metal-organic compounds
The zinc atom in the title compound, {[Zn(C10H8O6)(C3H4N2)2]·4H2O}n, shows tetrahedral coordination; this atom, which lies on a position of site symmetry 2, is covalently bonded to the carboxyl O atom of one arm of the phenylenedioxydiacetate unit and datively bonded to the imidazole heterocycle. The polymeric chains propagate along the shortest axis of the orthorhombic unit cell and are assembled into layers. The phenylenedicarboxylate moiety lies on an inversion center and two of the three independent uncoordinated water molecules lie on twofold axes.
Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536804020744/ci6422sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536804020744/ci6422Isup2.hkl |
CCDC reference: 222950
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.
catena-Poly[[[bis(1H-imidazole-κN3)zinc(II)]-µ-1,4-
phenylenedioxydiacetatoκ2O:O'] tetrahydrate] top
Crystal data top
[Zn(C10H8O6)(C3H4N2)2]·4H2O | F(000) = 4128 |
Mr = 497.76 | Dx = 1.522 Mg m−3 |
Orthorhombic, Fddd | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -F 2uv 2vw | Cell parameters from 22377 reflections |
a = 11.323 (1) Å | θ = 3.2–27.3° |
b = 18.517 (2) Å | µ = 1.19 mm−1 |
c = 41.438 (4) Å | T = 295 K |
V = 8688 (1) Å3 | Prism, colorless |
Z = 16 | 0.39 × 0.27 × 0.18 mm |
Data collection top
Rigaku R-AXIS RAPID diffractometer | 2493 independent reflections |
Radiation source: fine-focus sealed tube | 2045 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.034 |
ω scans | θmax = 27.5°, θmin = 3.2° |
Absorption correction: multi-scan (ABSCOR; Higashi, 1995) | h = −14→14 |
Tmin = 0.608, Tmax = 0.814 | k = −24→23 |
19839 measured reflections | l = −53→53 |
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)] = 0.063 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.203 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.09 | w = 1/[σ2(Fo2) + (0.1307P)2 + 17.4198P] where P = (Fo2 + 2Fc2)/3 |
2493 reflections | (Δ/σ)max = 0.001 |
142 parameters | Δρmax = 0.98 e Å−3 |
20 restraints | Δρmin = −0.70 e Å−3 |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
x | y | z | Uiso*/Ueq | ||
Zn1 | 0.6250 | 0.6250 | 0.555143 (15) | 0.0517 (3) | |
O1 | 0.5028 (2) | 0.5935 (2) | 0.52412 (7) | 0.063 (1) | |
O2 | 0.3886 (3) | 0.5762 (2) | 0.56657 (8) | 0.076 (1) | |
O3 | 0.2052 (2) | 0.5387 (2) | 0.53193 (7) | 0.067 (1) | |
O1w | 0.9723 (8) | 0.4480 (5) | 0.6522 (2) | 0.212 (4) | |
O2w | 0.8750 | 0.3750 | 0.7146 (2) | 0.134 (3) | |
O3w | 0.1250 | 0.6250 | 0.5931 (3) | 0.39 (1) | |
N1 | 0.6805 (3) | 0.53752 (19) | 0.5785 (1) | 0.060 (1) | |
N2 | 0.7895 (5) | 0.4646 (3) | 0.6070 (1) | 0.084 (1) | |
C1 | 0.7721 (4) | 0.5311 (3) | 0.5986 (1) | 0.072 (1) | |
C2 | 0.7051 (6) | 0.4238 (3) | 0.5921 (1) | 0.088 (2) | |
C3 | 0.6374 (4) | 0.4685 (3) | 0.5747 (1) | 0.074 (1) | |
C4 | 0.4050 (3) | 0.5768 (2) | 0.5377 (1) | 0.056 (1) | |
C5 | 0.3079 (3) | 0.5569 (2) | 0.5141 (1) | 0.056 (1) | |
C6 | 0.1060 (3) | 0.5191 (2) | 0.5148 (1) | 0.052 (1) | |
C7 | 0.0971 (3) | 0.5199 (2) | 0.4813 (1) | 0.054 (1) | |
C8 | −0.0085 (3) | 0.5002 (2) | 0.4666 (1) | 0.056 (1) | |
H1w1 | 0.9623 | 0.4811 | 0.6666 | 0.254* | |
H1w2 | 0.9551 | 0.4081 | 0.6631 | 0.254* | |
H2w | 0.9182 | 0.3505 | 0.7278 | 0.160* | |
H3w | 0.1550 | 0.5928 | 0.5803 | 0.471* | |
H2n | 0.8442 | 0.4490 | 0.6196 | 0.101* | |
H1 | 0.8178 | 0.5697 | 0.6057 | 0.086* | |
H2 | 0.6962 | 0.3740 | 0.5938 | 0.106* | |
H3 | 0.5726 | 0.4552 | 0.5622 | 0.089* | |
H5a | 0.2915 | 0.5974 | 0.4999 | 0.067* | |
H5b | 0.3324 | 0.5163 | 0.5009 | 0.067* | |
H7 | 0.1616 | 0.5337 | 0.4688 | 0.065* | |
H8 | −0.0140 | 0.4998 | 0.4442 | 0.067* |
Atomic displacement parameters (Å2) top
U11 | U22 | U33 | U12 | U13 | U23 | |
Zn1 | 0.0302 (4) | 0.0604 (4) | 0.0645 (5) | −0.0046 (2) | 0.000 | 0.000 |
O1 | 0.030 (1) | 0.075 (2) | 0.085 (2) | −0.012 (1) | −0.003 (1) | −0.005 (2) |
O2 | 0.051 (2) | 0.101 (3) | 0.076 (2) | −0.024 (2) | −0.009 (2) | −0.002 (2) |
O3 | 0.032 (1) | 0.104 (2) | 0.065 (2) | −0.019 (1) | −0.005 (1) | −0.002 (2) |
O1w | 0.208 (7) | 0.250 (7) | 0.177 (5) | 0.127 (6) | −0.074 (5) | −0.072 (5) |
O2w | 0.165 (7) | 0.139 (6) | 0.097 (4) | 0.005 (4) | 0.000 | 0.000 |
O3w | 0.39 (2) | 0.41 (2) | 0.38 (2) | −0.01 (1) | 0.000 | 0.000 |
N1 | 0.045 (2) | 0.067 (2) | 0.069 (2) | 0.002 (2) | 0.006 (2) | 0.003 (2) |
N2 | 0.085 (3) | 0.091 (3) | 0.077 (3) | 0.027 (3) | 0.007 (2) | 0.019 (2) |
C1 | 0.065 (3) | 0.083 (3) | 0.067 (2) | 0.014 (2) | 0.000 (2) | 0.000 (2) |
C2 | 0.099 (5) | 0.074 (3) | 0.092 (4) | 0.014 (3) | 0.027 (3) | 0.024 (3) |
C3 | 0.060 (3) | 0.071 (3) | 0.091 (3) | −0.012 (2) | 0.019 (2) | 0.008 (3) |
C4 | 0.033 (2) | 0.060 (2) | 0.075 (2) | −0.009 (2) | −0.0069 (16) | −0.001 (2) |
C5 | 0.027 (2) | 0.067 (2) | 0.073 (2) | −0.008 (2) | −0.004 (2) | 0.000 (2) |
C6 | 0.025 (2) | 0.062 (2) | 0.069 (2) | −0.006 (1) | −0.003 (1) | −0.003 (2) |
C7 | 0.030 (2) | 0.071 (2) | 0.062 (2) | −0.008 (2) | 0.006 (1) | −0.001 (2) |
C8 | 0.035 (2) | 0.074 (2) | 0.060 (2) | −0.010 (2) | 0.001 (2) | −0.001 (2) |
Geometric parameters (Å, º) top
Zn1—O1 | 1.977 (3) | C6—C8ii | 1.393 (5) |
Zn1—O1i | 1.977 (3) | C7—C8 | 1.393 (5) |
Zn1—N1 | 1.989 (4) | C8—C6ii | 1.393 (5) |
Zn1—N1i | 1.989 (4) | O1w—H1w1 | 0.86 |
O1—C4 | 1.280 (5) | O1w—H1w2 | 0.89 |
O2—C4 | 1.209 (5) | O2w—H2w | 0.86 |
O3—C6 | 1.377 (4) | O3w—H3w | 0.87 |
O3—C5 | 1.419 (5) | N2—H2n | 0.86 |
N1—C1 | 1.335 (6) | C1—H1 | 0.93 |
N1—C3 | 1.378 (6) | C2—H2 | 0.93 |
N2—C1 | 1.294 (6) | C3—H3 | 0.93 |
N2—C2 | 1.366 (8) | C5—H5a | 0.97 |
C2—C3 | 1.339 (8) | C5—H5b | 0.97 |
C4—C5 | 1.518 (5) | C7—H7 | 0.93 |
C6—C7 | 1.392 (5) | C8—H8 | 0.93 |
O1—Zn1—O1i | 98.9 (2) | C7—C6—C8ii | 119.9 (3) |
O1—Zn1—N1 | 107.3 (1) | C6—C7—C8 | 119.8 (3) |
O1—Zn1—N1i | 109.6 (1) | C6ii—C8—C7 | 120.3 (4) |
O1i—Zn1—N1 | 109.6 (1) | H1w1—O1w—H1w2 | 102.1 |
O1i—Zn1—N1i | 107.3 (1) | C1—N2—H2n | 126.3 |
N1—Zn1—N1i | 121.7 (2) | C2—N2—H2n | 126.3 |
C4—O1—Zn1 | 113.0 (3) | N2—C1—H1 | 124.1 |
C6—O3—C5 | 117.6 (3) | N1—C1—H1 | 124.1 |
C1—N1—C3 | 105.3 (4) | C3—C2—H2 | 126.2 |
C1—N1—Zn1 | 128.4 (3) | N2—C2—H2 | 126.2 |
C3—N1—Zn1 | 126.0 (3) | C2—C3—H3 | 126.0 |
C1—N2—C2 | 107.3 (5) | N1—C3—H3 | 126.0 |
N2—C1—N1 | 111.8 (5) | O3—C5—H5a | 110.0 |
C3—C2—N2 | 107.6 (5) | C4—C5—H5a | 110.0 |
C2—C3—N1 | 108.0 (5) | O3—C5—H5b | 110.0 |
O2—C4—O1 | 124.8 (4) | C4—C5—H5b | 110.0 |
O2—C4—C5 | 121.6 (4) | H5a—C5—H5b | 108.4 |
O1—C4—C5 | 113.6 (4) | C6—C7—H7 | 120.1 |
O3—C5—C4 | 108.4 (3) | C8—C7—H7 | 120.1 |
O3—C6—C7 | 124.7 (3) | C6ii—C8—H8 | 119.9 |
O3—C6—C8ii | 115.4 (3) | C7—C8—H8 | 119.9 |
O1i—Zn1—O1—C4 | −173.0 (3) | N2—C2—C3—N1 | 0.6 (6) |
N1i—Zn1—O1—C4 | −60.9 (3) | C1—N1—C3—C2 | −0.8 (5) |
N1—Zn1—O1—C4 | 73.2 (3) | Zn1—N1—C3—C2 | 173.8 (3) |
O1—Zn1—N1—C1 | 170.7 (4) | Zn1—O1—C4—O2 | −3.7 (6) |
O1i—Zn1—N1—C1 | 64.2 (4) | Zn1—O1—C4—C5 | 176.4 (3) |
N1i—Zn1—N1—C1 | −62.0 (4) | C6—O3—C5—C4 | 179.9 (3) |
O1—Zn1—N1—C3 | −2.7 (4) | O2—C4—C5—O3 | −0.7 (6) |
O1i—Zn1—N1—C3 | −109.2 (4) | O1—C4—C5—O3 | 179.3 (3) |
N1i—Zn1—N1—C3 | 124.6 (4) | C5—O3—C6—C7 | −4.0 (6) |
C2—N2—C1—N1 | −0.5 (6) | C5—O3—C6—C8ii | 178.4 (4) |
C3—N1—C1—N2 | 0.8 (5) | O3—C6—C7—C8 | −178.9 (4) |
Zn1—N1—C1—N2 | −173.6 (3) | C8ii—C6—C7—C8 | −1.3 (7) |
C1—N2—C2—C3 | 0.0 (6) | C6—C7—C8—C6ii | 1.3 (7) |
Symmetry codes: (i) −x+5/4, −y+5/4, z; (ii) −x, −y+1, −z+1. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H2n···O1w | 0.86 | 1.98 | 2.808 (8) | 161 |
O1w—H1w1···O2iii | 0.86 | 2.21 | 2.980 (8) | 148 |
O1w—H1w2···O2w | 0.89 | 2.40 | 3.12 (1) | 139 |
O3w—H3w···O3 | 0.87 | 2.31 | 3.13 (1) | 158 |
O2w—H2w···O1iv | 0.86 | 2.12 | 2.889 (7) | 148 |
Symmetry codes: (iii) −x+5/4, y, −z+5/4; (iv) −x+3/2, y−1/4, z+1/4. |