Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807050611/bg2117sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807050611/bg2117Isup2.hkl |
CCDC reference: 667205
Key indicators
- Single-crystal X-ray study
- T = 295 K
- Mean (C-C) = 0.004 Å
- R factor = 0.039
- wR factor = 0.118
- Data-to-parameter ratio = 15.8
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for O1 PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for O2 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for Zn1 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C13 PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........ 3
Alert level G PLAT794_ALERT_5_G Check Predicted Bond Valency for Zn1 (2) 1.79 PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints ....... 6
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 5 ALERT level C = Check and explain 2 ALERT level G = General alerts; check 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 4 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
The title complex was prepared by the addition of zinc diacetate dihydrate (10 mmol), 4,4'-bipyridine (10 mmol) to a solution of 3-(p-CPOPH2) (15 mmol) in H2O/EtOH (V/V = 1:1), and the pH value was adjusted to 5 with a NaOH (0.2 M) solution. Colorless crystals were obtained from the filtered solution at room temperature over several days. CH&N analysis. Calc. for C30H32N2O13Zn: C 52.01, H 4.66, N 4.05%. Found: C 52.00, H 4.68, N 4.04%.
H atoms attached to carbon were placed at calculated positions with C—H = 0.93 or 0.97Å and Uiso(H) = 1.2Ueq (C) and were included in the refinement in the riding model approximation. Those bound to oxygen were located in difference Fourier maps and refined with the O—H distance restrained to 0.85 (1)Å and Uiso(H) = 1.5Ueq(O).
Our studies have addressed the metal derivatives of carboxyphenoxypropionic acids which are regarded as excellent candidates for the construction of supramolecular architectures. In this line 3-(p-CPOPH2) is not only a multiple coordination ligand, but also may form regular hydrogen bonds by functioning both as a hydrogen bond donor and acceptor(Gao & Ng, 2006). We have recently reported the structures of the cobalt(II) and the copper(II) complexes incorporating the 3-(4-carboxylatophenoxy)propionate group (Kong et al., 2007; Xiao et al., 2007).
The molecular structure of the title complex [Zn(C10H8N2)(C10H9O5)2(H2O)]n.2n(H2O)is shown in Fig. 1. The 3-(p-CPOP)2- ligand coordinates in a chelating fashion to the Zn atom through the deprotonated carboxylate group while the remaining protonated carboxyl group forms a hydrogen bond with an uncoordinated water molecule. The Zn atom, which lies on a two fold axis displays a distorted pentagonal bipyramid geometry involving four O atoms of the two 3-(4-carboxylatophenoxy)propionic acid groups, two N atom from two 4,4'-bipyridine ligands and one water molecule also lying on the two fold axis. The 4,4'-bipyridine ligands act in a bis-monodentate bridging mode to link two Zn atoms, giving rise to a one-dimensional chain running along the c axis. Furthermore, a three-dimensional supramolecular network is constructed via π-π stacking interactions between the adjacent 3-(p-CPOP)2- ligand rings (centroid-centroid distance being 3.910 Å) and hydrogen-bonding interactions (Fig 2, Table 2).
3-(4-Carboxyphenoxy)propionic acid [3-(p-CPOPH2)] has been reported previously (Gao & Ng, 2006). In our previous work, the copper(II) and cobalt(II) complexes of 3-(p-CPOPH2) have been characterized by X-ray crystallography (Xiao et al., 2007; Kong et al., 2007).
Data collection: RAPID-AUTO (Rigaku Corporation, 1998); cell refinement: RAPID-AUTO (Rigaku Corporation, 1998); 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 (Sheldrick, 1997).
[Zn(C10H9O5)2(C10H8N2)(H2O)]·2H2O | F(000) = 720 |
Mr = 693.95 | Dx = 1.510 Mg m−3 |
Monoclinic, P2/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2yc | Cell parameters from 9291 reflections |
a = 11.109 (2) Å | θ = 3.4–27.5° |
b = 6.0063 (12) Å | µ = 0.88 mm−1 |
c = 22.871 (5) Å | T = 295 K |
β = 90.54 (3)° | Block, colorless |
V = 1525.9 (5) Å3 | 0.28 × 0.24 × 0.18 mm |
Z = 2 |
Rigaku R-AXIS RAPID diffractometer | 3498 independent reflections |
Radiation source: fine-focus sealed tube | 2191 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.052 |
Detector resolution: 10.000 pixels mm-1 | θmax = 27.5°, θmin = 3.4° |
ω scans | h = −14→14 |
Absorption correction: multi-scan (ABSCOR; Higashi, 1995) | k = −7→7 |
Tmin = 0.791, Tmax = 0.858 | l = −29→28 |
14159 measured reflections |
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)] = 0.039 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.118 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.12 | w = 1/[σ2(Fo2) + (0.0497P)2 + 0.3569P] where P = (Fo2 + 2Fc2)/3 |
3498 reflections | (Δ/σ)max < 0.001 |
221 parameters | Δρmax = 0.78 e Å−3 |
6 restraints | Δρmin = −0.74 e Å−3 |
[Zn(C10H9O5)2(C10H8N2)(H2O)]·2H2O | V = 1525.9 (5) Å3 |
Mr = 693.95 | Z = 2 |
Monoclinic, P2/c | Mo Kα radiation |
a = 11.109 (2) Å | µ = 0.88 mm−1 |
b = 6.0063 (12) Å | T = 295 K |
c = 22.871 (5) Å | 0.28 × 0.24 × 0.18 mm |
β = 90.54 (3)° |
Rigaku R-AXIS RAPID diffractometer | 3498 independent reflections |
Absorption correction: multi-scan (ABSCOR; Higashi, 1995) | 2191 reflections with I > 2σ(I) |
Tmin = 0.791, Tmax = 0.858 | Rint = 0.052 |
14159 measured reflections |
R[F2 > 2σ(F2)] = 0.039 | 6 restraints |
wR(F2) = 0.118 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.12 | Δρmax = 0.78 e Å−3 |
3498 reflections | Δρmin = −0.74 e Å−3 |
221 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 | ||
Zn1 | 0.5000 | 0.44267 (8) | 0.7500 | 0.03760 (17) | |
O1W | 0.5000 | 0.1010 (5) | 0.7500 | 0.0547 (8) | |
O1 | 0.2947 (2) | 0.3990 (4) | 0.74492 (10) | 0.0635 (7) | |
O2 | 0.3670 (2) | 0.7310 (4) | 0.73806 (10) | 0.0644 (7) | |
O2W | 0.1267 (3) | 1.7261 (4) | 0.32819 (10) | 0.0668 (7) | |
O3 | 0.1899 (2) | 0.7907 (4) | 0.62824 (9) | 0.0560 (6) | |
O4 | 0.1688 (2) | 1.1631 (4) | 0.36930 (9) | 0.0604 (6) | |
O5 | 0.1102 (3) | 1.4599 (4) | 0.41913 (9) | 0.0631 (7) | |
N1 | 0.5053 (2) | 0.4529 (4) | 0.65511 (9) | 0.0400 (5) | |
C1 | 0.2792 (3) | 0.6033 (6) | 0.73615 (11) | 0.0454 (7) | |
C2 | 0.1545 (3) | 0.6905 (5) | 0.72592 (13) | 0.0445 (7) | |
H1 | 0.1222 | 0.7403 | 0.7629 | 0.053* | |
H2 | 0.1040 | 0.5698 | 0.7118 | 0.053* | |
C3 | 0.1476 (3) | 0.8794 (6) | 0.68294 (12) | 0.0525 (8) | |
H4 | 0.0654 | 0.9321 | 0.6789 | 0.063* | |
H3 | 0.1980 | 1.0023 | 0.6957 | 0.063* | |
C4 | 0.1775 (3) | 0.9169 (5) | 0.57937 (12) | 0.0431 (7) | |
C5 | 0.1268 (3) | 1.1283 (5) | 0.57735 (13) | 0.0461 (7) | |
H5 | 0.1000 | 1.1966 | 0.6113 | 0.055* | |
C6 | 0.1166 (3) | 1.2357 (5) | 0.52392 (13) | 0.0455 (7) | |
H6 | 0.0826 | 1.3771 | 0.5224 | 0.055* | |
C7 | 0.1560 (3) | 1.1377 (5) | 0.47271 (12) | 0.0389 (6) | |
C8 | 0.2079 (3) | 0.9277 (5) | 0.47588 (12) | 0.0440 (7) | |
H8 | 0.2356 | 0.8604 | 0.4420 | 0.053* | |
C9 | 0.2191 (3) | 0.8180 (5) | 0.52833 (12) | 0.0444 (7) | |
H9 | 0.2544 | 0.6777 | 0.5298 | 0.053* | |
C10 | 0.1456 (3) | 1.2510 (5) | 0.41552 (13) | 0.0444 (7) | |
C11 | 0.4569 (4) | 0.2967 (6) | 0.62145 (13) | 0.0592 (9) | |
H11 | 0.4239 | 0.1722 | 0.6394 | 0.071* | |
C12 | 0.4531 (3) | 0.3088 (6) | 0.56117 (13) | 0.0573 (9) | |
H12 | 0.4175 | 0.1945 | 0.5397 | 0.069* | |
C13 | 0.5017 (2) | 0.4896 (5) | 0.53254 (11) | 0.0380 (6) | |
C14 | 0.5498 (3) | 0.6531 (6) | 0.56790 (13) | 0.0560 (9) | |
H14 | 0.5819 | 0.7809 | 0.5512 | 0.067* | |
C15 | 0.5506 (3) | 0.6288 (6) | 0.62788 (13) | 0.0577 (9) | |
H15 | 0.5847 | 0.7417 | 0.6504 | 0.069* | |
H1W1 | 0.4378 (6) | 0.021 (3) | 0.7461 (18) | 0.087* | |
H2W2 | 0.178 (3) | 1.692 (5) | 0.3021 (14) | 0.087* | |
H2W1 | 0.145 (3) | 1.854 (4) | 0.3420 (15) | 0.087* | |
H10 | 0.119 (4) | 1.523 (6) | 0.3861 (9) | 0.087* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Zn1 | 0.0430 (3) | 0.0433 (3) | 0.0264 (2) | 0.000 | −0.00367 (18) | 0.000 |
O1W | 0.0471 (18) | 0.0484 (18) | 0.069 (2) | 0.000 | −0.0052 (17) | 0.000 |
O1 | 0.0719 (17) | 0.0668 (16) | 0.0520 (13) | 0.0202 (13) | 0.0076 (12) | 0.0169 (12) |
O2 | 0.0479 (14) | 0.0886 (18) | 0.0567 (14) | −0.0157 (13) | −0.0051 (12) | −0.0120 (12) |
O2W | 0.107 (2) | 0.0466 (13) | 0.0470 (14) | 0.0085 (14) | 0.0125 (14) | −0.0026 (11) |
O3 | 0.0745 (16) | 0.0593 (13) | 0.0341 (11) | 0.0200 (12) | 0.0034 (11) | 0.0097 (10) |
O4 | 0.100 (2) | 0.0482 (12) | 0.0331 (11) | 0.0059 (13) | 0.0030 (12) | −0.0029 (10) |
O5 | 0.108 (2) | 0.0446 (13) | 0.0374 (11) | 0.0164 (13) | 0.0074 (13) | 0.0050 (10) |
N1 | 0.0436 (14) | 0.0492 (14) | 0.0272 (11) | −0.0028 (12) | −0.0038 (10) | −0.0012 (11) |
C1 | 0.0460 (18) | 0.068 (2) | 0.0223 (13) | −0.0034 (16) | −0.0011 (12) | 0.0004 (13) |
C2 | 0.0369 (16) | 0.0593 (18) | 0.0372 (15) | 0.0018 (14) | −0.0029 (13) | 0.0077 (14) |
C3 | 0.060 (2) | 0.062 (2) | 0.0360 (15) | 0.0146 (17) | 0.0026 (15) | 0.0030 (14) |
C4 | 0.0448 (17) | 0.0488 (17) | 0.0356 (14) | 0.0033 (14) | −0.0041 (12) | 0.0058 (13) |
C5 | 0.0548 (19) | 0.0484 (17) | 0.0353 (15) | 0.0104 (15) | 0.0031 (14) | −0.0007 (13) |
C6 | 0.0528 (19) | 0.0436 (16) | 0.0402 (16) | 0.0070 (14) | −0.0010 (14) | 0.0006 (13) |
C7 | 0.0431 (17) | 0.0396 (15) | 0.0340 (14) | −0.0010 (13) | −0.0036 (12) | 0.0000 (12) |
C8 | 0.0525 (18) | 0.0436 (16) | 0.0358 (14) | 0.0018 (14) | −0.0009 (13) | −0.0045 (13) |
C9 | 0.0485 (18) | 0.0421 (16) | 0.0426 (16) | 0.0078 (14) | −0.0046 (14) | 0.0008 (14) |
C10 | 0.0548 (19) | 0.0389 (16) | 0.0396 (16) | −0.0011 (14) | −0.0036 (14) | −0.0023 (13) |
C11 | 0.088 (3) | 0.056 (2) | 0.0339 (16) | −0.0196 (19) | −0.0054 (17) | 0.0003 (15) |
C12 | 0.087 (3) | 0.0542 (19) | 0.0307 (15) | −0.0229 (18) | −0.0090 (16) | −0.0016 (14) |
C13 | 0.0366 (15) | 0.0492 (16) | 0.0283 (13) | 0.0007 (12) | −0.0026 (12) | −0.0028 (12) |
C14 | 0.073 (2) | 0.063 (2) | 0.0324 (15) | −0.0270 (18) | −0.0031 (15) | 0.0010 (15) |
C15 | 0.075 (2) | 0.067 (2) | 0.0309 (15) | −0.0289 (19) | −0.0075 (15) | −0.0049 (15) |
Zn1—O1W | 2.052 (3) | C3—H4 | 0.9700 |
Zn1—N1 | 2.172 (2) | C3—H3 | 0.9700 |
Zn1—O2 | 2.291 (3) | C4—C5 | 1.390 (4) |
Zn1—O1 | 2.298 (3) | C4—C9 | 1.392 (4) |
Zn1—O1i | 2.298 (3) | C5—C6 | 1.385 (4) |
Zn1—N1i | 2.172 (2) | C5—H5 | 0.9300 |
Zn1—O2i | 2.291 (3) | C6—C7 | 1.385 (4) |
O1W—H1W1 | 0.846 (10) | C6—H6 | 0.9300 |
O1—C1 | 1.255 (4) | C7—C8 | 1.388 (4) |
O2—C1 | 1.241 (4) | C7—C10 | 1.478 (4) |
O2W—H2W2 | 0.85 (3) | C8—C9 | 1.373 (4) |
O2W—H2W1 | 0.85 (3) | C8—H8 | 0.9300 |
O3—C4 | 1.357 (3) | C9—H9 | 0.9300 |
O3—C3 | 1.442 (3) | C11—C12 | 1.381 (4) |
O4—C10 | 1.212 (3) | C11—H11 | 0.9300 |
O5—C10 | 1.317 (4) | C12—C13 | 1.381 (4) |
O5—H10 | 0.85 (3) | C12—H12 | 0.9300 |
N1—C11 | 1.324 (4) | C13—C14 | 1.376 (4) |
N1—C15 | 1.328 (4) | C13—C13ii | 1.494 (5) |
C1—C2 | 1.497 (4) | C14—C15 | 1.379 (4) |
C2—C3 | 1.503 (4) | C14—H14 | 0.9300 |
C2—H1 | 0.9700 | C15—H15 | 0.9300 |
C2—H2 | 0.9700 | ||
O1W—Zn1—N1 | 91.62 (7) | C2—C3—H4 | 110.6 |
O1W—Zn1—N1i | 91.62 (7) | O3—C3—H3 | 110.6 |
N1—Zn1—N1i | 176.76 (13) | C2—C3—H3 | 110.6 |
O1W—Zn1—O2i | 139.10 (6) | H4—C3—H3 | 108.7 |
N1—Zn1—O2i | 94.27 (9) | O3—C4—C5 | 125.2 (3) |
N1i—Zn1—O2i | 83.28 (9) | O3—C4—C9 | 114.9 (3) |
O1W—Zn1—O2 | 139.10 (6) | C5—C4—C9 | 120.0 (3) |
N1—Zn1—O2 | 83.28 (9) | C6—C5—C4 | 119.0 (3) |
N1i—Zn1—O2 | 94.27 (9) | C6—C5—H5 | 120.5 |
O2i—Zn1—O2 | 81.80 (12) | C4—C5—H5 | 120.5 |
O1W—Zn1—O1 | 83.44 (6) | C7—C6—C5 | 121.6 (3) |
N1—Zn1—O1 | 89.35 (9) | C7—C6—H6 | 119.2 |
N1i—Zn1—O1 | 91.02 (9) | C5—C6—H6 | 119.2 |
O2i—Zn1—O1 | 136.98 (9) | C6—C7—C8 | 118.4 (3) |
O2—Zn1—O1 | 56.05 (8) | C6—C7—C10 | 122.0 (3) |
O1W—Zn1—O1i | 83.44 (6) | C8—C7—C10 | 119.6 (2) |
N1—Zn1—O1i | 91.02 (9) | C9—C8—C7 | 121.0 (3) |
N1i—Zn1—O1i | 89.35 (9) | C9—C8—H8 | 119.5 |
O2i—Zn1—O1i | 56.05 (8) | C7—C8—H8 | 119.5 |
O2—Zn1—O1i | 136.98 (9) | C8—C9—C4 | 120.0 (3) |
O1—Zn1—O1i | 166.88 (12) | C8—C9—H9 | 120.0 |
Zn1—O1W—H1W1 | 124.6 (11) | C4—C9—H9 | 120.0 |
C1—O1—Zn1 | 91.8 (2) | O4—C10—O5 | 122.4 (3) |
C1—O2—Zn1 | 92.5 (2) | O4—C10—C7 | 123.8 (3) |
H2W2—O2W—H2W1 | 108.5 (16) | O5—C10—C7 | 113.8 (2) |
C4—O3—C3 | 118.5 (2) | N1—C11—C12 | 123.5 (3) |
C10—O5—H10 | 109 (3) | N1—C11—H11 | 118.2 |
C11—N1—C15 | 116.4 (2) | C12—C11—H11 | 118.2 |
C11—N1—Zn1 | 123.1 (2) | C11—C12—C13 | 120.4 (3) |
C15—N1—Zn1 | 120.32 (19) | C11—C12—H12 | 119.8 |
O2—C1—O1 | 119.4 (3) | C13—C12—H12 | 119.8 |
O2—C1—C2 | 121.0 (3) | C14—C13—C12 | 115.7 (3) |
O1—C1—C2 | 119.5 (3) | C14—C13—C13ii | 122.2 (3) |
C1—C2—C3 | 114.1 (3) | C12—C13—C13ii | 122.1 (3) |
C1—C2—H1 | 108.7 | C13—C14—C15 | 120.5 (3) |
C3—C2—H1 | 108.7 | C13—C14—H14 | 119.7 |
C1—C2—H2 | 108.7 | C15—C14—H14 | 119.7 |
C3—C2—H2 | 108.7 | N1—C15—C14 | 123.5 (3) |
H1—C2—H2 | 107.6 | N1—C15—H15 | 118.3 |
O3—C3—C2 | 105.9 (2) | C14—C15—H15 | 118.3 |
O3—C3—H4 | 110.6 | ||
O1W—Zn1—O1—C1 | −171.21 (17) | C4—O3—C3—C2 | 170.9 (3) |
N1—Zn1—O1—C1 | −79.51 (17) | C1—C2—C3—O3 | 61.9 (3) |
N1i—Zn1—O1—C1 | 97.28 (17) | C3—O3—C4—C5 | 0.0 (5) |
O2i—Zn1—O1—C1 | 16.1 (2) | C3—O3—C4—C9 | −179.2 (3) |
O2—Zn1—O1—C1 | 2.82 (16) | O3—C4—C5—C6 | −178.1 (3) |
O1i—Zn1—O1—C1 | −171.21 (17) | C9—C4—C5—C6 | 1.1 (5) |
O1W—Zn1—O2—C1 | 6.2 (2) | C4—C5—C6—C7 | −0.1 (5) |
N1—Zn1—O2—C1 | 90.92 (18) | C5—C6—C7—C8 | −0.8 (5) |
N1i—Zn1—O2—C1 | −91.20 (18) | C5—C6—C7—C10 | −180.0 (3) |
O2i—Zn1—O2—C1 | −173.8 (2) | C6—C7—C8—C9 | 0.7 (5) |
O1—Zn1—O2—C1 | −2.85 (16) | C10—C7—C8—C9 | 179.9 (3) |
O1i—Zn1—O2—C1 | 175.17 (15) | C7—C8—C9—C4 | 0.3 (5) |
O1W—Zn1—N1—C11 | 30.2 (3) | O3—C4—C9—C8 | 178.1 (3) |
O2i—Zn1—N1—C11 | 169.7 (3) | C5—C4—C9—C8 | −1.2 (5) |
O2—Zn1—N1—C11 | −109.1 (3) | C6—C7—C10—O4 | −173.1 (3) |
O1—Zn1—N1—C11 | −53.3 (3) | C8—C7—C10—O4 | 7.8 (5) |
O1i—Zn1—N1—C11 | 113.6 (3) | C6—C7—C10—O5 | 8.0 (4) |
O1W—Zn1—N1—C15 | −154.9 (3) | C8—C7—C10—O5 | −171.2 (3) |
O2i—Zn1—N1—C15 | −15.4 (3) | C15—N1—C11—C12 | 0.6 (5) |
O2—Zn1—N1—C15 | 65.8 (3) | Zn1—N1—C11—C12 | 175.7 (3) |
O1—Zn1—N1—C15 | 121.7 (3) | N1—C11—C12—C13 | 0.4 (6) |
O1i—Zn1—N1—C15 | −71.4 (3) | C11—C12—C13—C14 | −1.6 (5) |
Zn1—O2—C1—O1 | 5.0 (3) | C11—C12—C13—C13ii | −179.3 (4) |
Zn1—O2—C1—C2 | −177.5 (2) | C12—C13—C14—C15 | 1.7 (5) |
Zn1—O1—C1—O2 | −5.0 (3) | C13ii—C13—C14—C15 | 179.5 (4) |
Zn1—O1—C1—C2 | 177.5 (2) | C11—N1—C15—C14 | −0.4 (5) |
O2—C1—C2—C3 | 37.8 (4) | Zn1—N1—C15—C14 | −175.7 (3) |
O1—C1—C2—C3 | −144.6 (3) | C13—C14—C15—N1 | −0.8 (6) |
Symmetry codes: (i) −x+1, y, −z+3/2; (ii) −x+1, −y+1, −z+1. |
D—H···A | D—H | H···A | D···A | D—H···A |
O1W—H1W1···O2iii | 0.85 (1) | 1.92 (2) | 2.681 (4) | 149 (1) |
O2W—H2W2···O1iv | 0.85 (3) | 1.93 (3) | 2.782 (3) | 177 (4) |
O2W—H2W1···O4v | 0.85 (3) | 1.98 (3) | 2.826 (3) | 173 (4) |
O5—H10···O2W | 0.85 (3) | 1.80 (2) | 2.632 (3) | 164 (4) |
Symmetry codes: (iii) x, y−1, z; (iv) x, −y+2, z−1/2; (v) x, y+1, z. |
Experimental details
Crystal data | |
Chemical formula | [Zn(C10H9O5)2(C10H8N2)(H2O)]·2H2O |
Mr | 693.95 |
Crystal system, space group | Monoclinic, P2/c |
Temperature (K) | 295 |
a, b, c (Å) | 11.109 (2), 6.0063 (12), 22.871 (5) |
β (°) | 90.54 (3) |
V (Å3) | 1525.9 (5) |
Z | 2 |
Radiation type | Mo Kα |
µ (mm−1) | 0.88 |
Crystal size (mm) | 0.28 × 0.24 × 0.18 |
Data collection | |
Diffractometer | Rigaku R-AXIS RAPID |
Absorption correction | Multi-scan (ABSCOR; Higashi, 1995) |
Tmin, Tmax | 0.791, 0.858 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 14159, 3498, 2191 |
Rint | 0.052 |
(sin θ/λ)max (Å−1) | 0.649 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.039, 0.118, 1.12 |
No. of reflections | 3498 |
No. of parameters | 221 |
No. of restraints | 6 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.78, −0.74 |
Computer programs: RAPID-AUTO (Rigaku Corporation, 1998), CrystalStructure (Rigaku/MSC, 2002), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), ORTEPII (Johnson, 1976).
D—H···A | D—H | H···A | D···A | D—H···A |
O1W—H1W1···O2i | 0.846 (10) | 1.919 (16) | 2.681 (4) | 149.3 (14) |
O2W—H2W2···O1ii | 0.85 (3) | 1.93 (3) | 2.782 (3) | 177 (4) |
O2W—H2W1···O4iii | 0.85 (3) | 1.98 (3) | 2.826 (3) | 173 (4) |
O5—H10···O2W | 0.85 (3) | 1.803 (15) | 2.632 (3) | 164 (4) |
Symmetry codes: (i) x, y−1, z; (ii) x, −y+2, z−1/2; (iii) x, y+1, z. |
Our studies have addressed the metal derivatives of carboxyphenoxypropionic acids which are regarded as excellent candidates for the construction of supramolecular architectures. In this line 3-(p-CPOPH2) is not only a multiple coordination ligand, but also may form regular hydrogen bonds by functioning both as a hydrogen bond donor and acceptor(Gao & Ng, 2006). We have recently reported the structures of the cobalt(II) and the copper(II) complexes incorporating the 3-(4-carboxylatophenoxy)propionate group (Kong et al., 2007; Xiao et al., 2007).
The molecular structure of the title complex [Zn(C10H8N2)(C10H9O5)2(H2O)]n.2n(H2O)is shown in Fig. 1. The 3-(p-CPOP)2- ligand coordinates in a chelating fashion to the Zn atom through the deprotonated carboxylate group while the remaining protonated carboxyl group forms a hydrogen bond with an uncoordinated water molecule. The Zn atom, which lies on a two fold axis displays a distorted pentagonal bipyramid geometry involving four O atoms of the two 3-(4-carboxylatophenoxy)propionic acid groups, two N atom from two 4,4'-bipyridine ligands and one water molecule also lying on the two fold axis. The 4,4'-bipyridine ligands act in a bis-monodentate bridging mode to link two Zn atoms, giving rise to a one-dimensional chain running along the c axis. Furthermore, a three-dimensional supramolecular network is constructed via π-π stacking interactions between the adjacent 3-(p-CPOP)2- ligand rings (centroid-centroid distance being 3.910 Å) and hydrogen-bonding interactions (Fig 2, Table 2).