 (1) | 0.005 (1) |
O5 | 0.044 (1) | 0.041 (1) | 0.042 (1) | 0.006 (1) | 0.019 (1) | 0.001 (1) |
N1 | 0.031 (1) | 0.030 (1) | 0.032 (1) | −0.002 (1) | 0.011 (1) | −0.005 (1) |
C1 | 0.032 (1) | 0.085 (2) | 0.073 (2) | 0.002 (1) | 0.014 (1) | −0.043 (2) |
C2 | 0.025 (1) | 0.151 (4) | 0.109 (3) | −0.010 (2) | 0.007 (2) | −0.085 (3) |
C3 | 0.044 (2) | 0.084 (2) | 0.072 (2) | −0.022 (2) | 0.020 (2) | −0.0505 (18) |
C4 | 0.045 (1) | 0.039 (1) | 0.049 (1) | −0.002 (1) | 0.018 (1) | −0.014 (1) |
C5 | 0.032 (1) | 0.042 (1) | 0.039 (1) | 0.002 (1) | 0.007 (1) | −0.009 (1) |
C6 | 0.035 (1) | 0.028 (1) | 0.042 (1) | 0.002 (1) | 0.018 (1) | 0.005 (1) |
C7 | 0.029 (1) | 0.026 (1) | 0.034 (1) | 0.000 (1) | 0.011 (1) | 0.002 (1) |
C8 | 0.036 (1) | 0.035 (1) | 0.026 (1) | 0.001 (1) | 0.010 (1) | 0.003 (1) |
C9 | 0.043 (1) | 0.031 (1) | 0.030 (1) | −0.001 (1) | 0.016 (1) | −0.004 (1) |
C10 | 0.036 (1) | 0.027 (1) | 0.035 (1) | 0.004 (1) | 0.018 (1) | 0.003 (1) |
C11 | 0.039 (1) | 0.036 (1) | 0.029 (1) | 0.004 (1) | 0.006 (1) | 0.003 (1) |
C12 | 0.034 (1) | 0.031 (1) | 0.034 (1) | −0.002 (1) | 0.006 (1) | −0.006 (1) |
C13 | 0.056 (2) | 0.032 (1) | 0.043 (1) | 0.016 (1) | 0.025 (1) | 0.011 (1) |
C14 | 0.046 (1) | 0.023 (1) | 0.036 (1) | 0.002 (1) | 0.019 (1) | 0.002 (1) |
Geometric parameters (Å, º) top
Zn1—O1 | 2.051 (2) | C7—C12 | 1.385 (3) |
Zn1—O2i | 2.011 (2) | C7—C8 | 1.394 (3) |
Zn1—O4ii | 2.059 (2) | C8—C9 | 1.385 (3) |
Zn1—O5iii | 2.087 (2) | C9—C10 | 1.387 (3) |
Zn1—N1 | 2.032 (2) | C10—C11 | 1.388 (3) |
Zn1—Zn1i | 2.987 (1) | C11—C12 | 1.390 (3) |
O1—C6 | 1.255 (3) | C13—C14 | 1.532 (3) |
O2—C6 | 1.261 (3) | C1—H1 | 0.93 |
O3—C10 | 1.371 (2) | C2—H2 | 0.93 |
O3—C13 | 1.421 (3) | C3—H3 | 0.93 |
O4—C14 | 1.256 (3) | C4—H4 | 0.93 |
O5—C14 | 1.244 (3) | C5—H5 | 0.93 |
N1—C1 | 1.321 (3) | C8—H8 | 0.93 |
N1—C5 | 1.332 (3) | C9—H9 | 0.93 |
C1—C2 | 1.370 (4) | C11—H11 | 0.93 |
C2—C3 | 1.386 (4) | C12—H12 | 0.93 |
C3—C4 | 1.348 (4) | C13—H13a | 0.97 |
C4—C5 | 1.374 (3) | C13—H13b | 0.97 |
C6—C7 | 1.498 (3) | ||
O1—Zn1—O2i | 158.45 (7) | C9—C8—C7 | 120.6 (2) |
O1—Zn1—O4ii | 89.76 (7) | C10—C9—C8 | 119.8 (2) |
O1—Zn1—O5iii | 86.35 (7) | O3—C10—C9 | 115.5 (2) |
O1—Zn1—N1 | 94.17 (7) | O3—C10—C11 | 124.1 (2) |
O2i—Zn1—O4ii | 89.07 (7) | C9—C10—C11 | 120.4 (2) |
O2i—Zn1—O5iii | 87.03 (7) | C10—C11—C12 | 119.1 (2) |
O2i—Zn1—N1 | 107.22 (8) | C7—C12—C11 | 121.3 (2) |
O4ii—Zn1—O5iii | 158.88 (7) | O3—C13—C14 | 113.4 (2) |
O4ii—Zn1—N1 | 100.16 (7) | O5—C14—O4 | 127.3 (2) |
O5iii—Zn1—N1 | 100.82 (7) | O5—C14—C13 | 117.9 (2) |
O2i—Zn1—Zn1i | 88.03 (5) | O4—C14—C13 | 114.8 (2) |
N1—Zn1—Zn1i | 163.74 (5) | N1—C1—H1 | 118.6 |
O1—Zn1—Zn1i | 70.42 (5) | C2—C1—H1 | 118.6 |
O4ii—Zn1—Zn1i | 85.36 (5) | C1—C2—H2 | 120.6 |
O5iii—Zn1—Zn1i | 73.77 (5) | C3—C2—H2 | 120.6 |
C6—O1—Zn1 | 138.9 (2) | C4—C3—H3 | 120.5 |
C6—O2—Zn1i | 117.3 (2) | C2—C3—H3 | 120.5 |
C10—O3—C13 | 117.4 (2) | C3—C4—H4 | 120.7 |
C14—O4—Zn1iv | 119.4 (2) | C5—C4—H4 | 120.7 |
C14—O5—Zn1v | 133.5 (2) | N1—C5—H5 | 118.3 |
C1—N1—C5 | 117.5 (2) | C4—C5—H5 | 118.3 |
C1—N1—Zn1 | 123.1 (2) | C9—C8—H8 | 119.7 |
C5—N1—Zn1 | 119.2 (2) | C7—C8—H8 | 119.7 |
N1—C1—C2 | 122.8 (3) | C10—C9—H9 | 120.1 |
C1—C2—C3 | 118.7 (3) | C8—C9—H9 | 120.1 |
C4—C3—C2 | 119.0 (2) | C10—C11—H11 | 120.5 |
C3—C4—C5 | 118.6 (2) | C12—C11—H11 | 120.5 |
N1—C5—C4 | 123.3 (2) | C7—C12—H12 | 119.3 |
O1—C6—O2 | 125.0 (2) | C11—C12—H12 | 119.3 |
O1—C6—C7 | 117.0 (2) | O3—C13—H13a | 108.9 |
O2—C6—C7 | 117.9 (2) | C14—C13—H13a | 108.9 |
C12—C7—C8 | 118.7 (2) | O3—C13—H13b | 108.9 |
C12—C7—C6 | 119.7 (2) | C14—C13—H13b | 108.9 |
C8—C7—C6 | 121.4 (2) | H13a—C13—H13b | 107.7 |
O2i—Zn1—O1—C6 | 6.3 (4) | Zn1i—O2—C6—O1 | 5.5 (3) |
N1—Zn1—O1—C6 | 179.3 (2) | Zn1i—O2—C6—C7 | −172.5 (1) |
O4ii—Zn1—O1—C6 | −80.5 (2) | O1—C6—C7—C12 | −162.6 (2) |
O5iii—Zn1—O1—C6 | 78.7 (2) | O2—C6—C7—C12 | 15.5 (3) |
Zn1i—Zn1—O1—C6 | 4.6 (2) | O1—C6—C7—C8 | 13.0 (3) |
O2i—Zn1—N1—C1 | −44.3 (3) | O2—C6—C7—C8 | −168.9 (2) |
O1—Zn1—N1—C1 | 138.3 (2) | C12—C7—C8—C9 | 0.3 (3) |
O4ii—Zn1—N1—C1 | 47.8 (2) | C6—C7—C8—C9 | −175.3 (2) |
O5iii—Zn1—N1—C1 | −134.6 (2) | C7—C8—C9—C10 | 0.5 (3) |
Zn1i—Zn1—N1—C1 | 156.6 (2) | C13—O3—C10—C9 | −164.7 (2) |
O2i—Zn1—N1—C5 | 140.5 (2) | C13—O3—C10—C11 | 15.5 (3) |
O1—Zn1—N1—C5 | −36.8 (2) | C8—C9—C10—O3 | 179.4 (2) |
O4ii—Zn1—N1—C5 | −127.3 (2) | C8—C9—C10—C11 | −0.8 (3) |
O5iii—Zn1—N1—C5 | 50.3 (2) | O3—C10—C11—C12 | −179.9 (2) |
Zn1i—Zn1—N1—C5 | −18.6 (3) | C9—C10—C11—C12 | 0.3 (3) |
C5—N1—C1—C2 | 1.5 (5) | C8—C7—C12—C11 | −0.8 (3) |
Zn1—N1—C1—C2 | −173.7 (3) | C6—C7—C12—C11 | 174.9 (2) |
N1—C1—C2—C3 | 0.3 (7) | C10—C11—C12—C7 | 0.5 (3) |
C1—C2—C3—C4 | −1.6 (6) | C10—O3—C13—C14 | 62.2 (3) |
C2—C3—C4—C5 | 1.0 (5) | Zn1v—O5—C14—O4 | 10.9 (4) |
C1—N1—C5—C4 | −2.1 (4) | Zn1v—O5—C14—C13 | −170.1 (2) |
Zn1—N1—C5—C4 | 173.3 (2) | Zn1iv—O4—C14—O5 | −4.5 (3) |
C3—C4—C5—N1 | 0.8 (4) | Zn1iv—O4—C14—C13 | 176.5 (1) |
Zn1—O1—C6—O2 | −8.1 (4) | O3—C13—C14—O5 | 13.0 (3) |
Zn1—O1—C6—C7 | 169.9 (2) | O3—C13—C14—O4 | −167.9 (2) |
Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) −x+1, y+1/2, −z+3/2; (iii) x, −y+1/2, z−1/2; (iv) −x+1, y−1/2, −z+3/2; (v) x, −y+1/2, z+1/2. |