Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807051318/bx2110sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807051318/bx2110Isup2.hkl |
CCDC reference: 667211
Key indicators
- Single-crystal X-ray study
- T = 295 K
- Mean (C-C) = 0.004 Å
- R factor = 0.032
- wR factor = 0.101
- Data-to-parameter ratio = 15.9
checkCIF/PLATON results
No syntax errors found
Alert level C CELLV02_ALERT_1_C The supplied cell volume s.u. differs from that calculated from the cell parameter s.u.'s by > 2 Calculated cell volume su = 6.28 Cell volume su given = 4.00 PLAT152_ALERT_1_C Supplied and Calc Volume s.u. Inconsistent ..... ? PLAT154_ALERT_1_C The su's on the Cell Angles are Equal (x 10000) 3000 Deg. PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 2.57 Ratio PLAT230_ALERT_2_C Hirshfeld Test Diff for O2 - C1 .. 5.50 su PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X) Zn1 - O2W .. 7.73 su PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........ 6
Alert level G PLAT794_ALERT_5_G Check Predicted Bond Valency for Zn1 (2) 1.98 PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints ....... 9
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 7 ALERT level C = Check and explain 2 ALERT level G = General alerts; check 3 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 3 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), 1,10-phenanthroline (10 mmol) to a solution of 3-(p-CPOPH2) (15 mmol) in H2O/MeOH (V/V = 1:1) solution, and the pH value was adjusted to 5 with NaOH (0.2 M) solution. Colorless crystals were obtained from the filtered solution at room temperature over several days. CH&N analysis. Calc. for C22H22N2O8Zn: C 52.04, H 4.37, N 5.52%. Found: C 52.05, H 4.38, N 5.50%.
The H atoms were placed in 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. The H atoms of hydroxyl groups 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. Thus, 3-(p-CPOPH2) may be not only multiple coordination possibilities, but also form regular hydrogen bonds by functioning as both a hydrogen bond donor and acceptor (Gao & Ng, 2006). Recently, we have reported the structures of cobalt(II) complex incorporating 3-(4-carboxylatophenoxy)propionate group, namely [Co(C10H9O5)2(C10H10O5)2(py)2], (Kong et al., 2007).
The molecular structure of the title complex is shown in Fig. 1. The 3-(p-CPOP)2- ligand coordinates in a monodentate fashion to the Zn atom through the carboxylate group. The Zn atom displays a distorted octahedral geometry involving one O atom of the 3-(4-carboxylatophenoxy)propionate group, two N atoms of 1,10-phenanthroline ligand and three water molecules. Furthermore, a three-dimensional supramolecular network is constructed via π-π stacking interactions between the 1,10-phenanthroline rings (centroid-centroid distance being 3.656 Å) and hydrogen-bonding interactions (Table 2).
The structure of 3-(4-carboxylatophenoxy)propionic acid [3-(p-CPOPH2)] has been reported previously (Gao & Ng, 2006). In a previous study, the cobalt(II) complex of 3-(p-CPOPH2) was characterized by X-ray crystallography (Kong et al., 2007).
Data collection: RAPID-AUTO (Rigaku, 1998); cell refinement: RAPID-AUTO (Rigaku, 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).
Fig. 1. Molecular structure of the title compound with 30% probability ellipsoid for the non-H atoms. Dashed lines indicate O—H···O hydrogen bonds. |
[Zn(C10H8O5)(C12H8N2)(H2O)3] | Z = 2 |
Mr = 507.79 | F(000) = 524 |
Triclinic, P1 | Dx = 1.524 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 7.7101 (15) Å | Cell parameters from 9001 reflections |
b = 12.987 (3) Å | θ = 3.1–27.5° |
c = 13.059 (3) Å | µ = 1.16 mm−1 |
α = 113.31 (3)° | T = 295 K |
β = 103.62 (3)° | Block, colorless |
γ = 100.99 (3)° | 0.34 × 0.24 × 0.20 mm |
V = 1106.4 (4) Å3 |
Rigaku R-AXIS RAPID diffractometer | 5015 independent reflections |
Radiation source: fine-focus sealed tube | 4188 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.022 |
Detector resolution: 10.000 pixels mm-1 | θmax = 27.5°, θmin = 3.1° |
ω scans | h = −10→9 |
Absorption correction: multi-scan (ABSCOR; Higashi, 1995) | k = −16→16 |
Tmin = 0.694, Tmax = 0.801 | l = −16→16 |
10928 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)] = 0.032 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.101 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.16 | w = 1/[σ2(Fo2) + (0.041P)2 + 0.6471P] where P = (Fo2 + 2Fc2)/3 |
5015 reflections | (Δ/σ)max < 0.001 |
316 parameters | Δρmax = 0.39 e Å−3 |
9 restraints | Δρmin = −0.33 e Å−3 |
[Zn(C10H8O5)(C12H8N2)(H2O)3] | γ = 100.99 (3)° |
Mr = 507.79 | V = 1106.4 (4) Å3 |
Triclinic, P1 | Z = 2 |
a = 7.7101 (15) Å | Mo Kα radiation |
b = 12.987 (3) Å | µ = 1.16 mm−1 |
c = 13.059 (3) Å | T = 295 K |
α = 113.31 (3)° | 0.34 × 0.24 × 0.20 mm |
β = 103.62 (3)° |
Rigaku R-AXIS RAPID diffractometer | 5015 independent reflections |
Absorption correction: multi-scan (ABSCOR; Higashi, 1995) | 4188 reflections with I > 2σ(I) |
Tmin = 0.694, Tmax = 0.801 | Rint = 0.022 |
10928 measured reflections |
R[F2 > 2σ(F2)] = 0.032 | 9 restraints |
wR(F2) = 0.101 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.16 | Δρmax = 0.39 e Å−3 |
5015 reflections | Δρmin = −0.33 e Å−3 |
316 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 | 0.45725 (4) | 0.57914 (2) | 0.84281 (2) | 0.03132 (10) | |
O1 | 0.5645 (2) | 0.44139 (14) | 0.82196 (16) | 0.0356 (4) | |
O1W | 0.5203 (3) | 0.64632 (17) | 1.02239 (16) | 0.0399 (4) | |
H1W1 | 0.633 (2) | 0.684 (2) | 1.070 (2) | 0.060* | |
H1W2 | 0.466 (3) | 0.600 (2) | 1.044 (3) | 0.060* | |
O2W | 0.1961 (2) | 0.46005 (17) | 0.8234 (2) | 0.0456 (5) | |
H2W1 | 0.098 (3) | 0.478 (3) | 0.832 (3) | 0.068* | |
H2W2 | 0.187 (4) | 0.3925 (16) | 0.819 (3) | 0.068* | |
O3W | 0.7211 (3) | 0.68984 (15) | 0.86547 (16) | 0.0385 (4) | |
H3W1 | 0.782 (4) | 0.7501 (16) | 0.9330 (16) | 0.058* | |
H3W2 | 0.777 (4) | 0.6381 (18) | 0.857 (2) | 0.058* | |
O2 | 0.8616 (2) | 0.50571 (15) | 0.83328 (17) | 0.0398 (4) | |
O3 | 0.5297 (2) | 0.20884 (15) | 0.59373 (16) | 0.0397 (4) | |
O4 | −0.0807 (3) | −0.13327 (18) | 0.08476 (18) | 0.0570 (5) | |
O5 | −0.1526 (3) | −0.23347 (16) | 0.18182 (19) | 0.0509 (5) | |
N1 | 0.3454 (3) | 0.52921 (18) | 0.65624 (18) | 0.0345 (4) | |
N2 | 0.3334 (3) | 0.71451 (19) | 0.84272 (19) | 0.0385 (5) | |
C1 | 0.7219 (3) | 0.4274 (2) | 0.81742 (19) | 0.0295 (5) | |
C2 | 0.7365 (3) | 0.3056 (2) | 0.7931 (2) | 0.0355 (5) | |
H1 | 0.8385 | 0.2951 | 0.7626 | 0.043* | |
H2 | 0.7678 | 0.3012 | 0.8673 | 0.043* | |
C3 | 0.5579 (3) | 0.2060 (2) | 0.7053 (2) | 0.0355 (5) | |
H3 | 0.5705 | 0.1307 | 0.6976 | 0.043* | |
H4 | 0.4521 | 0.2173 | 0.7314 | 0.043* | |
C4 | 0.3857 (3) | 0.1200 (2) | 0.4968 (2) | 0.0344 (5) | |
C5 | 0.3654 (4) | 0.1241 (2) | 0.3900 (2) | 0.0402 (6) | |
H5 | 0.4480 | 0.1852 | 0.3882 | 0.048* | |
C6 | 0.2245 (4) | 0.0390 (2) | 0.2872 (2) | 0.0401 (6) | |
H7 | 0.2126 | 0.0431 | 0.2165 | 0.048* | |
C7 | 0.0988 (3) | −0.0537 (2) | 0.2878 (2) | 0.0351 (5) | |
C8 | 0.1205 (4) | −0.0569 (2) | 0.3944 (2) | 0.0387 (6) | |
H8 | 0.0388 | −0.1184 | 0.3962 | 0.046* | |
C9 | 0.2617 (4) | 0.0295 (2) | 0.4990 (2) | 0.0402 (6) | |
H9 | 0.2726 | 0.0264 | 0.5701 | 0.048* | |
C10 | −0.0562 (4) | −0.1477 (2) | 0.1751 (2) | 0.0398 (6) | |
C11 | 0.3223 (5) | 0.8017 (3) | 0.9337 (3) | 0.0589 (8) | |
H11 | 0.3635 | 0.8051 | 1.0082 | 0.071* | |
C12 | 0.2510 (6) | 0.8896 (3) | 0.9231 (4) | 0.0763 (11) | |
H12 | 0.2439 | 0.9495 | 0.9895 | 0.092* | |
C13 | 0.1922 (5) | 0.8871 (3) | 0.8158 (4) | 0.0677 (10) | |
H13 | 0.1487 | 0.9468 | 0.8085 | 0.081* | |
C14 | 0.1975 (4) | 0.7939 (3) | 0.7155 (3) | 0.0494 (7) | |
C15 | 0.1320 (4) | 0.7806 (3) | 0.5974 (3) | 0.0577 (9) | |
H15 | 0.0866 | 0.8377 | 0.5850 | 0.069* | |
C16 | 0.1350 (4) | 0.6879 (3) | 0.5048 (3) | 0.0576 (9) | |
H16 | 0.0908 | 0.6816 | 0.4292 | 0.069* | |
C17 | 0.2049 (4) | 0.5973 (3) | 0.5191 (3) | 0.0462 (7) | |
C18 | 0.2051 (4) | 0.4961 (3) | 0.4253 (3) | 0.0554 (8) | |
H18 | 0.1600 | 0.4845 | 0.3477 | 0.066* | |
C19 | 0.2713 (4) | 0.4148 (3) | 0.4477 (3) | 0.0528 (7) | |
H19 | 0.2698 | 0.3466 | 0.3857 | 0.063* | |
C20 | 0.3419 (4) | 0.4346 (2) | 0.5653 (2) | 0.0431 (6) | |
H20 | 0.3882 | 0.3787 | 0.5798 | 0.052* | |
C21 | 0.2761 (3) | 0.6098 (2) | 0.6346 (2) | 0.0347 (5) | |
C22 | 0.2709 (3) | 0.7089 (2) | 0.7338 (2) | 0.0368 (5) |
U11 | U22 | U33 | U12 | U13 | U23 | |
Zn1 | 0.03197 (15) | 0.03128 (15) | 0.03090 (16) | 0.01282 (11) | 0.00887 (11) | 0.01442 (12) |
O1 | 0.0275 (8) | 0.0317 (9) | 0.0519 (11) | 0.0129 (7) | 0.0167 (7) | 0.0200 (8) |
O1W | 0.0366 (9) | 0.0456 (10) | 0.0323 (9) | 0.0045 (8) | 0.0085 (7) | 0.0186 (8) |
O2W | 0.0261 (8) | 0.0430 (10) | 0.0799 (15) | 0.0153 (8) | 0.0216 (9) | 0.0362 (11) |
O3W | 0.0400 (9) | 0.0313 (9) | 0.0369 (10) | 0.0082 (8) | 0.0113 (8) | 0.0115 (8) |
O2 | 0.0304 (9) | 0.0338 (9) | 0.0563 (12) | 0.0095 (8) | 0.0197 (8) | 0.0195 (9) |
O3 | 0.0370 (9) | 0.0304 (9) | 0.0369 (10) | −0.0007 (7) | 0.0087 (8) | 0.0090 (8) |
O4 | 0.0700 (14) | 0.0369 (10) | 0.0395 (11) | 0.0023 (10) | 0.0031 (10) | 0.0098 (9) |
O5 | 0.0393 (10) | 0.0349 (10) | 0.0579 (13) | −0.0018 (8) | −0.0010 (9) | 0.0182 (9) |
N1 | 0.0305 (10) | 0.0351 (11) | 0.0332 (11) | 0.0045 (9) | 0.0096 (8) | 0.0149 (9) |
N2 | 0.0415 (11) | 0.0355 (11) | 0.0391 (12) | 0.0166 (10) | 0.0111 (9) | 0.0173 (10) |
C1 | 0.0312 (11) | 0.0314 (11) | 0.0233 (11) | 0.0119 (10) | 0.0088 (9) | 0.0094 (9) |
C2 | 0.0315 (12) | 0.0305 (12) | 0.0412 (14) | 0.0131 (10) | 0.0098 (10) | 0.0135 (11) |
C3 | 0.0326 (12) | 0.0293 (12) | 0.0389 (13) | 0.0082 (10) | 0.0104 (10) | 0.0122 (11) |
C4 | 0.0298 (11) | 0.0283 (11) | 0.0362 (13) | 0.0078 (10) | 0.0095 (10) | 0.0081 (10) |
C5 | 0.0397 (13) | 0.0307 (12) | 0.0437 (15) | 0.0047 (11) | 0.0141 (11) | 0.0141 (11) |
C6 | 0.0421 (14) | 0.0350 (13) | 0.0389 (14) | 0.0089 (11) | 0.0143 (11) | 0.0144 (11) |
C7 | 0.0313 (12) | 0.0257 (11) | 0.0403 (13) | 0.0109 (10) | 0.0083 (10) | 0.0090 (10) |
C8 | 0.0350 (12) | 0.0283 (12) | 0.0453 (15) | 0.0047 (10) | 0.0112 (11) | 0.0140 (11) |
C9 | 0.0423 (14) | 0.0354 (13) | 0.0375 (14) | 0.0093 (11) | 0.0121 (11) | 0.0140 (11) |
C10 | 0.0375 (13) | 0.0279 (12) | 0.0428 (15) | 0.0140 (11) | 0.0056 (11) | 0.0088 (11) |
C11 | 0.079 (2) | 0.0516 (18) | 0.0494 (18) | 0.0348 (17) | 0.0232 (16) | 0.0190 (15) |
C12 | 0.099 (3) | 0.056 (2) | 0.079 (3) | 0.052 (2) | 0.034 (2) | 0.0220 (19) |
C13 | 0.065 (2) | 0.0548 (19) | 0.094 (3) | 0.0352 (17) | 0.022 (2) | 0.040 (2) |
C14 | 0.0349 (13) | 0.0506 (16) | 0.072 (2) | 0.0144 (13) | 0.0125 (13) | 0.0403 (16) |
C15 | 0.0395 (15) | 0.066 (2) | 0.083 (2) | 0.0134 (15) | 0.0094 (15) | 0.057 (2) |
C16 | 0.0354 (14) | 0.086 (2) | 0.066 (2) | 0.0094 (15) | 0.0071 (14) | 0.059 (2) |
C17 | 0.0311 (12) | 0.0660 (18) | 0.0423 (15) | 0.0023 (13) | 0.0079 (11) | 0.0344 (15) |
C18 | 0.0416 (15) | 0.079 (2) | 0.0339 (15) | −0.0026 (15) | 0.0082 (12) | 0.0269 (16) |
C19 | 0.0420 (15) | 0.0608 (19) | 0.0356 (15) | 0.0008 (14) | 0.0143 (12) | 0.0098 (14) |
C20 | 0.0377 (13) | 0.0421 (14) | 0.0410 (15) | 0.0057 (12) | 0.0150 (11) | 0.0135 (12) |
C21 | 0.0259 (11) | 0.0418 (13) | 0.0376 (13) | 0.0058 (10) | 0.0072 (9) | 0.0237 (11) |
C22 | 0.0274 (11) | 0.0388 (13) | 0.0466 (15) | 0.0093 (10) | 0.0081 (10) | 0.0250 (12) |
Zn1—O1W | 2.0443 (19) | C5—C6 | 1.373 (4) |
Zn1—O1 | 2.0598 (16) | C5—H5 | 0.9300 |
Zn1—O3W | 2.135 (2) | C6—C7 | 1.398 (4) |
Zn1—N2 | 2.155 (2) | C6—H7 | 0.9300 |
Zn1—N1 | 2.156 (2) | C7—C8 | 1.381 (4) |
Zn1—O2W | 2.1848 (19) | C7—C10 | 1.509 (4) |
O1—C1 | 1.272 (3) | C8—C9 | 1.390 (4) |
O1W—H1W1 | 0.847 (10) | C8—H8 | 0.9300 |
O1W—H1W2 | 0.84 (3) | C9—H9 | 0.9300 |
O2W—H2W1 | 0.85 (3) | C11—C12 | 1.397 (4) |
O2W—H2W2 | 0.84 (3) | C11—H11 | 0.9300 |
O3W—H3W1 | 0.853 (10) | C12—C13 | 1.353 (5) |
O3W—H3W2 | 0.85 (3) | C12—H12 | 0.9300 |
O2—C1 | 1.244 (3) | C13—C14 | 1.404 (5) |
O3—C4 | 1.364 (3) | C13—H13 | 0.9300 |
O3—C3 | 1.437 (3) | C14—C22 | 1.408 (4) |
O4—C10 | 1.244 (3) | C14—C15 | 1.432 (4) |
O5—C10 | 1.262 (3) | C15—C16 | 1.336 (5) |
N1—C20 | 1.319 (3) | C15—H15 | 0.9300 |
N1—C21 | 1.355 (3) | C16—C17 | 1.441 (4) |
N2—C11 | 1.312 (4) | C16—H16 | 0.9300 |
N2—C22 | 1.357 (3) | C17—C18 | 1.399 (5) |
C1—C2 | 1.517 (3) | C17—C21 | 1.409 (3) |
C2—C3 | 1.512 (3) | C18—C19 | 1.357 (5) |
C2—H1 | 0.9700 | C18—H18 | 0.9300 |
C2—H2 | 0.9700 | C19—C20 | 1.399 (4) |
C3—H3 | 0.9700 | C19—H19 | 0.9300 |
C3—H4 | 0.9700 | C20—H20 | 0.9300 |
C4—C9 | 1.381 (4) | C21—C22 | 1.435 (4) |
C4—C5 | 1.390 (4) | ||
O1W—Zn1—O1 | 95.99 (8) | C4—C5—H5 | 119.7 |
O1W—Zn1—O3W | 91.68 (8) | C5—C6—C7 | 120.7 (3) |
O1—Zn1—O3W | 90.86 (7) | C5—C6—H7 | 119.7 |
O1W—Zn1—N2 | 90.54 (9) | C7—C6—H7 | 119.7 |
O1—Zn1—N2 | 173.43 (8) | C8—C7—C6 | 118.1 (2) |
O3W—Zn1—N2 | 89.68 (8) | C8—C7—C10 | 120.8 (2) |
O1W—Zn1—N1 | 167.19 (8) | C6—C7—C10 | 121.0 (2) |
O1—Zn1—N1 | 95.91 (8) | C7—C8—C9 | 121.6 (2) |
O3W—Zn1—N1 | 92.87 (8) | C7—C8—H8 | 119.2 |
N2—Zn1—N1 | 77.52 (9) | C9—C8—H8 | 119.2 |
O1W—Zn1—O2W | 87.19 (9) | C4—C9—C8 | 119.6 (3) |
O1—Zn1—O2W | 86.15 (7) | C4—C9—H9 | 120.2 |
O3W—Zn1—O2W | 176.67 (7) | C8—C9—H9 | 120.2 |
N2—Zn1—O2W | 93.45 (8) | O4—C10—O5 | 125.6 (3) |
N1—Zn1—O2W | 88.90 (9) | O4—C10—C7 | 117.7 (2) |
C1—O1—Zn1 | 133.85 (16) | O5—C10—C7 | 116.7 (2) |
Zn1—O1W—H1W1 | 121 (2) | N2—C11—C12 | 122.7 (3) |
Zn1—O1W—H1W2 | 115 (2) | N2—C11—H11 | 118.7 |
H1W1—O1W—H1W2 | 110.3 (16) | C12—C11—H11 | 118.7 |
Zn1—O2W—H2W1 | 126 (2) | C13—C12—C11 | 119.7 (3) |
Zn1—O2W—H2W2 | 123 (2) | C13—C12—H12 | 120.2 |
H2W1—O2W—H2W2 | 110 (4) | C11—C12—H12 | 120.2 |
Zn1—O3W—H3W1 | 118 (2) | C12—C13—C14 | 119.6 (3) |
Zn1—O3W—H3W2 | 96 (2) | C12—C13—H13 | 120.2 |
H3W1—O3W—H3W2 | 109.1 (16) | C14—C13—H13 | 120.2 |
C4—O3—C3 | 117.65 (19) | C13—C14—C22 | 117.1 (3) |
C20—N1—C21 | 118.5 (2) | C13—C14—C15 | 124.0 (3) |
C20—N1—Zn1 | 128.33 (19) | C22—C14—C15 | 119.0 (3) |
C21—N1—Zn1 | 113.14 (17) | C16—C15—C14 | 121.3 (3) |
C11—N2—C22 | 118.5 (2) | C16—C15—H15 | 119.4 |
C11—N2—Zn1 | 128.2 (2) | C14—C15—H15 | 119.4 |
C22—N2—Zn1 | 113.17 (17) | C15—C16—C17 | 121.6 (3) |
O2—C1—O1 | 124.9 (2) | C15—C16—H16 | 119.2 |
O2—C1—C2 | 119.1 (2) | C17—C16—H16 | 119.2 |
O1—C1—C2 | 116.0 (2) | C18—C17—C21 | 117.2 (3) |
C3—C2—C1 | 113.5 (2) | C18—C17—C16 | 124.3 (3) |
C3—C2—H1 | 108.9 | C21—C17—C16 | 118.5 (3) |
C1—C2—H1 | 108.9 | C19—C18—C17 | 119.9 (3) |
C3—C2—H2 | 108.9 | C19—C18—H18 | 120.0 |
C1—C2—H2 | 108.9 | C17—C18—H18 | 120.0 |
H1—C2—H2 | 107.7 | C18—C19—C20 | 119.3 (3) |
O3—C3—C2 | 106.5 (2) | C18—C19—H19 | 120.3 |
O3—C3—H3 | 110.4 | C20—C19—H19 | 120.3 |
C2—C3—H3 | 110.4 | N1—C20—C19 | 122.7 (3) |
O3—C3—H4 | 110.4 | N1—C20—H20 | 118.7 |
C2—C3—H4 | 110.4 | C19—C20—H20 | 118.7 |
H3—C3—H4 | 108.6 | N1—C21—C17 | 122.4 (3) |
O3—C4—C9 | 124.6 (2) | N1—C21—C22 | 117.9 (2) |
O3—C4—C5 | 116.0 (2) | C17—C21—C22 | 119.8 (2) |
C9—C4—C5 | 119.4 (2) | N2—C22—C14 | 122.4 (3) |
C6—C5—C4 | 120.7 (2) | N2—C22—C21 | 117.7 (2) |
C6—C5—H5 | 119.7 | C14—C22—C21 | 119.9 (2) |
O1W—Zn1—O1—C1 | −95.5 (2) | C6—C7—C10—O4 | −7.4 (4) |
O3W—Zn1—O1—C1 | −3.7 (2) | C8—C7—C10—O5 | −5.9 (4) |
N1—Zn1—O1—C1 | 89.3 (2) | C6—C7—C10—O5 | 174.0 (2) |
O2W—Zn1—O1—C1 | 177.8 (2) | C22—N2—C11—C12 | −0.8 (5) |
O1W—Zn1—N1—C20 | −153.9 (3) | Zn1—N2—C11—C12 | 174.9 (3) |
O1—Zn1—N1—C20 | 4.3 (2) | N2—C11—C12—C13 | −0.8 (6) |
O3W—Zn1—N1—C20 | 95.5 (2) | C11—C12—C13—C14 | 2.2 (6) |
N2—Zn1—N1—C20 | −175.5 (2) | C12—C13—C14—C22 | −2.1 (5) |
O2W—Zn1—N1—C20 | −81.7 (2) | C12—C13—C14—C15 | 177.5 (3) |
O1W—Zn1—N1—C21 | 28.0 (4) | C13—C14—C15—C16 | −177.8 (3) |
O1—Zn1—N1—C21 | −173.77 (16) | C22—C14—C15—C16 | 1.8 (4) |
O3W—Zn1—N1—C21 | −82.61 (17) | C14—C15—C16—C17 | −0.4 (5) |
N2—Zn1—N1—C21 | 6.43 (16) | C15—C16—C17—C18 | 177.5 (3) |
O2W—Zn1—N1—C21 | 100.21 (16) | C15—C16—C17—C21 | −1.7 (4) |
O1W—Zn1—N2—C11 | 1.9 (3) | C21—C17—C18—C19 | 0.3 (4) |
O3W—Zn1—N2—C11 | −89.8 (3) | C16—C17—C18—C19 | −178.9 (3) |
N1—Zn1—N2—C11 | 177.2 (3) | C17—C18—C19—C20 | −1.2 (4) |
O2W—Zn1—N2—C11 | 89.1 (3) | C21—N1—C20—C19 | 0.7 (4) |
O1W—Zn1—N2—C22 | 177.79 (18) | Zn1—N1—C20—C19 | −177.37 (19) |
O3W—Zn1—N2—C22 | 86.11 (18) | C18—C19—C20—N1 | 0.7 (4) |
N1—Zn1—N2—C22 | −6.89 (17) | C20—N1—C21—C17 | −1.5 (4) |
O2W—Zn1—N2—C22 | −95.00 (19) | Zn1—N1—C21—C17 | 176.77 (19) |
Zn1—O1—C1—O2 | 4.9 (4) | C20—N1—C21—C22 | 176.5 (2) |
Zn1—O1—C1—C2 | −176.39 (16) | Zn1—N1—C21—C22 | −5.2 (3) |
O2—C1—C2—C3 | −143.6 (2) | C18—C17—C21—N1 | 1.1 (4) |
O1—C1—C2—C3 | 37.6 (3) | C16—C17—C21—N1 | −179.7 (2) |
C4—O3—C3—C2 | 174.05 (19) | C18—C17—C21—C22 | −176.9 (2) |
C1—C2—C3—O3 | 64.8 (3) | C16—C17—C21—C22 | 2.4 (4) |
C3—O3—C4—C9 | 2.0 (3) | C11—N2—C22—C14 | 0.9 (4) |
C3—O3—C4—C5 | −178.6 (2) | Zn1—N2—C22—C14 | −175.4 (2) |
O3—C4—C5—C6 | −179.8 (2) | C11—N2—C22—C21 | −177.1 (3) |
C9—C4—C5—C6 | −0.4 (4) | Zn1—N2—C22—C21 | 6.5 (3) |
C4—C5—C6—C7 | −0.1 (4) | C13—C14—C22—N2 | 0.5 (4) |
C5—C6—C7—C8 | 0.0 (4) | C15—C14—C22—N2 | −179.1 (2) |
C5—C6—C7—C10 | −179.9 (2) | C13—C14—C22—C21 | 178.5 (3) |
C6—C7—C8—C9 | 0.5 (4) | C15—C14—C22—C21 | −1.1 (4) |
C10—C7—C8—C9 | −179.5 (2) | N1—C21—C22—N2 | −0.9 (3) |
O3—C4—C9—C8 | −179.6 (2) | C17—C21—C22—N2 | 177.2 (2) |
C5—C4—C9—C8 | 1.0 (4) | N1—C21—C22—C14 | −179.0 (2) |
C7—C8—C9—C4 | −1.1 (4) | C17—C21—C22—C14 | −1.0 (4) |
C8—C7—C10—O4 | 172.6 (2) |
D—H···A | D—H | H···A | D···A | D—H···A |
O1W—H1W1···O5i | 0.85 (1) | 1.73 (1) | 2.566 (3) | 172 (3) |
O1W—H1W2···O1ii | 0.84 (3) | 2.07 (2) | 2.834 (3) | 150 (3) |
O2W—H2W1···O2iii | 0.85 (3) | 1.93 (3) | 2.775 (2) | 174 (3) |
O2W—H2W2···O5iv | 0.84 (3) | 2.03 (3) | 2.869 (3) | 176 (3) |
O3W—H3W1···O4i | 0.85 (1) | 1.84 (1) | 2.684 (3) | 173 (3) |
O3W—H3W2···O2 | 0.85 (3) | 1.89 (3) | 2.734 (3) | 170 (3) |
O3W—H3W2···O1 | 0.85 (3) | 2.56 (3) | 2.989 (3) | 113 (2) |
Symmetry codes: (i) x+1, y+1, z+1; (ii) −x+1, −y+1, −z+2; (iii) x−1, y, z; (iv) −x, −y, −z+1. |
Experimental details
Crystal data | |
Chemical formula | [Zn(C10H8O5)(C12H8N2)(H2O)3] |
Mr | 507.79 |
Crystal system, space group | Triclinic, P1 |
Temperature (K) | 295 |
a, b, c (Å) | 7.7101 (15), 12.987 (3), 13.059 (3) |
α, β, γ (°) | 113.31 (3), 103.62 (3), 100.99 (3) |
V (Å3) | 1106.4 (4) |
Z | 2 |
Radiation type | Mo Kα |
µ (mm−1) | 1.16 |
Crystal size (mm) | 0.34 × 0.24 × 0.20 |
Data collection | |
Diffractometer | Rigaku R-AXIS RAPID |
Absorption correction | Multi-scan (ABSCOR; Higashi, 1995) |
Tmin, Tmax | 0.694, 0.801 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 10928, 5015, 4188 |
Rint | 0.022 |
(sin θ/λ)max (Å−1) | 0.649 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.032, 0.101, 1.16 |
No. of reflections | 5015 |
No. of parameters | 316 |
No. of restraints | 9 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.39, −0.33 |
Computer programs: RAPID-AUTO (Rigaku, 1998), CrystalStructure (Rigaku/MSC 2002), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), ORTEPII (Johnson, 1976).
Zn1—O1W | 2.0443 (19) | Zn1—N2 | 2.155 (2) |
Zn1—O1 | 2.0598 (16) | Zn1—N1 | 2.156 (2) |
Zn1—O3W | 2.135 (2) | Zn1—O2W | 2.1848 (19) |
O1W—Zn1—O1 | 95.99 (8) | O3W—Zn1—N1 | 92.87 (8) |
O1W—Zn1—O3W | 91.68 (8) | N2—Zn1—N1 | 77.52 (9) |
O1—Zn1—O3W | 90.86 (7) | O1W—Zn1—O2W | 87.19 (9) |
O1W—Zn1—N2 | 90.54 (9) | O1—Zn1—O2W | 86.15 (7) |
O1—Zn1—N2 | 173.43 (8) | O3W—Zn1—O2W | 176.67 (7) |
O3W—Zn1—N2 | 89.68 (8) | N2—Zn1—O2W | 93.45 (8) |
O1W—Zn1—N1 | 167.19 (8) | N1—Zn1—O2W | 88.90 (9) |
O1—Zn1—N1 | 95.91 (8) |
D—H···A | D—H | H···A | D···A | D—H···A |
O1W—H1W1···O5i | 0.847 (10) | 1.725 (11) | 2.566 (3) | 172 (3) |
O1W—H1W2···O1ii | 0.84 (3) | 2.071 (18) | 2.834 (3) | 150 (3) |
O2W—H2W1···O2iii | 0.85 (3) | 1.93 (3) | 2.775 (2) | 174 (3) |
O2W—H2W2···O5iv | 0.84 (3) | 2.03 (3) | 2.869 (3) | 176 (3) |
O3W—H3W1···O4i | 0.853 (10) | 1.835 (11) | 2.684 (3) | 173 (3) |
O3W—H3W2···O2 | 0.85 (3) | 1.89 (3) | 2.734 (3) | 170 (3) |
O3W—H3W2···O1 | 0.85 (3) | 2.56 (3) | 2.989 (3) | 113 (2) |
Symmetry codes: (i) x+1, y+1, z+1; (ii) −x+1, −y+1, −z+2; (iii) x−1, y, z; (iv) −x, −y, −z+1. |
Our studies have addressed the metal derivatives of carboxyphenoxypropionic acids which are regarded as excellent candidates for the construction of supramolecular architectures. Thus, 3-(p-CPOPH2) may be not only multiple coordination possibilities, but also form regular hydrogen bonds by functioning as both a hydrogen bond donor and acceptor (Gao & Ng, 2006). Recently, we have reported the structures of cobalt(II) complex incorporating 3-(4-carboxylatophenoxy)propionate group, namely [Co(C10H9O5)2(C10H10O5)2(py)2], (Kong et al., 2007).
The molecular structure of the title complex is shown in Fig. 1. The 3-(p-CPOP)2- ligand coordinates in a monodentate fashion to the Zn atom through the carboxylate group. The Zn atom displays a distorted octahedral geometry involving one O atom of the 3-(4-carboxylatophenoxy)propionate group, two N atoms of 1,10-phenanthroline ligand and three water molecules. Furthermore, a three-dimensional supramolecular network is constructed via π-π stacking interactions between the 1,10-phenanthroline rings (centroid-centroid distance being 3.656 Å) and hydrogen-bonding interactions (Table 2).