Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270105018044/av1245sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S0108270105018044/av1245Isup2.hkl |
CCDC reference: 278545
For the preparation of the ligand, 2-hydroxy-1-naphthaldehyde (1.72 g, 10 mmol) and o-anisidine (1.23 g, 10 mmol) were dissolved in ethanol (40 ml) and the solution was refluxed for 1 h. The resulting yellow product was filtered off, washed with ethanol and dried in vacuo (yield 2.12 g, 76.5%). Elemental analysis, found (calculated) for C18H15NO2: C 77.86 (77.96), H 5.68 (5.45), N 5.00 (5.05)%. The title compound was prepared by mixing zinc(II) acetate dihydrate (0.25 g, 1.14 mmol), the above ligand (0.63 g, 2.28 mmol) and triethylamine (0.23 g, 2.28 mmol) in ethanol (45 ml). After refluxing for 3 h, the reaction mixture was left to stand at room temperature for about a week. Only a few yellow single crystals of (I) were obtained. After a period of time, the crystals deteriorated into a yellow powder. Elemental analysis, found (calculated) for C36H28N2O4Zn: C 70.28 (69.96), H 5.04 (4.57), N 4.32 (4.53)%. Elemental analysis (CHN) was performed at the Central Analytical Laboratory of the Ruđer Bošković Institute, Zagreb.
All H atoms were positioned geometrically, each riding on their carrier atom, with C—H distances in the range 0.93–0.97 Å and an O—H distance of 0.82 Å, and with Uiso(H) = 1.5 (for methyl and hydroxyl H atoms) or 1.2 (for methylene and aromatic H atoms) times Ueq of the parent atom. [Please check added text.]
Data collection: STADI4 (Stoe & Cie, 1995); cell refinement: STADI4; data reduction: X-RED (Stoe & Cie, 1995); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: SHELXL97.
Fig. 1. A plot of the title compound. Displacement ellipsoids are drawn at the 50% probability level. |
[Zn(C18H14NO2)2]·C2H6O | Z = 2 |
Mr = 664.06 | F(000) = 692 |
Triclinic, P1 | Dx = 1.352 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 10.2078 (15) Å | Cell parameters from 60 reflections |
b = 10.9122 (14) Å | θ = 10.2–18.0° |
c = 16.7214 (10) Å | µ = 0.80 mm−1 |
α = 96.550 (16)° | T = 295 K |
β = 98.113 (8)° | Needle, yellow |
γ = 115.592 (12)° | 0.58 × 0.11 × 0.09 mm |
V = 1630.8 (4) Å3 |
Philips PW1100 upgraded by Stoe diffractometer | 5673 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.091 |
Graphite monochromator | θmax = 30.0°, θmin = 2.3° |
ω scans | h = −14→14 |
Absorption correction: ψ scan X-RED (Stoe & Cie, 1995) | k = −15→15 |
Tmin = 0.90, Tmax = 0.93 | l = 0→23 |
9774 measured reflections | 5 standard reflections every 120 min |
9462 independent reflections | intensity decay: 4.1% |
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)] = 0.056 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.165 | H-atom parameters constrained |
S = 1.03 | w = 1/[σ2(Fo2) + (0.1019P)2 + 0.0196P] where P = (Fo2 + 2Fc2)/3 |
9462 reflections | (Δ/σ)max < 0.001 |
419 parameters | Δρmax = 0.69 e Å−3 |
0 restraints | Δρmin = −0.63 e Å−3 |
[Zn(C18H14NO2)2]·C2H6O | γ = 115.592 (12)° |
Mr = 664.06 | V = 1630.8 (4) Å3 |
Triclinic, P1 | Z = 2 |
a = 10.2078 (15) Å | Mo Kα radiation |
b = 10.9122 (14) Å | µ = 0.80 mm−1 |
c = 16.7214 (10) Å | T = 295 K |
α = 96.550 (16)° | 0.58 × 0.11 × 0.09 mm |
β = 98.113 (8)° |
Philips PW1100 upgraded by Stoe diffractometer | 5673 reflections with I > 2σ(I) |
Absorption correction: ψ scan X-RED (Stoe & Cie, 1995) | Rint = 0.091 |
Tmin = 0.90, Tmax = 0.93 | 5 standard reflections every 120 min |
9774 measured reflections | intensity decay: 4.1% |
9462 independent reflections |
R[F2 > 2σ(F2)] = 0.056 | 0 restraints |
wR(F2) = 0.165 | H-atom parameters constrained |
S = 1.03 | Δρmax = 0.69 e Å−3 |
9462 reflections | Δρmin = −0.63 e Å−3 |
419 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 | 0.97035 (3) | 0.64365 (3) | 0.723042 (17) | 0.05448 (12) | |
O11 | 0.9710 (2) | 0.7663 (2) | 0.64536 (12) | 0.0720 (5) | |
O12 | 0.8677 (2) | 0.49016 (19) | 0.82038 (11) | 0.0663 (5) | |
O21 | 1.1768 (2) | 0.69808 (18) | 0.77828 (11) | 0.0627 (4) | |
O22 | 0.7029 (2) | 0.4771 (2) | 0.64923 (11) | 0.0685 (5) | |
O31 | 0.3442 (4) | 0.9517 (3) | 0.8860 (2) | 0.1299 (11) | |
H31 | 0.2855 | 0.8788 | 0.8545 | 0.195* | |
N1 | 0.8834 (2) | 0.7313 (2) | 0.79930 (11) | 0.0516 (4) | |
N2 | 0.9601 (2) | 0.4742 (2) | 0.65327 (11) | 0.0501 (4) | |
C11 | 0.8168 (3) | 0.8559 (2) | 0.70050 (16) | 0.0534 (5) | |
C12 | 0.8943 (3) | 0.8336 (3) | 0.63995 (17) | 0.0613 (6) | |
C13 | 0.8847 (4) | 0.8902 (4) | 0.5671 (2) | 0.0792 (9) | |
H13 | 0.9327 | 0.8757 | 0.5264 | 0.095* | |
C14 | 0.8081 (3) | 0.9639 (4) | 0.5556 (2) | 0.0805 (9) | |
H14 | 0.8091 | 1.0023 | 0.5087 | 0.097* | |
C15 | 0.7267 (3) | 0.9840 (3) | 0.61299 (18) | 0.0643 (7) | |
C16 | 0.6392 (3) | 1.0558 (3) | 0.5979 (2) | 0.0742 (8) | |
H16 | 0.6414 | 1.0949 | 0.5512 | 0.089* | |
C17 | 0.5539 (4) | 1.0677 (3) | 0.6500 (2) | 0.0836 (9) | |
H17 | 0.4953 | 1.1118 | 0.6384 | 0.100* | |
C18 | 0.5546 (4) | 1.0138 (3) | 0.7207 (2) | 0.0807 (9) | |
H18 | 0.4962 | 1.0223 | 0.7568 | 0.097* | |
C19 | 0.6398 (3) | 0.9479 (3) | 0.73868 (18) | 0.0672 (7) | |
H19 | 0.6378 | 0.9128 | 0.7869 | 0.081* | |
C110 | 0.7307 (3) | 0.9316 (2) | 0.68617 (16) | 0.0568 (6) | |
C111 | 0.8221 (3) | 0.8072 (3) | 0.77553 (15) | 0.0537 (5) | |
H111 | 0.7751 | 0.8334 | 0.8129 | 0.064* | |
C112 | 0.8725 (3) | 0.6969 (3) | 0.87846 (14) | 0.0533 (5) | |
C113 | 0.8627 (3) | 0.5682 (3) | 0.88848 (14) | 0.0542 (5) | |
C114 | 0.8481 (3) | 0.5276 (3) | 0.96369 (16) | 0.0638 (6) | |
H114 | 0.8392 | 0.4410 | 0.9699 | 0.077* | |
C115 | 0.8465 (3) | 0.6150 (4) | 1.02872 (18) | 0.0785 (9) | |
H115 | 0.8365 | 0.5869 | 1.0789 | 0.094* | |
C116 | 0.8596 (4) | 0.7426 (4) | 1.02103 (17) | 0.0802 (9) | |
H116 | 0.8589 | 0.8010 | 1.0658 | 0.096* | |
C117 | 0.8739 (3) | 0.7852 (3) | 0.94632 (16) | 0.0666 (7) | |
H117 | 0.8845 | 0.8729 | 0.9414 | 0.080* | |
C118 | 0.8186 (4) | 0.3457 (3) | 0.8171 (2) | 0.0725 (7) | |
H1A | 0.8847 | 0.3325 | 0.8581 | 0.109* | |
H1B | 0.8180 | 0.3028 | 0.7636 | 0.109* | |
H1C | 0.7200 | 0.3044 | 0.8276 | 0.109* | |
C21 | 1.1729 (3) | 0.4766 (3) | 0.74245 (15) | 0.0530 (5) | |
C22 | 1.2349 (3) | 0.6136 (3) | 0.78679 (15) | 0.0564 (6) | |
C23 | 1.3735 (3) | 0.6663 (3) | 0.84453 (19) | 0.0702 (7) | |
H23 | 1.4191 | 0.7586 | 0.8712 | 0.084* | |
C24 | 1.4397 (3) | 0.5866 (3) | 0.8614 (2) | 0.0751 (8) | |
H24 | 1.5303 | 0.6255 | 0.8989 | 0.090* | |
C25 | 1.3748 (3) | 0.4444 (3) | 0.82358 (18) | 0.0651 (7) | |
C26 | 1.4392 (4) | 0.3589 (4) | 0.8477 (2) | 0.0842 (9) | |
H26 | 1.5269 | 0.3974 | 0.8876 | 0.101* | |
C27 | 1.3765 (4) | 0.2238 (5) | 0.8144 (3) | 0.0947 (11) | |
H27 | 1.4204 | 0.1691 | 0.8307 | 0.114* | |
C28 | 1.2429 (5) | 0.1650 (4) | 0.7543 (3) | 0.0964 (11) | |
H28 | 1.1992 | 0.0714 | 0.7305 | 0.116* | |
C29 | 1.1774 (4) | 0.2445 (3) | 0.7306 (2) | 0.0782 (8) | |
H29 | 1.0881 | 0.2031 | 0.6919 | 0.094* | |
C210 | 1.2415 (3) | 0.3883 (3) | 0.76334 (17) | 0.0590 (6) | |
C211 | 1.0484 (3) | 0.4218 (3) | 0.67385 (15) | 0.0538 (5) | |
H211 | 1.0293 | 0.3391 | 0.6405 | 0.065* | |
C212 | 0.8515 (3) | 0.4114 (2) | 0.57855 (14) | 0.0516 (5) | |
C213 | 0.7158 (3) | 0.4153 (3) | 0.57614 (15) | 0.0556 (5) | |
C214 | 0.6079 (3) | 0.3604 (3) | 0.50485 (18) | 0.0682 (7) | |
H214 | 0.5171 | 0.3616 | 0.5035 | 0.082* | |
C215 | 0.6361 (3) | 0.3032 (3) | 0.43491 (17) | 0.0725 (8) | |
H215 | 0.5641 | 0.2684 | 0.3863 | 0.087* | |
C216 | 0.7667 (3) | 0.2966 (3) | 0.43559 (16) | 0.0673 (7) | |
H216 | 0.7825 | 0.2561 | 0.3883 | 0.081* | |
C217 | 0.8756 (3) | 0.3510 (3) | 0.50751 (15) | 0.0591 (6) | |
H217 | 0.9651 | 0.3473 | 0.5084 | 0.071* | |
C218 | 0.5632 (4) | 0.4713 (4) | 0.6555 (2) | 0.0815 (9) | |
H2A | 0.5411 | 0.5260 | 0.6199 | 0.122* | |
H2B | 0.5667 | 0.5071 | 0.7114 | 0.122* | |
H2C | 0.4874 | 0.3769 | 0.6396 | 0.122* | |
C31 | 0.2657 (5) | 0.8758 (6) | 1.0085 (4) | 0.143 (2) | |
H31A | 0.2104 | 0.7824 | 0.9778 | 0.214* | |
H31B | 0.2147 | 0.8905 | 1.0498 | 0.214* | |
H31C | 0.3629 | 0.8908 | 1.0345 | 0.214* | |
C32 | 0.2797 (6) | 0.9742 (5) | 0.9519 (3) | 0.1190 (15) | |
H32A | 0.1819 | 0.9647 | 0.9299 | 0.143* | |
H32B | 0.3402 | 1.0682 | 0.9827 | 0.143* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Zn1 | 0.06121 (19) | 0.06208 (19) | 0.05160 (17) | 0.03526 (14) | 0.02026 (12) | 0.01400 (12) |
O11 | 0.0831 (12) | 0.0935 (14) | 0.0735 (12) | 0.0568 (12) | 0.0434 (10) | 0.0418 (11) |
O12 | 0.0906 (13) | 0.0610 (10) | 0.0550 (10) | 0.0363 (10) | 0.0260 (9) | 0.0197 (8) |
O21 | 0.0607 (10) | 0.0575 (10) | 0.0692 (11) | 0.0284 (8) | 0.0115 (8) | 0.0068 (8) |
O22 | 0.0603 (10) | 0.0989 (14) | 0.0541 (10) | 0.0421 (10) | 0.0187 (8) | 0.0118 (9) |
O31 | 0.133 (3) | 0.096 (2) | 0.148 (3) | 0.0442 (19) | 0.034 (2) | 0.0072 (19) |
N1 | 0.0592 (11) | 0.0583 (11) | 0.0472 (10) | 0.0322 (9) | 0.0178 (8) | 0.0168 (8) |
N2 | 0.0480 (10) | 0.0571 (11) | 0.0461 (10) | 0.0231 (9) | 0.0156 (8) | 0.0106 (8) |
C11 | 0.0557 (13) | 0.0498 (12) | 0.0596 (13) | 0.0251 (10) | 0.0171 (10) | 0.0188 (10) |
C12 | 0.0606 (14) | 0.0671 (15) | 0.0679 (15) | 0.0307 (12) | 0.0273 (12) | 0.0336 (13) |
C13 | 0.0793 (19) | 0.101 (2) | 0.083 (2) | 0.0474 (18) | 0.0457 (16) | 0.0532 (18) |
C14 | 0.0718 (17) | 0.094 (2) | 0.088 (2) | 0.0363 (16) | 0.0270 (15) | 0.0569 (18) |
C15 | 0.0598 (14) | 0.0520 (14) | 0.0774 (17) | 0.0195 (11) | 0.0113 (13) | 0.0281 (12) |
C16 | 0.0721 (17) | 0.0578 (15) | 0.087 (2) | 0.0245 (14) | 0.0037 (15) | 0.0305 (14) |
C17 | 0.093 (2) | 0.0668 (18) | 0.104 (3) | 0.0521 (18) | 0.0092 (19) | 0.0143 (17) |
C18 | 0.101 (2) | 0.080 (2) | 0.082 (2) | 0.0615 (19) | 0.0163 (17) | 0.0095 (16) |
C19 | 0.0843 (18) | 0.0646 (16) | 0.0640 (16) | 0.0466 (15) | 0.0122 (13) | 0.0067 (12) |
C110 | 0.0584 (13) | 0.0434 (12) | 0.0631 (14) | 0.0191 (10) | 0.0076 (11) | 0.0129 (10) |
C111 | 0.0572 (13) | 0.0568 (13) | 0.0551 (13) | 0.0306 (11) | 0.0185 (10) | 0.0140 (10) |
C112 | 0.0509 (12) | 0.0729 (15) | 0.0462 (11) | 0.0335 (11) | 0.0178 (9) | 0.0181 (10) |
C113 | 0.0510 (12) | 0.0687 (15) | 0.0495 (12) | 0.0290 (11) | 0.0169 (10) | 0.0218 (11) |
C114 | 0.0594 (14) | 0.0842 (18) | 0.0574 (14) | 0.0350 (13) | 0.0199 (11) | 0.0316 (13) |
C115 | 0.0764 (18) | 0.126 (3) | 0.0524 (15) | 0.0559 (19) | 0.0263 (13) | 0.0346 (16) |
C116 | 0.087 (2) | 0.124 (3) | 0.0463 (14) | 0.062 (2) | 0.0225 (13) | 0.0110 (15) |
C117 | 0.0749 (16) | 0.0851 (19) | 0.0554 (14) | 0.0496 (15) | 0.0180 (12) | 0.0130 (13) |
C118 | 0.0800 (19) | 0.0595 (16) | 0.0789 (19) | 0.0288 (14) | 0.0230 (15) | 0.0221 (14) |
C21 | 0.0507 (12) | 0.0595 (14) | 0.0574 (13) | 0.0291 (11) | 0.0209 (10) | 0.0147 (11) |
C22 | 0.0502 (12) | 0.0626 (14) | 0.0584 (13) | 0.0255 (11) | 0.0192 (10) | 0.0112 (11) |
C23 | 0.0504 (13) | 0.0702 (17) | 0.0800 (19) | 0.0221 (13) | 0.0084 (12) | 0.0066 (14) |
C24 | 0.0468 (13) | 0.091 (2) | 0.0826 (19) | 0.0276 (14) | 0.0115 (13) | 0.0150 (16) |
C25 | 0.0526 (13) | 0.0890 (19) | 0.0732 (16) | 0.0416 (14) | 0.0306 (12) | 0.0288 (14) |
C26 | 0.0708 (18) | 0.117 (3) | 0.100 (2) | 0.066 (2) | 0.0341 (17) | 0.037 (2) |
C27 | 0.094 (2) | 0.117 (3) | 0.120 (3) | 0.080 (2) | 0.040 (2) | 0.044 (2) |
C28 | 0.113 (3) | 0.084 (2) | 0.124 (3) | 0.065 (2) | 0.048 (2) | 0.029 (2) |
C29 | 0.0823 (19) | 0.0753 (19) | 0.091 (2) | 0.0474 (17) | 0.0222 (16) | 0.0155 (16) |
C210 | 0.0568 (13) | 0.0726 (16) | 0.0650 (15) | 0.0390 (12) | 0.0286 (11) | 0.0201 (12) |
C211 | 0.0541 (12) | 0.0557 (13) | 0.0564 (13) | 0.0262 (11) | 0.0225 (10) | 0.0105 (10) |
C212 | 0.0507 (12) | 0.0533 (12) | 0.0477 (11) | 0.0176 (10) | 0.0171 (9) | 0.0146 (10) |
C213 | 0.0573 (13) | 0.0618 (14) | 0.0488 (12) | 0.0246 (11) | 0.0182 (10) | 0.0171 (10) |
C214 | 0.0565 (14) | 0.0785 (18) | 0.0624 (16) | 0.0241 (13) | 0.0096 (12) | 0.0186 (13) |
C215 | 0.0730 (18) | 0.0739 (18) | 0.0481 (14) | 0.0164 (14) | 0.0045 (12) | 0.0085 (12) |
C216 | 0.0711 (17) | 0.0660 (16) | 0.0488 (13) | 0.0150 (13) | 0.0217 (12) | 0.0076 (11) |
C217 | 0.0626 (14) | 0.0562 (14) | 0.0552 (14) | 0.0198 (11) | 0.0254 (11) | 0.0126 (11) |
C218 | 0.0686 (17) | 0.107 (2) | 0.082 (2) | 0.0487 (17) | 0.0283 (15) | 0.0195 (18) |
C31 | 0.096 (3) | 0.167 (5) | 0.161 (5) | 0.046 (3) | 0.025 (3) | 0.076 (4) |
C32 | 0.120 (3) | 0.097 (3) | 0.151 (4) | 0.053 (3) | 0.054 (3) | 0.019 (3) |
Zn1—O11 | 1.9674 (18) | C19—H19 | 0.9300 |
Zn1—O12 | 2.4778 (18) | C214—C215 | 1.387 (4) |
Zn1—O21 | 1.9722 (18) | C214—H214 | 0.9300 |
Zn1—O22 | 2.556 (2) | C114—C115 | 1.368 (4) |
Zn1—N1 | 2.0260 (19) | C114—H114 | 0.9300 |
Zn1—N2 | 2.025 (2) | C116—C115 | 1.364 (5) |
O21—C22 | 1.305 (3) | C116—H116 | 0.9300 |
N2—C211 | 1.288 (3) | C12—C13 | 1.438 (4) |
N2—C212 | 1.420 (3) | C17—C16 | 1.349 (5) |
C210—C25 | 1.412 (4) | C17—C18 | 1.380 (5) |
C210—C29 | 1.416 (4) | C17—H17 | 0.9300 |
C210—C21 | 1.460 (3) | C118—H1A | 0.9600 |
N1—C111 | 1.299 (3) | C118—H1B | 0.9600 |
N1—C112 | 1.423 (3) | C118—H1C | 0.9600 |
O12—C113 | 1.363 (3) | C26—C27 | 1.338 (5) |
O12—C118 | 1.425 (3) | C26—H26 | 0.9300 |
O22—C213 | 1.378 (3) | C23—C24 | 1.342 (4) |
O22—C218 | 1.419 (3) | C23—H23 | 0.9300 |
O11—C12 | 1.285 (3) | C16—H16 | 0.9300 |
C21—C22 | 1.407 (4) | C115—H115 | 0.9300 |
C21—C211 | 1.437 (4) | C218—H2A | 0.9600 |
C212—C217 | 1.397 (3) | C218—H2B | 0.9600 |
C212—C213 | 1.399 (3) | C218—H2C | 0.9600 |
C217—C216 | 1.387 (4) | C27—C28 | 1.411 (6) |
C217—H217 | 0.9300 | C27—H27 | 0.9300 |
C213—C214 | 1.374 (4) | C29—C28 | 1.364 (5) |
C112—C113 | 1.396 (4) | C29—H29 | 0.9300 |
C112—C117 | 1.397 (4) | C24—H24 | 0.9300 |
C211—H211 | 0.9300 | C14—C13 | 1.353 (4) |
C22—C23 | 1.431 (4) | C14—H14 | 0.9300 |
C25—C26 | 1.418 (4) | C13—H13 | 0.9300 |
C25—C24 | 1.420 (4) | C18—H18 | 0.9300 |
C111—C11 | 1.420 (3) | C28—H28 | 0.9300 |
C111—H111 | 0.9300 | C216—C215 | 1.364 (4) |
C15—C110 | 1.411 (4) | C216—H216 | 0.9300 |
C15—C14 | 1.412 (4) | C215—H215 | 0.9300 |
C15—C16 | 1.435 (4) | O31—C32 | 1.410 (5) |
C113—C114 | 1.387 (3) | O31—H31 | 0.8200 |
C117—C116 | 1.387 (4) | C32—C31 | 1.486 (7) |
C117—H117 | 0.9300 | C32—H32A | 0.9700 |
C11—C12 | 1.430 (4) | C32—H32B | 0.9700 |
C11—C110 | 1.459 (3) | C31—H31A | 0.9600 |
C19—C18 | 1.372 (4) | C31—H31B | 0.9600 |
C19—C110 | 1.414 (4) | C31—H31C | 0.9600 |
O11—Zn1—O21 | 109.25 (9) | C117—C116—H116 | 120.0 |
O11—Zn1—N2 | 104.67 (8) | O11—C12—C11 | 125.2 (2) |
O21—Zn1—N2 | 90.74 (8) | O11—C12—C13 | 117.5 (2) |
O11—Zn1—N1 | 91.26 (8) | C11—C12—C13 | 117.3 (2) |
O21—Zn1—N1 | 107.75 (8) | C15—C110—C19 | 116.5 (2) |
N2—Zn1—N1 | 150.26 (8) | C15—C110—C11 | 119.4 (2) |
O11—Zn1—O12 | 155.69 (8) | C19—C110—C11 | 123.9 (2) |
O21—Zn1—O12 | 92.20 (7) | C16—C17—C18 | 119.3 (3) |
N2—Zn1—O12 | 85.80 (7) | C16—C17—H17 | 120.3 |
N1—Zn1—O12 | 70.78 (7) | C18—C17—H17 | 120.3 |
C22—O21—Zn1 | 125.37 (16) | O12—C118—H1A | 109.5 |
C211—N2—C212 | 119.0 (2) | O12—C118—H1B | 109.5 |
C211—N2—Zn1 | 122.62 (17) | H1A—C118—H1B | 109.5 |
C212—N2—Zn1 | 118.39 (16) | O12—C118—H1C | 109.5 |
C25—C210—C29 | 116.5 (3) | H1A—C118—H1C | 109.5 |
C25—C210—C21 | 119.5 (2) | H1B—C118—H1C | 109.5 |
C29—C210—C21 | 123.9 (3) | C27—C26—C25 | 121.4 (3) |
C111—N1—C112 | 117.8 (2) | C27—C26—H26 | 119.3 |
C111—N1—Zn1 | 122.20 (16) | C25—C26—H26 | 119.3 |
C112—N1—Zn1 | 119.62 (15) | C24—C23—C22 | 122.1 (3) |
C113—O12—C118 | 118.9 (2) | C24—C23—H23 | 119.0 |
C113—O12—Zn1 | 108.46 (14) | C22—C23—H23 | 119.0 |
C118—O12—Zn1 | 132.64 (17) | C17—C16—C15 | 121.4 (3) |
C213—O22—C218 | 118.5 (2) | C17—C16—H16 | 119.3 |
C12—O11—Zn1 | 127.09 (16) | C15—C16—H16 | 119.3 |
C22—C21—C211 | 122.4 (2) | C116—C115—C114 | 121.0 (3) |
C22—C21—C210 | 119.4 (2) | C116—C115—H115 | 119.5 |
C211—C21—C210 | 118.1 (2) | C114—C115—H115 | 119.5 |
C217—C212—C213 | 119.0 (2) | O22—C218—H2A | 109.5 |
C217—C212—N2 | 123.3 (2) | O22—C218—H2B | 109.5 |
C213—C212—N2 | 117.6 (2) | H2A—C218—H2B | 109.5 |
C216—C217—C212 | 120.3 (3) | O22—C218—H2C | 109.5 |
C216—C217—H217 | 119.9 | H2A—C218—H2C | 109.5 |
C212—C217—H217 | 119.9 | H2B—C218—H2C | 109.5 |
C214—C213—O22 | 125.0 (2) | C26—C27—C28 | 119.3 (3) |
C214—C213—C212 | 120.4 (2) | C26—C27—H27 | 120.3 |
O22—C213—C212 | 114.6 (2) | C28—C27—H27 | 120.3 |
C113—C112—C117 | 118.7 (2) | C28—C29—C210 | 121.9 (3) |
C113—C112—N1 | 117.5 (2) | C28—C29—H29 | 119.1 |
C117—C112—N1 | 123.8 (2) | C210—C29—H29 | 119.1 |
N2—C211—C21 | 127.3 (2) | C23—C24—C25 | 121.6 (3) |
N2—C211—H211 | 116.3 | C23—C24—H24 | 119.2 |
C21—C211—H211 | 116.3 | C25—C24—H24 | 119.2 |
O21—C22—C21 | 124.8 (2) | C13—C14—C15 | 121.8 (3) |
O21—C22—C23 | 116.9 (2) | C13—C14—H14 | 119.1 |
C21—C22—C23 | 118.2 (2) | C15—C14—H14 | 119.1 |
C210—C25—C26 | 120.4 (3) | C14—C13—C12 | 122.2 (3) |
C210—C25—C24 | 118.8 (2) | C14—C13—H13 | 118.9 |
C26—C25—C24 | 120.8 (3) | C12—C13—H13 | 118.9 |
N1—C111—C11 | 129.1 (2) | C19—C18—C17 | 121.2 (3) |
N1—C111—H111 | 115.4 | C19—C18—H18 | 119.4 |
C11—C111—H111 | 115.4 | C17—C18—H18 | 119.4 |
C110—C15—C14 | 119.3 (2) | C29—C28—C27 | 120.5 (4) |
C110—C15—C16 | 119.5 (3) | C29—C28—H28 | 119.7 |
C14—C15—C16 | 121.2 (3) | C27—C28—H28 | 119.7 |
O12—C113—C114 | 124.8 (2) | C215—C216—C217 | 119.3 (3) |
O12—C113—C112 | 115.2 (2) | C215—C216—H216 | 120.3 |
C114—C113—C112 | 120.0 (2) | C217—C216—H216 | 120.3 |
C116—C117—C112 | 120.2 (3) | C216—C215—C214 | 121.7 (3) |
C116—C117—H117 | 119.9 | C216—C215—H215 | 119.2 |
C112—C117—H117 | 119.9 | C214—C215—H215 | 119.2 |
C111—C11—C12 | 121.8 (2) | C32—O31—H31 | 109.5 |
C111—C11—C110 | 118.3 (2) | O31—C32—C31 | 112.5 (4) |
C12—C11—C110 | 119.9 (2) | O31—C32—H32A | 109.1 |
C18—C19—C110 | 122.0 (3) | C31—C32—H32A | 109.1 |
C18—C19—H19 | 119.0 | O31—C32—H32B | 109.1 |
C110—C19—H19 | 119.0 | C31—C32—H32B | 109.1 |
C213—C214—C215 | 119.3 (3) | H32A—C32—H32B | 107.8 |
C213—C214—H214 | 120.4 | C32—C31—H31A | 109.5 |
C215—C214—H214 | 120.4 | C32—C31—H31B | 109.5 |
C115—C114—C113 | 120.1 (3) | H31A—C31—H31B | 109.5 |
C115—C114—H114 | 120.0 | C32—C31—H31C | 109.5 |
C113—C114—H114 | 120.0 | H31A—C31—H31C | 109.5 |
C115—C116—C117 | 120.0 (3) | H31B—C31—H31C | 109.5 |
C115—C116—H116 | 120.0 |
D—H···A | D—H | H···A | D···A | D—H···A |
O31—H31···O21i | 0.82 | 1.97 | 2.781 (4) | 169 |
C23—H23···O31ii | 0.93 | 2.53 | 3.263 (6) | 136 |
C27—H27···O31iii | 0.93 | 2.48 | 3.225 (6) | 137 |
Symmetry codes: (i) x−1, y, z; (ii) x+1, y, z; (iii) x+1, y−1, z. |
Experimental details
Crystal data | |
Chemical formula | [Zn(C18H14NO2)2]·C2H6O |
Mr | 664.06 |
Crystal system, space group | Triclinic, P1 |
Temperature (K) | 295 |
a, b, c (Å) | 10.2078 (15), 10.9122 (14), 16.7214 (10) |
α, β, γ (°) | 96.550 (16), 98.113 (8), 115.592 (12) |
V (Å3) | 1630.8 (4) |
Z | 2 |
Radiation type | Mo Kα |
µ (mm−1) | 0.80 |
Crystal size (mm) | 0.58 × 0.11 × 0.09 |
Data collection | |
Diffractometer | Philips PW1100 upgraded by Stoe diffractometer |
Absorption correction | ψ scan X-RED (Stoe & Cie, 1995) |
Tmin, Tmax | 0.90, 0.93 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 9774, 9462, 5673 |
Rint | 0.091 |
(sin θ/λ)max (Å−1) | 0.703 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.056, 0.165, 1.03 |
No. of reflections | 9462 |
No. of parameters | 419 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.69, −0.63 |
Computer programs: STADI4 (Stoe & Cie, 1995), STADI4, X-RED (Stoe & Cie, 1995), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), PLATON (Spek, 2003), SHELXL97.
Zn1—O11 | 1.9674 (18) | N2—C212 | 1.420 (3) |
Zn1—O12 | 2.4778 (18) | N1—C111 | 1.299 (3) |
Zn1—O21 | 1.9722 (18) | N1—C112 | 1.423 (3) |
Zn1—O22 | 2.556 (2) | O12—C113 | 1.363 (3) |
Zn1—N1 | 2.0260 (19) | O22—C213 | 1.378 (3) |
Zn1—N2 | 2.025 (2) | O11—C12 | 1.285 (3) |
O21—C22 | 1.305 (3) | C23—C24 | 1.342 (4) |
N2—C211 | 1.288 (3) | C14—C13 | 1.353 (4) |
O11—Zn1—O21 | 109.25 (9) | N2—Zn1—N1 | 150.26 (8) |
O11—Zn1—N2 | 104.67 (8) | O11—Zn1—O12 | 155.69 (8) |
O21—Zn1—N2 | 90.74 (8) | O21—Zn1—O12 | 92.20 (7) |
O11—Zn1—N1 | 91.26 (8) | N2—Zn1—O12 | 85.80 (7) |
O21—Zn1—N1 | 107.75 (8) | N1—Zn1—O12 | 70.78 (7) |
D—H···A | D—H | H···A | D···A | D—H···A |
O31—H31···O21i | 0.82 | 1.97 | 2.781 (4) | 169 |
C23—H23···O31ii | 0.93 | 2.53 | 3.263 (6) | 136 |
C27—H27···O31iii | 0.93 | 2.48 | 3.225 (6) | 137 |
Symmetry codes: (i) x−1, y, z; (ii) x+1, y, z; (iii) x+1, y−1, z. |
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Schiff-bases derived from 2-hydroxy-1-naphthaldehyde are interesting ligands with excellent donor abilities. Such derivatives having N, O or other heteroatom donors are good chelating agents (Elerman et al., 1992; Elmali et al., 1993; Bashirpoor et al., 1997; Cindrić et al., 2004; Popović, Roje, Pavlović, Matković-Čalogović & Giester, 2001; Popović, Roje, Pavlović, Matković-Čalogović, Rajić & Giester, 2001; Popović et al., 2004).
In the crystal structure of the title compound, (I), the Zn atom displays a highly distorted octahedral coordination involving four O and two N atoms of two molecules of the Schiff base acting as a tridentate ligand (Fig. 1). Coordination of the ZnII ion by the two methoxy O atoms is weakened, which is reflected in the lengthening of the Zn—O(methoxy) distances [2.4778 (18) and 2.556 (2) Å] in comparison with the Zn—O(oxo) bond lengths [1.9674 (18) and 1.9722 (18) Å]. In a previously reported structure (Shol'nikova et al., 1970), the Zn—O bond distances were also found in a wide range (1.965–2.406 Å). The Zn—N [2.025 (2) and 2.0260 (19) Å] distances in (I) are comparable with the corresponding values reported in the literature (Mukherjee et al., 2000; Rajsekhar et al., 2003).
Delocalization of the π electrons accounts for the O11—C12, O21—C22, N1—C111 and N2—C211 bond lengths [1.285 (3), 1.305 (3), 1.299 (3) and 1.288 (3) Å, respectively] being intermediate between single- and double-bond values (Allen et al., 1987). Bond lengths in the naphthalene moieties are mostly as expected; shortening of the C13—C14 and C23—-C24 bonds [1.353 (4) and 1.342 (4) Å] is consistent with the quinoid effect (Exelby & Grinter, 1965).
The six-membered chelate rings, Zn1/O11/C12/C11/C111/N1 and Zn1/O21/C22/C21/C211/N2, are almost planar. The angles between the planes of the naphthalene rings and the phenyl rings of the N-substituents [40.11 (8) and 53.55 (8)°] indicate non-planarity of the Schiff base ligands.
In addition to van der Waals interactions, the crystal packing in (I) is stabilized by weak intermolecular C—H···O hydrogen bonds. The ethanol solvent molecule is linked to the methoxy group of one ligand molecule by an O—H···O hydrogen bond (Table 2).