organic compounds
[(E)-1-(Naphthalen-2-yl)ethylidene](naphthalen-1-ylmethyl)amine
aDepartment of Chemistry, University of Aveiro, CICECO, 3810-193, Aveiro, Portugal
*Correspondence e-mail: filipe.paz@ua.pt
The title compound, C23H19N, was obtained unexpectedly from the reaction of [Eu(nta)3(PzPy)] {Hnta = 1-(2-naphthoyl)-3,3,3-trifluoroacetone and PzPy = 2-[3(5)-pyrazolyl]pyridine} with 1-naphthylmethylamine. The 1- and 2-naphthyl groups are essentially planar [r.m.s. deviations of 0.007 and 0.011 Å, respectively] and subtend angles of 38.69 (11) and 16.50 (11)°, respectively, with the central CH3—C=N—CH2 unit, which is also almost planar [r.m.s. deviation = 0.002 Å]. In the crystal, the molecules are disposed in zigzag-type fashion, forming layers perpendicular to [100]. Weak supramolecular C—H⋯π interactions contribute to the packing forces.
Related literature
For general background to aldimidines and et al. (1954); Hampe et al. (2004) and references cited therein; Kumar et al. (2008). For general background to β-diketonates, see: Bruno et al. (2008). Filyakova et al. (1996).
see: NortonExperimental
Crystal data
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Refinement
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Data collection: APEX2 (Bruker, 2006); cell SAINT-Plus (Bruker, 2005); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL; molecular graphics: DIAMOND (Brandenburg, 2009); software used to prepare material for publication: SHELXTL.
Supporting information
10.1107/S1600536812041414/nr2032sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536812041414/nr2032Isup2.hkl
Supporting information file. DOI: 10.1107/S1600536812041414/nr2032Isup3.cdx
Supporting information file. DOI: 10.1107/S1600536812041414/nr2032Isup4.cml
All chemicals were purchased from Sigma-Aldrich and used as received. Literature procedures were used to prepare [Eu(nta)3(PzPy)] {with Hnta=1-(2-naphthoyl)-3,3,3-trifluoroacetone and PzPy = 2-[3(5)-pyrazolyl]pyridine} (Bruno et al., 2008).
[Eu(nta)3(PzPy)] (1.00 g, 0.92 mmol) was dissolved in toluene (45 ml) at ambient temperature. 1-Naphthylmethylamine (0.78 ml, 5.5 mmol) was added leading to the formation of an orange solution, which was refluxed for 3 days. The water formed in the reaction was removed by using a Dean-Stark apparatus. The reaction mixture was filtered off and the solvent removed by evaporation under vacuum, leading to the isolation of an orange oil. Suitable crystals of the title compound were isolated by slow cooling of a concentrated solution in diethyl ether.
Selected FT—IR (KBr, cm-1): ν = 3060m, 3049m, 1630 s, 1620m, 1595 s, 1508m, 1503s h, 1370m, 1357m, 1321m, 1287m, 1263m, 1193m, 1127m, 1080m, 1074m, 950m, 945s h, 897m, 864m, 829 s, 796vs, 771 s, 746 s, 734 s, 535m, 524m, 473 s, 405m.
1H NMR (300 MHz, CDCl3, 25 °C): δ = 8.25–7.47 (m, 14H, H-naphthyl), 5.24 (s, 2H, CH2), 2.53 (s, 3H, CH3).
Hydrogen atoms bound to carbon were placed at their idealized positions with C—H = 0.93 Å (aromatic and delocalized), 0.97 Å (—CH2—) and 0.96 Å (terminal —CH3). These hydrogen atoms were included in the final structural model in riding-motion approximation, with the isotropic thermal displacement parameters fixed at 1.2×Ueq (for —CH and the —CH2— moieties) or 1.5× Ueq (for the —CH3 group) of the carbon atom to which they are attached.
Data collection: APEX2 (Bruker, 2006); cell
SAINT-Plus (Bruker, 2005); data reduction: SAINT-Plus (Bruker, 2005); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: DIAMOND (Brandenburg, 2009); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).C23H19N | Z = 2 |
Mr = 309.39 | F(000) = 328 |
Triclinic, P1 | Dx = 1.221 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 6.6304 (5) Å | Cell parameters from 4208 reflections |
b = 7.7772 (5) Å | θ = 2.5–24.2° |
c = 16.7587 (9) Å | µ = 0.07 mm−1 |
α = 77.655 (3)° | T = 296 K |
β = 87.969 (2)° | Block, yellow |
γ = 85.734 (3)° | 0.17 × 0.07 × 0.04 mm |
V = 841.69 (9) Å3 |
Bruker X8 Kappa APEXII CCD diffractometer | 2986 independent reflections |
Radiation source: fine-focus sealed tube | 2021 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.045 |
ω / ϕ scans | θmax = 25.2°, θmin = 3.7° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1998) | h = −7→7 |
Tmin = 0.988, Tmax = 0.997 | k = −9→9 |
14750 measured reflections | l = −19→20 |
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)] = 0.044 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.121 | H-atom parameters constrained |
S = 1.02 | w = 1/[σ2(Fo2) + (0.0562P)2 + 0.1131P] where P = (Fo2 + 2Fc2)/3 |
2986 reflections | (Δ/σ)max < 0.001 |
218 parameters | Δρmax = 0.13 e Å−3 |
0 restraints | Δρmin = −0.16 e Å−3 |
C23H19N | γ = 85.734 (3)° |
Mr = 309.39 | V = 841.69 (9) Å3 |
Triclinic, P1 | Z = 2 |
a = 6.6304 (5) Å | Mo Kα radiation |
b = 7.7772 (5) Å | µ = 0.07 mm−1 |
c = 16.7587 (9) Å | T = 296 K |
α = 77.655 (3)° | 0.17 × 0.07 × 0.04 mm |
β = 87.969 (2)° |
Bruker X8 Kappa APEXII CCD diffractometer | 2986 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 1998) | 2021 reflections with I > 2σ(I) |
Tmin = 0.988, Tmax = 0.997 | Rint = 0.045 |
14750 measured reflections |
R[F2 > 2σ(F2)] = 0.044 | 0 restraints |
wR(F2) = 0.121 | H-atom parameters constrained |
S = 1.02 | Δρmax = 0.13 e Å−3 |
2986 reflections | Δρmin = −0.16 e Å−3 |
218 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 | ||
N1 | 0.1658 (2) | 0.2127 (2) | 0.47556 (8) | 0.0604 (4) | |
C1 | −0.1836 (3) | 0.2591 (3) | 0.52396 (10) | 0.0730 (6) | |
H1A | −0.2092 | 0.3849 | 0.5091 | 0.109* | |
H1B | −0.2531 | 0.2145 | 0.5745 | 0.109* | |
H1C | −0.2313 | 0.2066 | 0.4819 | 0.109* | |
C2 | 0.0396 (2) | 0.2145 (2) | 0.53387 (9) | 0.0486 (4) | |
C3 | 0.1216 (2) | 0.16403 (19) | 0.61818 (9) | 0.0452 (4) | |
C4 | 0.3175 (2) | 0.0775 (2) | 0.63052 (9) | 0.0531 (4) | |
H4 | 0.3918 | 0.0519 | 0.5859 | 0.064* | |
C5 | 0.3988 (3) | 0.0313 (2) | 0.70559 (10) | 0.0576 (4) | |
H5 | 0.5274 | −0.0258 | 0.7115 | 0.069* | |
C6 | 0.2923 (2) | 0.0681 (2) | 0.77506 (9) | 0.0517 (4) | |
C7 | 0.0964 (2) | 0.1538 (2) | 0.76454 (9) | 0.0475 (4) | |
C8 | 0.0156 (2) | 0.1991 (2) | 0.68525 (9) | 0.0485 (4) | |
H8 | −0.1138 | 0.2544 | 0.6784 | 0.058* | |
C9 | −0.0116 (3) | 0.1929 (2) | 0.83342 (10) | 0.0598 (5) | |
H9 | −0.1410 | 0.2484 | 0.8273 | 0.072* | |
C10 | 0.0725 (3) | 0.1499 (3) | 0.90866 (10) | 0.0707 (5) | |
H10 | 0.0004 | 0.1774 | 0.9534 | 0.085* | |
C11 | 0.2652 (3) | 0.0652 (3) | 0.91923 (11) | 0.0745 (6) | |
H11 | 0.3207 | 0.0363 | 0.9710 | 0.089* | |
C12 | 0.3726 (3) | 0.0245 (2) | 0.85451 (10) | 0.0676 (5) | |
H12 | 0.5007 | −0.0328 | 0.8625 | 0.081* | |
C13 | 0.0991 (3) | 0.2558 (3) | 0.39124 (9) | 0.0681 (5) | |
H13A | −0.0210 | 0.3363 | 0.3872 | 0.082* | |
H13B | 0.0631 | 0.1490 | 0.3757 | 0.082* | |
C14 | 0.2595 (2) | 0.33899 (19) | 0.33304 (9) | 0.0454 (4) | |
C15 | 0.4228 (2) | 0.4037 (2) | 0.36071 (9) | 0.0514 (4) | |
H15 | 0.4369 | 0.3926 | 0.4166 | 0.062* | |
C16 | 0.5702 (3) | 0.4866 (2) | 0.30687 (11) | 0.0628 (5) | |
H16 | 0.6787 | 0.5318 | 0.3273 | 0.075* | |
C17 | 0.5556 (3) | 0.5013 (2) | 0.22524 (11) | 0.0633 (5) | |
H17 | 0.6555 | 0.5546 | 0.1902 | 0.076* | |
C18 | 0.3907 (2) | 0.4366 (2) | 0.19305 (9) | 0.0511 (4) | |
C19 | 0.2387 (2) | 0.35522 (19) | 0.24721 (9) | 0.0454 (4) | |
C20 | 0.0741 (3) | 0.2932 (2) | 0.21271 (10) | 0.0593 (5) | |
H20 | −0.0269 | 0.2393 | 0.2469 | 0.071* | |
C21 | 0.0605 (3) | 0.3109 (3) | 0.13055 (10) | 0.0720 (5) | |
H21 | −0.0491 | 0.2689 | 0.1094 | 0.086* | |
C22 | 0.2096 (3) | 0.3916 (3) | 0.07773 (11) | 0.0748 (6) | |
H22 | 0.1989 | 0.4034 | 0.0216 | 0.090* | |
C23 | 0.3697 (3) | 0.4527 (3) | 0.10818 (10) | 0.0678 (5) | |
H23 | 0.4680 | 0.5065 | 0.0724 | 0.081* |
U11 | U22 | U33 | U12 | U13 | U23 | |
N1 | 0.0528 (9) | 0.0836 (11) | 0.0417 (8) | −0.0104 (7) | −0.0017 (6) | −0.0044 (7) |
C1 | 0.0554 (11) | 0.1075 (16) | 0.0545 (11) | 0.0058 (10) | −0.0066 (8) | −0.0166 (10) |
C2 | 0.0478 (10) | 0.0500 (10) | 0.0481 (9) | −0.0084 (7) | −0.0025 (8) | −0.0088 (7) |
C3 | 0.0459 (9) | 0.0443 (9) | 0.0449 (9) | −0.0070 (7) | −0.0010 (7) | −0.0068 (7) |
C4 | 0.0509 (10) | 0.0581 (10) | 0.0507 (9) | −0.0014 (8) | 0.0007 (7) | −0.0136 (8) |
C5 | 0.0497 (10) | 0.0610 (11) | 0.0597 (10) | 0.0067 (8) | −0.0062 (8) | −0.0100 (8) |
C6 | 0.0569 (10) | 0.0467 (10) | 0.0496 (9) | −0.0038 (8) | −0.0056 (7) | −0.0055 (7) |
C7 | 0.0531 (10) | 0.0432 (9) | 0.0451 (9) | −0.0073 (7) | 0.0016 (7) | −0.0064 (7) |
C8 | 0.0465 (9) | 0.0457 (9) | 0.0515 (9) | −0.0023 (7) | −0.0013 (7) | −0.0066 (7) |
C9 | 0.0669 (11) | 0.0587 (11) | 0.0517 (10) | −0.0020 (9) | 0.0057 (8) | −0.0090 (8) |
C10 | 0.0923 (16) | 0.0727 (13) | 0.0460 (10) | −0.0090 (11) | 0.0060 (10) | −0.0103 (9) |
C11 | 0.0926 (15) | 0.0816 (14) | 0.0464 (10) | −0.0087 (12) | −0.0118 (10) | −0.0041 (9) |
C12 | 0.0712 (12) | 0.0705 (12) | 0.0564 (11) | 0.0004 (10) | −0.0162 (9) | −0.0028 (9) |
C13 | 0.0558 (11) | 0.1003 (15) | 0.0451 (10) | −0.0165 (10) | −0.0020 (8) | −0.0045 (9) |
C14 | 0.0476 (9) | 0.0443 (9) | 0.0435 (8) | −0.0005 (7) | −0.0019 (7) | −0.0085 (7) |
C15 | 0.0540 (10) | 0.0530 (10) | 0.0471 (9) | −0.0033 (8) | −0.0077 (7) | −0.0094 (7) |
C16 | 0.0566 (11) | 0.0646 (11) | 0.0666 (11) | −0.0172 (9) | −0.0092 (9) | −0.0071 (9) |
C17 | 0.0558 (11) | 0.0669 (12) | 0.0630 (11) | −0.0149 (9) | 0.0056 (8) | −0.0021 (9) |
C18 | 0.0563 (10) | 0.0468 (9) | 0.0482 (9) | 0.0004 (8) | 0.0031 (7) | −0.0076 (7) |
C19 | 0.0500 (9) | 0.0403 (8) | 0.0456 (8) | 0.0002 (7) | −0.0024 (7) | −0.0095 (7) |
C20 | 0.0633 (11) | 0.0650 (11) | 0.0511 (10) | −0.0145 (9) | −0.0032 (8) | −0.0122 (8) |
C21 | 0.0822 (14) | 0.0832 (14) | 0.0562 (11) | −0.0186 (11) | −0.0112 (10) | −0.0208 (10) |
C22 | 0.0948 (15) | 0.0873 (14) | 0.0448 (10) | −0.0080 (12) | −0.0032 (10) | −0.0187 (9) |
C23 | 0.0776 (13) | 0.0777 (13) | 0.0465 (10) | −0.0068 (10) | 0.0106 (9) | −0.0107 (9) |
N1—C2 | 1.2650 (19) | C11—H11 | 0.9300 |
N1—C13 | 1.4575 (19) | C12—H12 | 0.9300 |
C1—C2 | 1.502 (2) | C13—C14 | 1.504 (2) |
C1—H1A | 0.9600 | C13—H13A | 0.9700 |
C1—H1B | 0.9600 | C13—H13B | 0.9700 |
C1—H1C | 0.9600 | C14—C15 | 1.363 (2) |
C2—C3 | 1.494 (2) | C14—C19 | 1.428 (2) |
C3—C8 | 1.371 (2) | C15—C16 | 1.403 (2) |
C3—C4 | 1.419 (2) | C15—H15 | 0.9300 |
C4—C5 | 1.352 (2) | C16—C17 | 1.354 (2) |
C4—H4 | 0.9300 | C16—H16 | 0.9300 |
C5—C6 | 1.411 (2) | C17—C18 | 1.407 (2) |
C5—H5 | 0.9300 | C17—H17 | 0.9300 |
C6—C7 | 1.414 (2) | C18—C23 | 1.412 (2) |
C6—C12 | 1.415 (2) | C18—C19 | 1.423 (2) |
C7—C9 | 1.413 (2) | C19—C20 | 1.414 (2) |
C7—C8 | 1.414 (2) | C20—C21 | 1.360 (2) |
C8—H8 | 0.9300 | C20—H20 | 0.9300 |
C9—C10 | 1.362 (2) | C21—C22 | 1.396 (3) |
C9—H9 | 0.9300 | C21—H21 | 0.9300 |
C10—C11 | 1.392 (3) | C22—C23 | 1.353 (3) |
C10—H10 | 0.9300 | C22—H22 | 0.9300 |
C11—C12 | 1.357 (3) | C23—H23 | 0.9300 |
C2—N1—C13 | 120.48 (14) | C11—C12—H12 | 119.5 |
C2—C1—H1A | 109.5 | C6—C12—H12 | 119.5 |
C2—C1—H1B | 109.5 | N1—C13—C14 | 112.15 (13) |
H1A—C1—H1B | 109.5 | N1—C13—H13A | 109.2 |
C2—C1—H1C | 109.5 | C14—C13—H13A | 109.2 |
H1A—C1—H1C | 109.5 | N1—C13—H13B | 109.2 |
H1B—C1—H1C | 109.5 | C14—C13—H13B | 109.2 |
N1—C2—C3 | 116.57 (14) | H13A—C13—H13B | 107.9 |
N1—C2—C1 | 124.74 (14) | C15—C14—C19 | 119.14 (14) |
C3—C2—C1 | 118.67 (14) | C15—C14—C13 | 121.04 (14) |
C8—C3—C4 | 117.77 (14) | C19—C14—C13 | 119.80 (14) |
C8—C3—C2 | 122.67 (14) | C14—C15—C16 | 121.58 (15) |
C4—C3—C2 | 119.55 (14) | C14—C15—H15 | 119.2 |
C5—C4—C3 | 121.60 (15) | C16—C15—H15 | 119.2 |
C5—C4—H4 | 119.2 | C17—C16—C15 | 120.43 (16) |
C3—C4—H4 | 119.2 | C17—C16—H16 | 119.8 |
C4—C5—C6 | 121.26 (15) | C15—C16—H16 | 119.8 |
C4—C5—H5 | 119.4 | C16—C17—C18 | 120.57 (16) |
C6—C5—H5 | 119.4 | C16—C17—H17 | 119.7 |
C5—C6—C7 | 118.31 (14) | C18—C17—H17 | 119.7 |
C5—C6—C12 | 123.17 (16) | C17—C18—C23 | 121.84 (16) |
C7—C6—C12 | 118.52 (16) | C17—C18—C19 | 119.29 (15) |
C9—C7—C6 | 119.01 (15) | C23—C18—C19 | 118.86 (15) |
C9—C7—C8 | 122.07 (15) | C20—C19—C18 | 117.78 (14) |
C6—C7—C8 | 118.91 (14) | C20—C19—C14 | 123.25 (14) |
C3—C8—C7 | 122.14 (15) | C18—C19—C14 | 118.96 (14) |
C3—C8—H8 | 118.9 | C21—C20—C19 | 121.34 (16) |
C7—C8—H8 | 118.9 | C21—C20—H20 | 119.3 |
C10—C9—C7 | 120.45 (17) | C19—C20—H20 | 119.3 |
C10—C9—H9 | 119.8 | C20—C21—C22 | 120.60 (18) |
C7—C9—H9 | 119.8 | C20—C21—H21 | 119.7 |
C9—C10—C11 | 120.66 (17) | C22—C21—H21 | 119.7 |
C9—C10—H10 | 119.7 | C23—C22—C21 | 119.98 (17) |
C11—C10—H10 | 119.7 | C23—C22—H22 | 120.0 |
C12—C11—C10 | 120.44 (17) | C21—C22—H22 | 120.0 |
C12—C11—H11 | 119.8 | C22—C23—C18 | 121.44 (17) |
C10—C11—H11 | 119.8 | C22—C23—H23 | 119.3 |
C11—C12—C6 | 120.91 (18) | C18—C23—H23 | 119.3 |
C13—N1—C2—C3 | 178.47 (14) | C7—C6—C12—C11 | −0.6 (3) |
C13—N1—C2—C1 | 0.0 (3) | C2—N1—C13—C14 | 149.71 (16) |
N1—C2—C3—C8 | 164.24 (15) | N1—C13—C14—C15 | −15.1 (2) |
C1—C2—C3—C8 | −17.2 (2) | N1—C13—C14—C19 | 166.58 (14) |
N1—C2—C3—C4 | −15.2 (2) | C19—C14—C15—C16 | 0.3 (2) |
C1—C2—C3—C4 | 163.37 (16) | C13—C14—C15—C16 | −177.94 (16) |
C8—C3—C4—C5 | −0.3 (2) | C14—C15—C16—C17 | −1.4 (3) |
C2—C3—C4—C5 | 179.17 (15) | C15—C16—C17—C18 | 1.2 (3) |
C3—C4—C5—C6 | −0.3 (3) | C16—C17—C18—C23 | 178.90 (16) |
C4—C5—C6—C7 | 0.5 (2) | C16—C17—C18—C19 | 0.0 (3) |
C4—C5—C6—C12 | −179.04 (16) | C17—C18—C19—C20 | 179.39 (15) |
C5—C6—C7—C9 | −179.49 (14) | C23—C18—C19—C20 | 0.4 (2) |
C12—C6—C7—C9 | 0.1 (2) | C17—C18—C19—C14 | −1.0 (2) |
C5—C6—C7—C8 | 0.0 (2) | C23—C18—C19—C14 | −179.92 (14) |
C12—C6—C7—C8 | 179.53 (14) | C15—C14—C19—C20 | −179.58 (15) |
C4—C3—C8—C7 | 0.8 (2) | C13—C14—C19—C20 | −1.3 (2) |
C2—C3—C8—C7 | −178.68 (14) | C15—C14—C19—C18 | 0.8 (2) |
C9—C7—C8—C3 | 178.83 (15) | C13—C14—C19—C18 | 179.11 (15) |
C6—C7—C8—C3 | −0.6 (2) | C18—C19—C20—C21 | −0.2 (2) |
C6—C7—C9—C10 | 0.5 (2) | C14—C19—C20—C21 | −179.79 (16) |
C8—C7—C9—C10 | −178.91 (16) | C19—C20—C21—C22 | −0.1 (3) |
C7—C9—C10—C11 | −0.7 (3) | C20—C21—C22—C23 | 0.2 (3) |
C9—C10—C11—C12 | 0.2 (3) | C21—C22—C23—C18 | 0.1 (3) |
C10—C11—C12—C6 | 0.5 (3) | C17—C18—C23—C22 | −179.36 (18) |
C5—C6—C12—C11 | 178.97 (17) | C19—C18—C23—C22 | −0.4 (3) |
Cg1, Cg2 and Cg3 are the centroids of the C18–C23, C3–C8 and C6–C12 rings, respectively, |
D—H···A | D—H | H···A | D···A | D—H···A |
C9—H9···Cg1i | 0.93 | 3.00 | 3.5739 (18) | 122 |
C16—H16···Cg2ii | 0.93 | 2.84 | 3.5147 (18) | 130 |
C17—H17···Cg3ii | 0.93 | 2.84 | 3.5626 (19) | 135 |
Symmetry codes: (i) −x, −y+1, −z+1; (ii) −x+1, −y+1, −z+1. |
Experimental details
Crystal data | |
Chemical formula | C23H19N |
Mr | 309.39 |
Crystal system, space group | Triclinic, P1 |
Temperature (K) | 296 |
a, b, c (Å) | 6.6304 (5), 7.7772 (5), 16.7587 (9) |
α, β, γ (°) | 77.655 (3), 87.969 (2), 85.734 (3) |
V (Å3) | 841.69 (9) |
Z | 2 |
Radiation type | Mo Kα |
µ (mm−1) | 0.07 |
Crystal size (mm) | 0.17 × 0.07 × 0.04 |
Data collection | |
Diffractometer | Bruker X8 Kappa APEXII CCD diffractometer |
Absorption correction | Multi-scan (SADABS; Sheldrick, 1998) |
Tmin, Tmax | 0.988, 0.997 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 14750, 2986, 2021 |
Rint | 0.045 |
(sin θ/λ)max (Å−1) | 0.600 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.044, 0.121, 1.02 |
No. of reflections | 2986 |
No. of parameters | 218 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.13, −0.16 |
Computer programs: APEX2 (Bruker, 2006), SAINT-Plus (Bruker, 2005), SHELXTL (Sheldrick, 2008), DIAMOND (Brandenburg, 2009).
Cg1, Cg2 and Cg3 are the centroids of the C18–C23, C3–C8 and C6–C12 rings, respectively, |
D—H···A | D—H | H···A | D···A | D—H···A |
C9—H9···Cg1i | 0.93 | 3.00 | 3.5739 (18) | 122 |
C16—H16···Cg2ii | 0.93 | 2.84 | 3.5147 (18) | 130 |
C17—H17···Cg3ii | 0.93 | 2.84 | 3.5626 (19) | 135 |
Symmetry codes: (i) −x, −y+1, −z+1; (ii) −x+1, −y+1, −z+1. |
Acknowledgements
We are grateful to the Fundação para a Ciência e a Tecnologia (FCT, Portugal), the European Union, QREN, FEDER, COMPETE and the Laboratório Associado Centro de Investigação em Materiais Cerâmicos e Compósitos, CICECO (PEst-C/CTM/LA0011/2011), for their general financial support. We further wish to thank the FCT for funding the R&D project PTDC/QUI-QUI/098098/2008 (FCOMP-01–0124-FEDER-010785), and for the post-doctoral research grants Nos. SFRH/BPD/63736/2009 (to JAF) and SFRH/BPD/46473/2008 (to SMB). Thanks are also due to the FCT for specific funding toward the purchase of the single-crystal diffractometer.
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This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.
Imines, azomethines or Schiff bases, are used as synonyms for the same species, with the general form RR'C═NR''. These species are generally obtained by condensation of the corresponding primary amines (R''NH2) with aldehydes (R'HC═O) or ketones (RR'C═O), and can be additionaly referred to as aldimines and ketimines, respectively (Norton et al., 1954; Hampe et al., 2004). These compounds are stable only when the R, R', and R'' groups are relatively large.
As free ligands, imines have diverse applications: as protecting groups for the C═O double bond or the amine function; as chiral auxiliaries in asymmetric substitution reactions of amino acids; as reagents for the quantitative transformation of aldimines into aza-enolates; the synthesis of primary and secondary amines by reduction of the C═N double bond (Hampe et al., 2004). They can also form complexes with various metals (e.g., Mg, Mn, Co, Cr, Zn Pd, Pt) with application as catalysts of polymerization reactions (e.g., polymerization of lactide; copolymerization of CO2 and epoxides), epoxidation of alkenes and for the Heck reaction between methyl acrylate and p-iodonitrobenzene (Hampe et al., 2004; Kumar et al., 2008).
The title compound was the isolated product of the reaction of [Eu(nta)3(PzPy)] {with Hnta=1-(2-naphthoyl)-3,3,3-trifluoroacetone and PzPy = 2-[3(5)-pyrazolyl]pyridine} with 1-naphthylmethylamine. We believe that this unexpected compound was the product of the reaction of nta- with the amine catalyzed by the presence of the rare-earth metal center. The presence of the metal is essential because the non-catalyzed reaction of β-diketonates with amines does not produce monoimines (Filyakova et al., 1996).
The asymmetric unit of the title compound is composed of a whole molecular unit, C23H19N (see Scheme and Figure 1). The naphthyl groups are planar with mean e. s. d. from planarity of 0.007 and 0.011 Å, for 1- and 2-naphthyl, respectively. The CH3—C═N—CH2 moiety is also planar with almost null deviation [mean e.s. d. = 0.002 Å], and the angles subtended by this moiety with the 1-naphthyl and 2-naphthyl groups are 38.69 (11) and 16.50 (11)°, respectively. The close packing of the molecules in the triclinic centrosymmetric space group is mediated by the need to fill the space in conjunction with several supramolecular weak interactions, such as C—H···π (Figure 2; see Table 1 for geometrical details of these supramolecular interactions). Individual molecules are disposed in zigzag-type forming supramolecular layers which are perpendicular to the [100] direction of the unit cell (Figure 2).