supplementary materials

Diacetato{4'-[4-(benzyloxy)phenyl]-2,2':6',2''-terpyridine}zinc(II)
In the title compound, [Zn(CH3COO)2(C28H21N3O)], the ZnII ion is in a trigonal-bipyramidal ZnN3O2 coordination with a tridentate N-chelating 4'-[4-(benzyloxy)phenyl)-2,2':6',2''-terpyridine ligand in the equatorial position and two acetate anions in the axial positions. The three pyridine rings are approximately coplanar, with a maximum deviation of 0.03 Å from the mean plane. The phenoxy substituent makes a dihedral angle of 18.1 (2)° with the central pyridine ring. The benzyl group has a C-O-C-C torsion angle of 77.62 (8)° relative to the phenoxy ring. In the crystal, molecules are linked via C-H
O hydrogen bonds.
To a tetrahydrofuran solution (10 ml) of the ligand L (0.100 g, 0.241 mmol) was slowly added a methanolic solution (10 ml) of zinc acetate (0.044 g,
0.241 mmol). After stirring for 3 h at ambient temperature, a white solid was
collected by filtration and washed with MeOH. Colorless single crystals
suitable for X-ray determination were obtained by vapour diffusion of diethyl
ether into a methanol solution of the powder sample over the course of 5 days.
Aromatic H atoms were fixed at C—H distances of 0.93 Å and refined as riding
with Uiso(H) = 1.2Ueq(C). Other H atoms were positioned
geometrically and refined using a riding model with C—H = 0.96–0.97 Å and
with Uiso(H) = 1.5 Ueq(C). PLATON (Spek, 2009)
suggests a
(pseudo)-centrosymmetric structure in space group P21/c.
However, attempts to refine the structure in the centrosymmetric space group
led to significantly higher residuals, high anisotropic displacement parameters
and some disordered atoms. The crystal under investigation was refined as an
inversion twin with a twin component ration of ca. 9:1.
Data collection: RAPID-AUTO (Rigaku, 1998); cell refinement: RAPID-AUTO (Rigaku, 1998); data reduction: CrystalClear (Rigaku/MSC, 2002); 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).
Diacetato{4'-[4-(benzyloxy)phenyl]-2,2':6',2''-terpyridine}zinc(II)
top
Crystal data top
| [Zn(C2H3O2)2(C28H21N3O)] | F(000) = 620 |
| Mr = 598.94 | Dx = 1.455 Mg m−3 |
| Monoclinic, Pn | Mo Kα radiation, λ = 0.71073 Å |
| Hall symbol: P -2yac | Cell parameters from 8985 reflections |
| a = 8.3959 (17) Å | θ = 3.1–27.4° |
| b = 15.564 (3) Å | µ = 0.95 mm−1 |
| c = 10.702 (2) Å | T = 291 K |
| β = 102.23 (3)° | Block, colorless |
| V = 1366.7 (5) Å3 | 0.26 × 0.23 × 0.21 mm |
| Z = 2 | |
Data collection top
Rigaku R-AXIS RAPID diffractometer | 5859 independent reflections |
| Radiation source: fine-focus sealed tube | 3538 reflections with I > 2σ(I) |
| graphite | Rint = 0.043 |
| ω scan | θmax = 27.4°, θmin = 3.1° |
Absorption correction: multi-scan (ABSCOR; Higashi, 1995) | h = −10→10 |
| Tmin = 0.791, Tmax = 0.826 | k = −20→20 |
| 13194 measured reflections | l = −13→13 |
Refinement top
| 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)] = 0.037 | H-atom parameters constrained |
| wR(F2) = 0.106 | w = 1/[σ2(Fo2) + (0.0503P)2] where P = (Fo2 + 2Fc2)/3 |
| S = 0.98 | (Δ/σ)max = 0.001 |
| 5859 reflections | Δρmax = 0.48 e Å−3 |
| 373 parameters | Δρmin = −0.56 e Å−3 |
| 2 restraints | Absolute structure: Flack (1983), 2733 Friedel pairs |
| Primary atom site location: structure-invariant direct methods | Flack parameter: 0.108 (13) |
Crystal data top
| [Zn(C2H3O2)2(C28H21N3O)] | V = 1366.7 (5) Å3 |
| Mr = 598.94 | Z = 2 |
| Monoclinic, Pn | Mo Kα radiation |
| a = 8.3959 (17) Å | µ = 0.95 mm−1 |
| b = 15.564 (3) Å | T = 291 K |
| c = 10.702 (2) Å | 0.26 × 0.23 × 0.21 mm |
| β = 102.23 (3)° | |
Data collection top
Rigaku R-AXIS RAPID diffractometer | 5859 independent reflections |
Absorption correction: multi-scan (ABSCOR; Higashi, 1995) | 3538 reflections with I > 2σ(I) |
| Tmin = 0.791, Tmax = 0.826 | Rint = 0.043 |
| 13194 measured reflections | θmax = 27.4° |
Refinement top
| R[F2 > 2σ(F2)] = 0.037 | H-atom parameters constrained |
| wR(F2) = 0.106 | Δρmax = 0.48 e Å−3 |
| S = 0.98 | Δρmin = −0.56 e Å−3 |
| 5859 reflections | Absolute structure: Flack (1983), 2733 Friedel pairs |
| 373 parameters | Flack parameter: 0.108 (13) |
| 2 restraints | |
Special details top
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. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top| | x | y | z | Uiso*/Ueq | |
| C1 | 0.8831 (7) | 0.3046 (4) | 0.9729 (6) | 0.0593 (17) | |
| H1 | 0.8640 | 0.2457 | 0.9695 | 0.071* | |
| C2 | 1.0368 (7) | 0.3342 (4) | 1.0203 (7) | 0.071 (2) | |
| H2 | 1.1225 | 0.2956 | 1.0432 | 0.085* | |
| C3 | 1.0655 (6) | 0.4200 (4) | 1.0342 (5) | 0.0584 (15) | |
| H3 | 1.1690 | 0.4404 | 1.0707 | 0.070* | |
| C4 | 0.9378 (6) | 0.4766 (4) | 0.9929 (5) | 0.0547 (14) | |
| H4 | 0.9538 | 0.5357 | 0.9989 | 0.066* | |
| C5 | 0.7855 (6) | 0.4424 (3) | 0.9424 (5) | 0.0457 (12) | |
| C6 | 0.6379 (6) | 0.4966 (3) | 0.8920 (5) | 0.0436 (13) | |
| C7 | 0.6359 (6) | 0.5845 (3) | 0.8898 (5) | 0.0505 (14) | |
| H7 | 0.7320 | 0.6150 | 0.9187 | 0.061* | |
| C8 | 0.4896 (7) | 0.6291 (2) | 0.8440 (7) | 0.0441 (10) | |
| C9 | 0.3513 (6) | 0.5806 (3) | 0.8006 (5) | 0.0478 (13) | |
| H9 | 0.2518 | 0.6076 | 0.7702 | 0.057* | |
| C10 | 0.3608 (6) | 0.4912 (3) | 0.8023 (5) | 0.0423 (13) | |
| C11 | 0.2215 (6) | 0.4320 (3) | 0.7578 (5) | 0.0475 (13) | |
| C12 | 0.0654 (6) | 0.4599 (4) | 0.7014 (5) | 0.0571 (15) | |
| H12 | 0.0426 | 0.5181 | 0.6880 | 0.068* | |
| C13 | −0.0562 (7) | 0.3980 (4) | 0.6655 (6) | 0.0645 (17) | |
| H13 | −0.1622 | 0.4148 | 0.6292 | 0.077* | |
| C14 | −0.0200 (7) | 0.3134 (4) | 0.6834 (6) | 0.0600 (16) | |
| H14 | −0.0997 | 0.2718 | 0.6585 | 0.072* | |
| C15 | 0.1373 (7) | 0.2905 (4) | 0.7393 (6) | 0.0615 (16) | |
| H15 | 0.1606 | 0.2325 | 0.7536 | 0.074* | |
| C16 | 0.4862 (7) | 0.7251 (2) | 0.8434 (6) | 0.0482 (11) | |
| C17 | 0.6114 (7) | 0.7729 (4) | 0.9184 (6) | 0.0603 (15) | |
| H17 | 0.6995 | 0.7449 | 0.9696 | 0.072* | |
| C18 | 0.6047 (7) | 0.8626 (4) | 0.9167 (6) | 0.0638 (16) | |
| H18 | 0.6878 | 0.8943 | 0.9676 | 0.077* | |
| C19 | 0.4755 (6) | 0.9042 (3) | 0.8400 (6) | 0.0562 (14) | |
| C20 | 0.3523 (6) | 0.8577 (3) | 0.7660 (6) | 0.0611 (15) | |
| H20 | 0.2646 | 0.8859 | 0.7146 | 0.073* | |
| C21 | 0.3582 (6) | 0.7699 (3) | 0.7674 (5) | 0.0573 (14) | |
| H21 | 0.2740 | 0.7392 | 0.7161 | 0.069* | |
| C22 | 0.3569 (6) | 1.0418 (3) | 0.7676 (6) | 0.0794 (14) | |
| H22A | 0.3336 | 1.0169 | 0.6825 | 0.095* | |
| H22B | 0.3954 | 1.1000 | 0.7606 | 0.095* | |
| C23 | 0.2019 (6) | 1.0450 (3) | 0.8165 (5) | 0.0635 (13) | |
| C24 | 0.2036 (7) | 1.0670 (3) | 0.9414 (5) | 0.0758 (14) | |
| H24 | 0.3027 | 1.0775 | 0.9972 | 0.091* | |
| C25 | 0.0619 (8) | 1.0737 (4) | 0.9849 (7) | 0.0897 (18) | |
| H25 | 0.0673 | 1.0886 | 1.0699 | 0.108* | |
| C26 | −0.0850 (8) | 1.0595 (4) | 0.9082 (8) | 0.0888 (19) | |
| H26 | −0.1798 | 1.0633 | 0.9397 | 0.107* | |
| C27 | −0.0913 (7) | 1.0392 (4) | 0.7829 (8) | 0.100 (2) | |
| H27 | −0.1920 | 1.0308 | 0.7283 | 0.120* | |
| C28 | 0.0516 (8) | 1.0309 (4) | 0.7351 (6) | 0.0859 (18) | |
| H28 | 0.0456 | 1.0161 | 0.6500 | 0.103* | |
| C29 | 0.4567 (6) | 0.2751 (4) | 1.0846 (6) | 0.0572 (15) | |
| C30 | 0.4161 (8) | 0.2233 (5) | 1.1989 (7) | 0.100 (2) | |
| H30A | 0.3133 | 0.1947 | 1.1716 | 0.149* | |
| H30B | 0.4099 | 0.2619 | 1.2676 | 0.149* | |
| H30C | 0.4999 | 0.1815 | 1.2276 | 0.149* | |
| C31 | 0.5525 (6) | 0.2511 (4) | 0.6214 (6) | 0.0605 (15) | |
| C32 | 0.5948 (9) | 0.1794 (4) | 0.5365 (6) | 0.086 (2) | |
| H32A | 0.4985 | 0.1626 | 0.4757 | 0.129* | |
| H32B | 0.6371 | 0.1309 | 0.5885 | 0.129* | |
| H32C | 0.6754 | 0.1997 | 0.4919 | 0.129* | |
| N1 | 0.7606 (5) | 0.3578 (3) | 0.9319 (5) | 0.0481 (11) | |
| N2 | 0.5019 (6) | 0.45091 (16) | 0.8450 (5) | 0.0440 (7) | |
| N3 | 0.2591 (6) | 0.3473 (3) | 0.7745 (5) | 0.0523 (12) | |
| O1 | 0.4850 (6) | 0.99246 (16) | 0.8480 (6) | 0.0784 (10) | |
| O2 | 0.4764 (5) | 0.2367 (3) | 0.9965 (4) | 0.0664 (11) | |
| O3 | 0.4605 (6) | 0.3537 (3) | 1.1031 (5) | 0.0977 (14) | |
| O4 | 0.5539 (5) | 0.2307 (2) | 0.7346 (4) | 0.0696 (11) | |
| O5 | 0.5191 (7) | 0.3222 (3) | 0.5782 (5) | 0.1088 (18) | |
| Zn1 | 0.50944 (8) | 0.31689 (2) | 0.85645 (8) | 0.05098 (14) | |
Atomic displacement parameters (Å2) top| | U11 | U22 | U33 | U12 | U13 | U23 |
| C1 | 0.049 (3) | 0.046 (3) | 0.082 (4) | 0.007 (2) | 0.012 (3) | 0.009 (3) |
| C2 | 0.042 (3) | 0.078 (4) | 0.092 (5) | 0.017 (3) | 0.010 (3) | 0.010 (3) |
| C3 | 0.042 (3) | 0.066 (3) | 0.063 (3) | −0.001 (3) | 0.002 (2) | 0.000 (3) |
| C4 | 0.043 (3) | 0.056 (3) | 0.065 (3) | 0.001 (2) | 0.011 (2) | −0.004 (3) |
| C5 | 0.040 (3) | 0.044 (3) | 0.056 (3) | −0.001 (2) | 0.017 (2) | 0.000 (2) |
| C6 | 0.039 (3) | 0.037 (3) | 0.056 (3) | 0.003 (2) | 0.013 (2) | −0.005 (2) |
| C7 | 0.046 (3) | 0.042 (3) | 0.064 (3) | −0.009 (2) | 0.013 (2) | −0.003 (2) |
| C8 | 0.043 (3) | 0.0359 (16) | 0.055 (3) | 0.003 (2) | 0.013 (2) | 0.001 (3) |
| C9 | 0.037 (3) | 0.041 (3) | 0.065 (3) | 0.000 (2) | 0.010 (2) | 0.000 (2) |
| C10 | 0.040 (3) | 0.037 (3) | 0.049 (3) | 0.004 (2) | 0.009 (2) | −0.003 (2) |
| C11 | 0.040 (3) | 0.047 (3) | 0.057 (3) | −0.004 (2) | 0.012 (2) | 0.003 (2) |
| C12 | 0.050 (3) | 0.051 (3) | 0.068 (4) | 0.004 (2) | 0.007 (3) | 0.003 (3) |
| C13 | 0.039 (3) | 0.071 (4) | 0.081 (4) | −0.005 (3) | 0.007 (2) | −0.001 (3) |
| C14 | 0.048 (3) | 0.055 (3) | 0.073 (4) | −0.014 (2) | 0.005 (3) | −0.009 (2) |
| C15 | 0.053 (3) | 0.045 (3) | 0.088 (5) | −0.011 (3) | 0.017 (3) | 0.001 (3) |
| C16 | 0.051 (3) | 0.0395 (18) | 0.057 (3) | −0.007 (2) | 0.018 (2) | −0.007 (3) |
| C17 | 0.053 (3) | 0.044 (3) | 0.080 (4) | 0.002 (2) | 0.005 (3) | −0.002 (3) |
| C18 | 0.050 (3) | 0.043 (3) | 0.093 (4) | −0.004 (2) | 0.004 (3) | −0.010 (3) |
| C19 | 0.050 (4) | 0.0365 (19) | 0.082 (4) | −0.002 (2) | 0.014 (3) | 0.000 (3) |
| C20 | 0.052 (3) | 0.039 (3) | 0.092 (4) | 0.001 (2) | 0.014 (3) | 0.005 (3) |
| C21 | 0.053 (3) | 0.039 (3) | 0.077 (4) | −0.001 (2) | 0.008 (2) | 0.007 (3) |
| C22 | 0.082 (4) | 0.039 (2) | 0.122 (4) | 0.002 (2) | 0.031 (3) | 0.009 (3) |
| C23 | 0.061 (3) | 0.034 (2) | 0.093 (4) | 0.007 (2) | 0.011 (3) | 0.007 (2) |
| C24 | 0.065 (3) | 0.065 (3) | 0.095 (4) | −0.001 (3) | 0.013 (3) | 0.000 (3) |
| C25 | 0.088 (5) | 0.080 (4) | 0.109 (5) | 0.003 (3) | 0.038 (4) | −0.008 (3) |
| C26 | 0.081 (5) | 0.067 (4) | 0.124 (6) | −0.004 (3) | 0.036 (4) | −0.001 (4) |
| C27 | 0.059 (4) | 0.087 (5) | 0.144 (7) | 0.006 (3) | 0.001 (4) | 0.009 (4) |
| C28 | 0.082 (4) | 0.080 (4) | 0.090 (5) | 0.000 (3) | 0.008 (3) | 0.001 (3) |
| C29 | 0.031 (2) | 0.059 (4) | 0.074 (4) | −0.007 (2) | −0.006 (2) | 0.012 (3) |
| C30 | 0.076 (4) | 0.106 (6) | 0.113 (5) | −0.001 (4) | 0.013 (4) | 0.036 (5) |
| C31 | 0.045 (3) | 0.048 (3) | 0.084 (4) | 0.003 (2) | 0.002 (2) | −0.002 (3) |
| C32 | 0.089 (4) | 0.094 (5) | 0.074 (4) | 0.022 (4) | 0.017 (3) | −0.017 (3) |
| N1 | 0.040 (2) | 0.037 (2) | 0.071 (3) | 0.0050 (19) | 0.020 (2) | 0.000 (2) |
| N2 | 0.0421 (15) | 0.0334 (13) | 0.056 (2) | −0.001 (2) | 0.0103 (14) | −0.002 (2) |
| N3 | 0.047 (3) | 0.040 (2) | 0.068 (3) | 0.000 (2) | 0.010 (2) | −0.002 (2) |
| O1 | 0.062 (3) | 0.0335 (13) | 0.141 (3) | −0.0014 (18) | 0.024 (2) | 0.000 (3) |
| O2 | 0.072 (3) | 0.049 (2) | 0.083 (3) | −0.0032 (19) | 0.027 (2) | 0.004 (2) |
| O3 | 0.113 (3) | 0.073 (3) | 0.112 (3) | −0.017 (3) | 0.034 (3) | −0.019 (3) |
| O4 | 0.078 (3) | 0.049 (2) | 0.080 (3) | 0.008 (2) | 0.014 (2) | −0.001 (2) |
| O5 | 0.138 (5) | 0.077 (3) | 0.118 (4) | 0.024 (3) | 0.042 (3) | 0.026 (3) |
| Zn1 | 0.0465 (2) | 0.0366 (2) | 0.0702 (3) | 0.0007 (4) | 0.01314 (18) | 0.0003 (4) |
Geometric parameters (Å, °) top
| C1—N1 | 1.320 (7) | C19—C20 | 1.369 (7) |
| C1—C2 | 1.363 (9) | C19—O1 | 1.377 (5) |
| C1—H1 | 0.9300 | C20—C21 | 1.369 (8) |
| C2—C3 | 1.359 (8) | C20—H20 | 0.9300 |
| C2—H2 | 0.9300 | C21—H21 | 0.9300 |
| C3—C4 | 1.385 (7) | C22—O1 | 1.448 (6) |
| C3—H3 | 0.9300 | C22—C23 | 1.503 (7) |
| C4—C5 | 1.385 (7) | C22—H22A | 0.9700 |
| C4—H4 | 0.9300 | C22—H22B | 0.9700 |
| C5—N1 | 1.334 (7) | C23—C24 | 1.377 (7) |
| C5—C6 | 1.503 (7) | C23—C28 | 1.391 (7) |
| C6—N2 | 1.349 (6) | C24—C25 | 1.370 (8) |
| C6—C7 | 1.368 (8) | C24—H24 | 0.9300 |
| C7—C8 | 1.406 (7) | C25—C26 | 1.347 (8) |
| C7—H7 | 0.9300 | C25—H25 | 0.9300 |
| C8—C9 | 1.381 (7) | C26—C27 | 1.367 (9) |
| C8—C16 | 1.494 (5) | C26—H26 | 0.9300 |
| C9—C10 | 1.394 (8) | C27—C28 | 1.406 (9) |
| C9—H9 | 0.9300 | C27—H27 | 0.9300 |
| C10—N2 | 1.333 (6) | C28—H28 | 0.9300 |
| C10—C11 | 1.486 (7) | C29—O2 | 1.158 (6) |
| C11—N3 | 1.359 (7) | C29—O3 | 1.238 (7) |
| C11—C12 | 1.391 (7) | C29—C30 | 1.562 (8) |
| C12—C13 | 1.397 (7) | C30—H30A | 0.9600 |
| C12—H12 | 0.9300 | C30—H30B | 0.9600 |
| C13—C14 | 1.355 (8) | C30—H30C | 0.9600 |
| C13—H13 | 0.9300 | C31—O5 | 1.209 (7) |
| C14—C15 | 1.376 (8) | C31—O4 | 1.249 (7) |
| C14—H14 | 0.9300 | C31—C32 | 1.527 (8) |
| C15—N3 | 1.344 (7) | C32—H32A | 0.9600 |
| C15—H15 | 0.9300 | C32—H32B | 0.9600 |
| C16—C21 | 1.390 (7) | C32—H32C | 0.9600 |
| C16—C17 | 1.394 (7) | Zn1—N1 | 2.187 (4) |
| C17—C18 | 1.399 (9) | Zn1—N2 | 2.090 (3) |
| C17—H17 | 0.9300 | Zn1—N3 | 2.151 (5) |
| C18—C19 | 1.376 (7) | Zn1—O2 | 2.014 (4) |
| C18—H18 | 0.9300 | Zn1—O4 | 1.961 (4) |
| | | |
| N1—C1—C2 | 121.4 (6) | O1—C22—H22A | 108.9 |
| N1—C1—H1 | 119.3 | C23—C22—H22A | 108.9 |
| C2—C1—H1 | 119.3 | O1—C22—H22B | 108.9 |
| C3—C2—C1 | 120.3 (6) | C23—C22—H22B | 108.9 |
| C3—C2—H2 | 119.9 | H22A—C22—H22B | 107.7 |
| C1—C2—H2 | 119.9 | C24—C23—C28 | 118.0 (5) |
| C2—C3—C4 | 118.8 (5) | C24—C23—C22 | 121.0 (5) |
| C2—C3—H3 | 120.6 | C28—C23—C22 | 120.9 (5) |
| C4—C3—H3 | 120.6 | C25—C24—C23 | 121.1 (5) |
| C5—C4—C3 | 117.9 (6) | C25—C24—H24 | 119.4 |
| C5—C4—H4 | 121.0 | C23—C24—H24 | 119.4 |
| C3—C4—H4 | 121.0 | C26—C25—C24 | 122.0 (7) |
| N1—C5—C4 | 121.8 (5) | C26—C25—H25 | 119.0 |
| N1—C5—C6 | 115.0 (4) | C24—C25—H25 | 119.0 |
| C4—C5—C6 | 123.2 (5) | C25—C26—C27 | 118.4 (6) |
| N2—C6—C7 | 121.0 (5) | C25—C26—H26 | 120.8 |
| N2—C6—C5 | 113.9 (4) | C27—C26—H26 | 120.8 |
| C7—C6—C5 | 125.1 (5) | C26—C27—C28 | 121.3 (5) |
| C6—C7—C8 | 120.4 (5) | C26—C27—H27 | 119.3 |
| C6—C7—H7 | 119.8 | C28—C27—H27 | 119.3 |
| C8—C7—H7 | 119.8 | C23—C28—C27 | 119.2 (6) |
| C9—C8—C7 | 117.3 (3) | C23—C28—H28 | 120.4 |
| C9—C8—C16 | 122.1 (5) | C27—C28—H28 | 120.4 |
| C7—C8—C16 | 120.6 (5) | O2—C29—O3 | 129.6 (6) |
| C8—C9—C10 | 120.0 (5) | O2—C29—C30 | 117.6 (5) |
| C8—C9—H9 | 120.0 | O3—C29—C30 | 112.8 (6) |
| C10—C9—H9 | 120.0 | C29—C30—H30A | 109.5 |
| N2—C10—C9 | 121.2 (5) | C29—C30—H30B | 109.5 |
| N2—C10—C11 | 113.6 (5) | H30A—C30—H30B | 109.5 |
| C9—C10—C11 | 125.2 (5) | C29—C30—H30C | 109.5 |
| N3—C11—C12 | 122.1 (5) | H30A—C30—H30C | 109.5 |
| N3—C11—C10 | 114.4 (4) | H30B—C30—H30C | 109.5 |
| C12—C11—C10 | 123.4 (5) | O5—C31—O4 | 123.8 (6) |
| C11—C12—C13 | 118.1 (6) | O5—C31—C32 | 120.4 (7) |
| C11—C12—H12 | 121.0 | O4—C31—C32 | 115.8 (5) |
| C13—C12—H12 | 121.0 | C31—C32—H32A | 109.5 |
| C14—C13—C12 | 120.1 (5) | C31—C32—H32B | 109.5 |
| C14—C13—H13 | 119.9 | H32A—C32—H32B | 109.5 |
| C12—C13—H13 | 119.9 | C31—C32—H32C | 109.5 |
| C13—C14—C15 | 118.6 (6) | H32A—C32—H32C | 109.5 |
| C13—C14—H14 | 120.7 | H32B—C32—H32C | 109.5 |
| C15—C14—H14 | 120.7 | C1—N1—C5 | 119.6 (5) |
| N3—C15—C14 | 123.7 (6) | C1—N1—Zn1 | 124.2 (4) |
| N3—C15—H15 | 118.1 | C5—N1—Zn1 | 116.1 (3) |
| C14—C15—H15 | 118.1 | C10—N2—C6 | 120.0 (3) |
| C21—C16—C17 | 117.7 (4) | C10—N2—Zn1 | 120.2 (4) |
| C21—C16—C8 | 121.0 (5) | C6—N2—Zn1 | 119.5 (4) |
| C17—C16—C8 | 121.3 (5) | C15—N3—C11 | 117.3 (5) |
| C16—C17—C18 | 120.2 (5) | C15—N3—Zn1 | 126.1 (4) |
| C16—C17—H17 | 119.9 | C11—N3—Zn1 | 116.6 (3) |
| C18—C17—H17 | 119.9 | C19—O1—C22 | 117.8 (4) |
| C19—C18—C17 | 120.1 (5) | C29—O2—Zn1 | 110.5 (4) |
| C19—C18—H18 | 119.9 | C31—O4—Zn1 | 120.5 (4) |
| C17—C18—H18 | 119.9 | O4—Zn1—O2 | 98.42 (13) |
| C20—C19—C18 | 120.0 (4) | O4—Zn1—N2 | 130.6 (2) |
| C20—C19—O1 | 126.1 (5) | O2—Zn1—N2 | 130.9 (2) |
| C18—C19—O1 | 113.8 (5) | O4—Zn1—N3 | 100.76 (19) |
| C21—C20—C19 | 120.0 (5) | O2—Zn1—N3 | 99.39 (18) |
| C21—C20—H20 | 120.0 | N2—Zn1—N3 | 75.02 (19) |
| C19—C20—H20 | 120.0 | N4—Zn1—N1 | 98.04 (17) |
| C20—C21—C16 | 122.0 (5) | O2—Zn1—N1 | 100.36 (18) |
| C20—C21—H21 | 119.0 | N2—Zn1—N1 | 75.28 (18) |
| C16—C21—H21 | 119.0 | N3—Zn1—N1 | 150.30 (11) |
| O1—C22—C23 | 113.5 (5) | | |
Hydrogen-bond geometry (Å, °) top
| D—H···A | D—H | H···A | D···A | D—H···A |
| C4—H4···O5i | 0.93 | 2.39 | 3.293 (7) | 163 |
| C12—H12···O3ii | 0.93 | 2.24 | 3.147 (7) | 165 |
| C22—H22B···O4iii | 0.97 | 2.48 | 3.429 (6) | 166 |
| Symmetry codes: (i) x+1/2, −y+1, z+1/2; (ii) x−1/2, −y+1, z−1/2; (iii) x, y+1, z. |
Table 1
Selected geometric parameters (Å) top| Zn1—N1 | 2.187 (4) | Zn1—O2 | 2.014 (4) |
| Zn1—N2 | 2.090 (3) | Zn1—O4 | 1.961 (4) |
| Zn1—N3 | 2.151 (5) | | |
Table 2
Hydrogen-bond geometry (Å, °) top
| D—H···A | D—H | H···A | D···A | D—H···A |
| C4—H4···O5i | 0.93 | 2.39 | 3.293 (7) | 163 |
| C12—H12···O3ii | 0.93 | 2.24 | 3.147 (7) | 165 |
| C22—H22B···O4iii | 0.97 | 2.48 | 3.429 (6) | 166 |
| Symmetry codes: (i) x+1/2, −y+1, z+1/2; (ii) x−1/2, −y+1, z−1/2; (iii) x, y+1, z. |
The authors thank Dr Guang Feng Hou for the single-crystal analysis.
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Functionalized terpyridines are interesting materials (Heller & Schubert, 2003). 2,2':6',2"-terpyridine and its derivatives have been used as key building blocks in supramolecular frameworks (Duprez et al., 2005). We report here the crystal structure of the title compound, (I).
In the molecular structure of (I) (Fig. 1), the three pyridine rings are approximately coplanar (max. deviation from the mean plane 0.03 Å). The ZnII ion is in a trigonal-bipyramidal coordination by a neutral tridentate 4'-[4-(benzyloxy)phenyl)-2,2':6',2"-terpyridine ligand in equatorial and two acetate anions in axial positions (Table 1). The phenoxy substituent makes a dihedral angle of 18.1 (2)° with the central pyridine ring. The torsion angle between the benzoyl group and the attached phenoxy ring, defined by atoms C19—O01—C22—C23, is 77.6 (7)°.
Molecules of (I) are linked via O—H···C hydrogen bonds, as shown in Fig. 2. Molecules associate via C(22)—H(22B)···O(4)#3 interactions, forming a chain along the b axis. Adjacent chains are interconnected via C(4)—H(4)···O(5)#1 and C(12)—H(12)···O(3)#2 interactions, leading to the formation of a two dimensional network (Table 2).
In the structure of a similar ligand molecule (Anthonysamy et al., 2007) a trans-trans arrangement of the pyridine rings about the interannular C—C bonds is observed.