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ISSN: 2056-9890

[(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

(Received 11 August 2012; accepted 2 October 2012; online 20 October 2012)

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 ketimines, see: Norton et al. (1954[Norton, D. G., Haury, V. E., Davis, F. C., Mitchell, L. J. & Ballard, S. A. (1954). J. Org. Chem. 19, 1054-1066.]); Hampe et al. (2004[Hampe, D., Günther, W., Görls, H. & Anders, E. (2004). Eur. J. Org. Chem. pp. 4357-4372.]) and references cited therein; Kumar et al. (2008[Kumar, A., Agarwal, M. & Singh, A. K. (2008). Polyhedron, 27, 485-492.]). For general background to β-diketonates, see: Bruno et al. (2008[Bruno, S. M., Ferreira, R. A. S., Carlos, L. D., Pillinger, M., Ribeiro-Claro, P. & Gonçalves, I. S. (2008). Microporous Mesoporous Mater. 113, 453-462.]). Filyakova et al. (1996[Filyakova, V. I., Ratner, V. G., Karpenko, N. S. & Pashkevich, K. I. (1996). Russ. Chem. Bull. 45, 2278-2284.]).

[Scheme 1]

Experimental

Crystal data
  • C23H19N

  • Mr = 309.39

  • Triclinic, [P \overline 1]

  • a = 6.6304 (5) Å

  • b = 7.7772 (5) Å

  • c = 16.7587 (9) Å

  • α = 77.655 (3)°

  • β = 87.969 (2)°

  • γ = 85.734 (3)°

  • V = 841.69 (9) Å3

  • Z = 2

  • Mo Kα radiation

  • μ = 0.07 mm−1

  • T = 296 K

  • 0.17 × 0.07 × 0.04 mm

Data collection
  • Bruker X8 Kappa APEXII CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 1998[Sheldrick, G. M. (1998). SADABS. Bruker AXS, Inc. Madison, Wisconsin, USA.]) Tmin = 0.988, Tmax = 0.997

  • 14750 measured reflections

  • 2986 independent reflections

  • 2021 reflections with I > 2σ(I)

  • Rint = 0.045

Refinement
  • R[F2 > 2σ(F2)] = 0.044

  • wR(F2) = 0.121

  • S = 1.02

  • 2986 reflections

  • 218 parameters

  • H-atom parameters constrained

  • Δρmax = 0.13 e Å−3

  • Δρmin = −0.16 e Å−3

Table 1
Selected short distance interactions (Å, °)

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 DA 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.

Data collection: APEX2 (Bruker, 2006[Bruker (2006). APEX2. Bruker AXS, Delft, The Netherlands.]); cell refinement: SAINT-Plus (Bruker, 2005[Bruker (2005). SAINT-Plus. Bruker AXS, Inc. Madison, Wisconsin, USA.]); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXTL; molecular graphics: DIAMOND (Brandenburg, 2009[Brandenburg, K. (2009). DIAMOND. Crystal Impact GbR, Bonn, Germany.]); software used to prepare material for publication: SHELXTL.

Supporting information


Comment top

Imines, azomethines or Schiff bases, are used as synonyms for the same species, with the general form RR'CNR''. These species are generally obtained by condensation of the corresponding primary amines (R''NH2) with aldehydes (R'HCO) or ketones (RR'CO), 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 CO 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 CN 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—CN—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).

Related literature top

For general background to aldimidines and ketimines, see: Norton 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).

Experimental top

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).

Refinement top

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.

Computing details top

Data collection: APEX2 (Bruker, 2006); cell refinement: 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).

Figures top
[Figure 1] Fig. 1. Asymmetric unit of the title compound showing all non-hydrogen atoms represented as thermal displacement ellipsoids drawn at the 30% probability level, and hydrogen atoms as small spheres with arbitrary radius.
[Figure 2] Fig. 2. Crystal packing of the title compound viewed in perspective along the (a) [100] and (b) [001] directions of the unit cell. C—H···π supramolecular interactions are depicted as dashed green lines.
[(E)-1-(Naphthalen-2-yl)ethylidene](naphthalen-1-ylmethyl)amine top
Crystal data top
C23H19NZ = 2
Mr = 309.39F(000) = 328
Triclinic, P1Dx = 1.221 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 6.6304 (5) ÅCell parameters from 4208 reflections
b = 7.7772 (5) Åθ = 2.5–24.2°
c = 16.7587 (9) ŵ = 0.07 mm1
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
Data collection top
Bruker X8 Kappa APEXII CCD
diffractometer
2986 independent reflections
Radiation source: fine-focus sealed tube2021 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.045
ω / ϕ scansθmax = 25.2°, θmin = 3.7°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1998)
h = 77
Tmin = 0.988, Tmax = 0.997k = 99
14750 measured reflectionsl = 1920
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.044Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.121H-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 parametersΔρmax = 0.13 e Å3
0 restraintsΔρmin = 0.16 e Å3
Crystal data top
C23H19Nγ = 85.734 (3)°
Mr = 309.39V = 841.69 (9) Å3
Triclinic, P1Z = 2
a = 6.6304 (5) ÅMo Kα radiation
b = 7.7772 (5) ŵ = 0.07 mm1
c = 16.7587 (9) ÅT = 296 K
α = 77.655 (3)°0.17 × 0.07 × 0.04 mm
β = 87.969 (2)°
Data collection top
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 = 0.997Rint = 0.045
14750 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0440 restraints
wR(F2) = 0.121H-atom parameters constrained
S = 1.02Δρmax = 0.13 e Å3
2986 reflectionsΔρmin = 0.16 e Å3
218 parameters
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
xyzUiso*/Ueq
N10.1658 (2)0.2127 (2)0.47556 (8)0.0604 (4)
C10.1836 (3)0.2591 (3)0.52396 (10)0.0730 (6)
H1A0.20920.38490.50910.109*
H1B0.25310.21450.57450.109*
H1C0.23130.20660.48190.109*
C20.0396 (2)0.2145 (2)0.53387 (9)0.0486 (4)
C30.1216 (2)0.16403 (19)0.61818 (9)0.0452 (4)
C40.3175 (2)0.0775 (2)0.63052 (9)0.0531 (4)
H40.39180.05190.58590.064*
C50.3988 (3)0.0313 (2)0.70559 (10)0.0576 (4)
H50.52740.02580.71150.069*
C60.2923 (2)0.0681 (2)0.77506 (9)0.0517 (4)
C70.0964 (2)0.1538 (2)0.76454 (9)0.0475 (4)
C80.0156 (2)0.1991 (2)0.68525 (9)0.0485 (4)
H80.11380.25440.67840.058*
C90.0116 (3)0.1929 (2)0.83342 (10)0.0598 (5)
H90.14100.24840.82730.072*
C100.0725 (3)0.1499 (3)0.90866 (10)0.0707 (5)
H100.00040.17740.95340.085*
C110.2652 (3)0.0652 (3)0.91923 (11)0.0745 (6)
H110.32070.03630.97100.089*
C120.3726 (3)0.0245 (2)0.85451 (10)0.0676 (5)
H120.50070.03280.86250.081*
C130.0991 (3)0.2558 (3)0.39124 (9)0.0681 (5)
H13A0.02100.33630.38720.082*
H13B0.06310.14900.37570.082*
C140.2595 (2)0.33899 (19)0.33304 (9)0.0454 (4)
C150.4228 (2)0.4037 (2)0.36071 (9)0.0514 (4)
H150.43690.39260.41660.062*
C160.5702 (3)0.4866 (2)0.30687 (11)0.0628 (5)
H160.67870.53180.32730.075*
C170.5556 (3)0.5013 (2)0.22524 (11)0.0633 (5)
H170.65550.55460.19020.076*
C180.3907 (2)0.4366 (2)0.19305 (9)0.0511 (4)
C190.2387 (2)0.35522 (19)0.24721 (9)0.0454 (4)
C200.0741 (3)0.2932 (2)0.21271 (10)0.0593 (5)
H200.02690.23930.24690.071*
C210.0605 (3)0.3109 (3)0.13055 (10)0.0720 (5)
H210.04910.26890.10940.086*
C220.2096 (3)0.3916 (3)0.07773 (11)0.0748 (6)
H220.19890.40340.02160.090*
C230.3697 (3)0.4527 (3)0.10818 (10)0.0678 (5)
H230.46800.50650.07240.081*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N10.0528 (9)0.0836 (11)0.0417 (8)0.0104 (7)0.0017 (6)0.0044 (7)
C10.0554 (11)0.1075 (16)0.0545 (11)0.0058 (10)0.0066 (8)0.0166 (10)
C20.0478 (10)0.0500 (10)0.0481 (9)0.0084 (7)0.0025 (8)0.0088 (7)
C30.0459 (9)0.0443 (9)0.0449 (9)0.0070 (7)0.0010 (7)0.0068 (7)
C40.0509 (10)0.0581 (10)0.0507 (9)0.0014 (8)0.0007 (7)0.0136 (8)
C50.0497 (10)0.0610 (11)0.0597 (10)0.0067 (8)0.0062 (8)0.0100 (8)
C60.0569 (10)0.0467 (10)0.0496 (9)0.0038 (8)0.0056 (7)0.0055 (7)
C70.0531 (10)0.0432 (9)0.0451 (9)0.0073 (7)0.0016 (7)0.0064 (7)
C80.0465 (9)0.0457 (9)0.0515 (9)0.0023 (7)0.0013 (7)0.0066 (7)
C90.0669 (11)0.0587 (11)0.0517 (10)0.0020 (9)0.0057 (8)0.0090 (8)
C100.0923 (16)0.0727 (13)0.0460 (10)0.0090 (11)0.0060 (10)0.0103 (9)
C110.0926 (15)0.0816 (14)0.0464 (10)0.0087 (12)0.0118 (10)0.0041 (9)
C120.0712 (12)0.0705 (12)0.0564 (11)0.0004 (10)0.0162 (9)0.0028 (9)
C130.0558 (11)0.1003 (15)0.0451 (10)0.0165 (10)0.0020 (8)0.0045 (9)
C140.0476 (9)0.0443 (9)0.0435 (8)0.0005 (7)0.0019 (7)0.0085 (7)
C150.0540 (10)0.0530 (10)0.0471 (9)0.0033 (8)0.0077 (7)0.0094 (7)
C160.0566 (11)0.0646 (11)0.0666 (11)0.0172 (9)0.0092 (9)0.0071 (9)
C170.0558 (11)0.0669 (12)0.0630 (11)0.0149 (9)0.0056 (8)0.0021 (9)
C180.0563 (10)0.0468 (9)0.0482 (9)0.0004 (8)0.0031 (7)0.0076 (7)
C190.0500 (9)0.0403 (8)0.0456 (8)0.0002 (7)0.0024 (7)0.0095 (7)
C200.0633 (11)0.0650 (11)0.0511 (10)0.0145 (9)0.0032 (8)0.0122 (8)
C210.0822 (14)0.0832 (14)0.0562 (11)0.0186 (11)0.0112 (10)0.0208 (10)
C220.0948 (15)0.0873 (14)0.0448 (10)0.0080 (12)0.0032 (10)0.0187 (9)
C230.0776 (13)0.0777 (13)0.0465 (10)0.0068 (10)0.0106 (9)0.0107 (9)
Geometric parameters (Å, º) top
N1—C21.2650 (19)C11—H110.9300
N1—C131.4575 (19)C12—H120.9300
C1—C21.502 (2)C13—C141.504 (2)
C1—H1A0.9600C13—H13A0.9700
C1—H1B0.9600C13—H13B0.9700
C1—H1C0.9600C14—C151.363 (2)
C2—C31.494 (2)C14—C191.428 (2)
C3—C81.371 (2)C15—C161.403 (2)
C3—C41.419 (2)C15—H150.9300
C4—C51.352 (2)C16—C171.354 (2)
C4—H40.9300C16—H160.9300
C5—C61.411 (2)C17—C181.407 (2)
C5—H50.9300C17—H170.9300
C6—C71.414 (2)C18—C231.412 (2)
C6—C121.415 (2)C18—C191.423 (2)
C7—C91.413 (2)C19—C201.414 (2)
C7—C81.414 (2)C20—C211.360 (2)
C8—H80.9300C20—H200.9300
C9—C101.362 (2)C21—C221.396 (3)
C9—H90.9300C21—H210.9300
C10—C111.392 (3)C22—C231.353 (3)
C10—H100.9300C22—H220.9300
C11—C121.357 (3)C23—H230.9300
C2—N1—C13120.48 (14)C11—C12—H12119.5
C2—C1—H1A109.5C6—C12—H12119.5
C2—C1—H1B109.5N1—C13—C14112.15 (13)
H1A—C1—H1B109.5N1—C13—H13A109.2
C2—C1—H1C109.5C14—C13—H13A109.2
H1A—C1—H1C109.5N1—C13—H13B109.2
H1B—C1—H1C109.5C14—C13—H13B109.2
N1—C2—C3116.57 (14)H13A—C13—H13B107.9
N1—C2—C1124.74 (14)C15—C14—C19119.14 (14)
C3—C2—C1118.67 (14)C15—C14—C13121.04 (14)
C8—C3—C4117.77 (14)C19—C14—C13119.80 (14)
C8—C3—C2122.67 (14)C14—C15—C16121.58 (15)
C4—C3—C2119.55 (14)C14—C15—H15119.2
C5—C4—C3121.60 (15)C16—C15—H15119.2
C5—C4—H4119.2C17—C16—C15120.43 (16)
C3—C4—H4119.2C17—C16—H16119.8
C4—C5—C6121.26 (15)C15—C16—H16119.8
C4—C5—H5119.4C16—C17—C18120.57 (16)
C6—C5—H5119.4C16—C17—H17119.7
C5—C6—C7118.31 (14)C18—C17—H17119.7
C5—C6—C12123.17 (16)C17—C18—C23121.84 (16)
C7—C6—C12118.52 (16)C17—C18—C19119.29 (15)
C9—C7—C6119.01 (15)C23—C18—C19118.86 (15)
C9—C7—C8122.07 (15)C20—C19—C18117.78 (14)
C6—C7—C8118.91 (14)C20—C19—C14123.25 (14)
C3—C8—C7122.14 (15)C18—C19—C14118.96 (14)
C3—C8—H8118.9C21—C20—C19121.34 (16)
C7—C8—H8118.9C21—C20—H20119.3
C10—C9—C7120.45 (17)C19—C20—H20119.3
C10—C9—H9119.8C20—C21—C22120.60 (18)
C7—C9—H9119.8C20—C21—H21119.7
C9—C10—C11120.66 (17)C22—C21—H21119.7
C9—C10—H10119.7C23—C22—C21119.98 (17)
C11—C10—H10119.7C23—C22—H22120.0
C12—C11—C10120.44 (17)C21—C22—H22120.0
C12—C11—H11119.8C22—C23—C18121.44 (17)
C10—C11—H11119.8C22—C23—H23119.3
C11—C12—C6120.91 (18)C18—C23—H23119.3
C13—N1—C2—C3178.47 (14)C7—C6—C12—C110.6 (3)
C13—N1—C2—C10.0 (3)C2—N1—C13—C14149.71 (16)
N1—C2—C3—C8164.24 (15)N1—C13—C14—C1515.1 (2)
C1—C2—C3—C817.2 (2)N1—C13—C14—C19166.58 (14)
N1—C2—C3—C415.2 (2)C19—C14—C15—C160.3 (2)
C1—C2—C3—C4163.37 (16)C13—C14—C15—C16177.94 (16)
C8—C3—C4—C50.3 (2)C14—C15—C16—C171.4 (3)
C2—C3—C4—C5179.17 (15)C15—C16—C17—C181.2 (3)
C3—C4—C5—C60.3 (3)C16—C17—C18—C23178.90 (16)
C4—C5—C6—C70.5 (2)C16—C17—C18—C190.0 (3)
C4—C5—C6—C12179.04 (16)C17—C18—C19—C20179.39 (15)
C5—C6—C7—C9179.49 (14)C23—C18—C19—C200.4 (2)
C12—C6—C7—C90.1 (2)C17—C18—C19—C141.0 (2)
C5—C6—C7—C80.0 (2)C23—C18—C19—C14179.92 (14)
C12—C6—C7—C8179.53 (14)C15—C14—C19—C20179.58 (15)
C4—C3—C8—C70.8 (2)C13—C14—C19—C201.3 (2)
C2—C3—C8—C7178.68 (14)C15—C14—C19—C180.8 (2)
C9—C7—C8—C3178.83 (15)C13—C14—C19—C18179.11 (15)
C6—C7—C8—C30.6 (2)C18—C19—C20—C210.2 (2)
C6—C7—C9—C100.5 (2)C14—C19—C20—C21179.79 (16)
C8—C7—C9—C10178.91 (16)C19—C20—C21—C220.1 (3)
C7—C9—C10—C110.7 (3)C20—C21—C22—C230.2 (3)
C9—C10—C11—C120.2 (3)C21—C22—C23—C180.1 (3)
C10—C11—C12—C60.5 (3)C17—C18—C23—C22179.36 (18)
C5—C6—C12—C11178.97 (17)C19—C18—C23—C220.4 (3)
Hydrogen-bond geometry (Å, º) top
Cg1, Cg2 and Cg3 are the centroids of the C18–C23, C3–C8 and C6–C12 rings, respectively,
D—H···AD—HH···AD···AD—H···A
C9—H9···Cg1i0.933.003.5739 (18)122
C16—H16···Cg2ii0.932.843.5147 (18)130
C17—H17···Cg3ii0.932.843.5626 (19)135
Symmetry codes: (i) x, y+1, z+1; (ii) x+1, y+1, z+1.

Experimental details

Crystal data
Chemical formulaC23H19N
Mr309.39
Crystal system, space groupTriclinic, 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)
V3)841.69 (9)
Z2
Radiation typeMo Kα
µ (mm1)0.07
Crystal size (mm)0.17 × 0.07 × 0.04
Data collection
DiffractometerBruker X8 Kappa APEXII CCD
diffractometer
Absorption correctionMulti-scan
(SADABS; Sheldrick, 1998)
Tmin, Tmax0.988, 0.997
No. of measured, independent and
observed [I > 2σ(I)] reflections
14750, 2986, 2021
Rint0.045
(sin θ/λ)max1)0.600
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.044, 0.121, 1.02
No. of reflections2986
No. of parameters218
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.13, 0.16

Computer programs: APEX2 (Bruker, 2006), SAINT-Plus (Bruker, 2005), SHELXTL (Sheldrick, 2008), DIAMOND (Brandenburg, 2009).

Hydrogen-bond geometry (Å, º) top
Cg1, Cg2 and Cg3 are the centroids of the C18–C23, C3–C8 and C6–C12 rings, respectively,
D—H···AD—HH···AD···AD—H···A
C9—H9···Cg1i0.933.003.5739 (18)122
C16—H16···Cg2ii0.932.843.5147 (18)130
C17—H17···Cg3ii0.932.843.5626 (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.

References

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