Abstract
C19H20O4, monoclinic, P21/c (no. 14), a = 16.5979(5) Å, b = 8.5654(2) Å, c = 11.8418(4) Å, β = 108.537(4)°, V = 1596.18(8) Å3, Z = 4, Rgt(F) = 0.0385, wRref(F2) = 0.0973, T = 190 K.
The crystal structure is shown in the figure. Tables 1–3 contain details of the measurement method and a list of the atoms including atomic coordinates and displacement parameters.
Data collection and handling.
| Crystal: | Colourless, prism, size 0.24×0.35×0.55 mm |
| Wavelength: | Mo Kα radiation (0.7107 Å) |
| μ: | 0.90 cm−1 |
| Diffractometer, scan mode: | Xcalibur, Sapphire3, ω scans |
| 2θmax: | 53.98° |
| N(hkl)measured, N(hkl)unique: | 11694, 3426 |
| Criterion for Iobs, N(hkl)gt: | Iobs > 2 σ(Iobs), 3015 |
| N(param)refined: | 208 |
| Programs: | CrysAlisPRO [11], SIR2004 [12], SHELX [13], ORTEP [14] |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2).
| Atom | Site | x | y | z | Uiso |
|---|---|---|---|---|---|
| H(1) | 4e | 0.5044 | −0.2759 | 0.9176 | 0.043 |
| H(4) | 4e | 0.7171 | 0.0536 | 1.1474 | 0.040 |
| H(5) | 4e | 0.6750 | 0.1104 | 1.3131 | 0.045 |
| H(6) | 4e | 0.5526 | 0.0000 | 1.3355 | 0.046 |
| H(7) | 4e | 0.4715 | −0.1706 | 1.1912 | 0.040 |
| H(8A) | 4e | 0.7543 | −0.0531 | 0.9909 | 0.038 |
| H(8B) | 4e | 0.6827 | 0.0766 | 0.9343 | 0.038 |
| H(9B) | 4e | 0.6338 | −0.0770 | 0.7565 | 0.038 |
| H(9A) | 4e | 0.7091 | −0.1986 | 0.8128 | 0.038 |
| H(10A) | 4e | 0.8103 | 0.0018 | 0.8152 | 0.036 |
| H(10B) | 4e | 0.7336 | 0.1186 | 0.7533 | 0.036 |
| H(11A) | 4e | 0.7744 | −0.1580 | 0.6467 | 0.036 |
| H(11B) | 4e | 0.6893 | −0.0608 | 0.5864 | 0.036 |
| H(12A) | 4e | 0.7867 | 0.0133 | 0.4935 | 0.037 |
| H(12B) | 4e | 0.7757 | 0.1594 | 0.5723 | 0.037 |
| H(14) | 4e | 0.8562 | 0.2378 | 0.4589 | 0.038 |
| H(15) | 4e | 0.9583 | 0.3629 | 0.3944 | 0.043 |
| H(16) | 4e | 1.1030 | 0.3248 | 0.4922 | 0.046 |
| H(17) | 4e | 1.1458 | 0.1578 | 0.6552 | 0.041 |
| H(19) | 4e | 1.0138 | −0.0749 | 0.7751 | 0.038 |
Atomic coordinates and displacement parameters (Å2).
| Atom | Site | x | y | z | U11 | U22 | U33 | U12 | U13 | U23 |
|---|---|---|---|---|---|---|---|---|---|---|
| C(1) | 4e | 0.48905(8) | −0.2603(2) | 0.9875(1) | 0.0363(7) | 0.0393(7) | 0.0314(6) | −0.0025(6) | 0.0093(5) | 0.0052(5) |
| C(2) | 4e | 0.54368(7) | −0.1590(1) | 1.0809(1) | 0.0277(6) | 0.0287(6) | 0.0262(6) | 0.0050(5) | 0.0078(5) | 0.0061(5) |
| C(3) | 4e | 0.61737(7) | −0.0909(1) | 1.0679(1) | 0.0286(6) | 0.0289(6) | 0.0257(6) | 0.0069(5) | 0.0097(5) | 0.0043(5) |
| C(4) | 4e | 0.66675(8) | 0.0086(2) | 1.1551(1) | 0.0307(6) | 0.0340(7) | 0.0331(6) | 0.0012(5) | 0.0086(5) | 0.0022(5) |
| C(5) | 4e | 0.64160(9) | 0.0414(2) | 1.2537(1) | 0.0450(7) | 0.0348(7) | 0.0293(6) | 0.0014(6) | 0.0068(6) | −0.0019(5) |
| C(6) | 4e | 0.56898(9) | −0.0240(2) | 1.2676(1) | 0.0504(8) | 0.0375(7) | 0.0308(6) | 0.0078(6) | 0.0193(6) | 0.0022(5) |
| C(7) | 4e | 0.52092(8) | −0.1243(2) | 1.1817(1) | 0.0343(6) | 0.0350(7) | 0.0334(6) | 0.0063(5) | 0.0160(5) | 0.0081(5) |
| C(8) | 4e | 0.69667(7) | −0.0358(2) | 0.9340(1) | 0.0251(6) | 0.0385(7) | 0.0341(6) | −0.0035(5) | 0.0127(5) | −0.0012(5) |
| C(9) | 4e | 0.69297(8) | −0.0870(2) | 0.8104(1) | 0.0278(6) | 0.0374(7) | 0.0342(6) | −0.0041(5) | 0.0145(5) | −0.0032(5) |
| C(10) | 4e | 0.75139(7) | 0.0077(2) | 0.7599(1) | 0.0272(6) | 0.0331(6) | 0.0323(6) | −0.0028(5) | 0.0128(5) | −0.0016(5) |
| C(11) | 4e | 0.74929(7) | −0.0520(2) | 0.6376(1) | 0.0240(5) | 0.0360(7) | 0.0301(6) | −0.0030(5) | 0.0088(5) | −0.0020(5) |
| C(12) | 4e | 0.79639(7) | 0.0505(2) | 0.5759(1) | 0.0240(6) | 0.0389(7) | 0.0285(6) | 0.0010(5) | 0.0074(5) | 0.0032(5) |
| C(13) | 4e | 0.94026(7) | 0.1208(1) | 0.5971(1) | 0.0295(6) | 0.0246(6) | 0.0276(6) | −0.0025(4) | 0.0142(5) | −0.0037(4) |
| C(14) | 4e | 0.91493(8) | 0.2207(2) | 0.4993(1) | 0.0350(6) | 0.0300(6) | 0.0319(6) | 0.0016(5) | 0.0140(5) | 0.0020(5) |
| C(15) | 4e | 0.97581(9) | 0.2951(2) | 0.4613(1) | 0.0495(8) | 0.0268(6) | 0.0377(7) | −0.0014(6) | 0.0220(6) | 0.0027(5) |
| C(16) | 4e | 1.06192(9) | 0.2726(2) | 0.5189(1) | 0.0445(7) | 0.0325(7) | 0.0460(8) | −0.0117(6) | 0.0264(6) | −0.0038(6) |
| C(17) | 4e | 1.08691(8) | 0.1735(2) | 0.6153(1) | 0.0316(6) | 0.0347(7) | 0.0388(7) | −0.0077(5) | 0.0159(5) | −0.0082(5) |
| C(18) | 4e | 1.02717(7) | 0.0957(1) | 0.6555(1) | 0.0292(6) | 0.0278(6) | 0.0283(6) | −0.0036(5) | 0.0128(5) | −0.0066(5) |
| C(19) | 4e | 1.05571(8) | −0.0162(2) | 0.7546(1) | 0.0261(6) | 0.0405(7) | 0.0292(6) | −0.0007(5) | 0.0102(5) | −0.0019(5) |
| O(1) | 4e | 0.42585(6) | −0.3254(1) | 0.99384(9) | 0.0456(6) | 0.0572(7) | 0.0436(6) | −0.0181(5) | 0.0074(5) | 0.0101(5) |
| O(2) | 4e | 0.63525(5) | −0.1284(1) | 0.96666(7) | 0.0345(5) | 0.0376(5) | 0.0328(5) | −0.0047(4) | 0.0181(4) | −0.0035(4) |
| O(3) | 4e | 0.88550(5) | 0.0441(1) | 0.64226(7) | 0.0231(4) | 0.0378(5) | 0.0288(4) | −0.0008(3) | 0.0100(3) | 0.0061(4) |
| O(4) | 4e | 1.12945(6) | −0.0376(2) | 0.81153(9) | 0.0278(5) | 0.0810(8) | 0.0451(6) | 0.0002(5) | 0.0055(4) | 0.0158(5) |
Source of material
Salicylaldehyde (0.1 mol) and K2CO3 (0.1 mol) were mixed in DMF and heated to boiling temperature. 0.05 mol of 1,5-dibromopentane dissolved in DMF were then added and the reaction mixture was refluxed for 4 h. After the reaction was complete, 500 mL of water were added and the resulting percipitate was filtered and washed with water. The product was recrystallized from absolute ethanol. Single crystals suitable for diffraction experiments were obtained by slow evaporation of an ethanol solution.
Experimental details
All H atoms were positioned geometrically and refined using a riding model with C—H = 0.93–0.97 Å and with Uiso(H) = 1.2 times Ueq(C).
Discussion
Aldehydes comprising two carbonyl functional groups (so called two-arm aldehydes) are promising starting materials for synthesis of macrocyclic Schiff bases. Condensation reactions of ortho substituted dialdehydes with primary amines and ketones have been recently investigated for preparation of complex macrocyclic compounds [1, 2], porous organic materials [3] and macrocyclic chalcones [4]. The title molecule is comprised of two formylphenoxy groups linked by five methylene carbon atoms (see the figure). The benzaldehyde groups enclose a dihedral angle of 67.5(6)° and therefore the molecule is non-planar. It is interesting to note, as reported in our previous contributions [5, 6], as well as in other related studies [7–9], that similar dialdehydes with even number of atoms in the aliphatic chain are planar, while molecules with odd number of atoms are non-planar. These deviations cause differences in some properties of these dialdehydes, such as melting point and crystal packing arrangement. In the crystal, the molecules are linked into dimers through weak C—H⋯O hydrogen bonds [graph set R22(28)] [10]. These dimers are connected into chains along [101] direction via weak C—H⋯O interactions. Additional stabilization of the crystal structure is achieved by a number of weak C—H⋯O and C—H⋯π interactions which are linking the chains of dimers.
Acknowledgements:
The authors wish to thank prof. Dubravka Matković-Čalogović for all the help during data collection and structure refinement.
References
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©2016 Tomislav Balić et al., published by De Gruyter.
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