4-(Adamantan-1-yl)-2-(4-fluoro­phen­yl)quinoline

Zuzana Kozubková; Eva Babjaková; Peter Bartoš; Robert Vícha

doi:10.1107/S1600536813012336

. 2013 May 15;69(Pt 6):o882. doi: 10.1107/S1600536813012336

4-(Adamantan-1-yl)-2-(4-fluorophenyl)quinoline

Zuzana Kozubková ^a, Eva Babjaková ^a, Peter Bartoš ^b, Robert Vícha ^a,^*

PMCID: PMC3685039 PMID: 23795058

Abstract

In the molecule of the title compound, C₂₅H₂₄FN, the dihedral angle between the best planes of the quinoline fragment (rings A and B) and the benzene ring (C) is 9.51 (4)°. In the crystal, molecules are linked into centrosymmetric dimers via pairs of weak C—H⋯F interactions. The molecules are stacked into chains along the a axis by weak off-set π–π interactions between the A and C rings of translation-related molecules with a centroid–centroid distance of 3.6440 (2) Å.

Related literature

For the preparation and spectroscopic properties of the title compound, see: Kozubková et al. (2012 ▶). For related structures, see: Kozubková et al. (2012 ▶); Prabhuswamy et al. (2012 ▶). For the biological activity of related compounds, see: Nayyar et al. (2009 ▶).

Experimental

Crystal data

C₂₅H₂₄FN
M _r = 357.45
Triclinic,
a = 6.4604 (3) Å
b = 10.9964 (4) Å
c = 12.9074 (5) Å
α = 93.205 (3)°
β = 96.446 (3)°
γ = 100.507 (3)°
V = 893.14 (6) Å³
Z = 2
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 120 K
0.60 × 0.40 × 0.20 mm

Data collection

Oxford Diffraction Xcalibur diffractometer
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009 ▶) T _min = 0.971, T _max = 1.000
9490 measured reflections
3142 independent reflections
2445 reflections with I > 2σ(I)
R _int = 0.015

Refinement

R[F ² > 2σ(F ²)] = 0.034
wR(F ²) = 0.099
S = 1.08
3142 reflections
244 parameters
H-atom parameters constrained
Δρ_max = 0.20 e Å⁻³
Δρ_min = −0.19 e Å⁻³

Data collection: CrysAlis CCD (Oxford Diffraction, 2009 ▶); cell refinement: CrysAlis RED (Oxford Diffraction, 2009 ▶); data reduction: CrysAlis RED; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ▶) and Mercury (Macrae et al., 2008 ▶); software used to prepare material for publication: SHELXL97.

Supplementary Material

Click here for additional data file.^{(23.2KB, cif)}

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536813012336/fy2093sup1.cif

e-69-0o882-sup1.cif^{(23.2KB, cif)}

Click here for additional data file.^{(154.1KB, hkl)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813012336/fy2093Isup2.hkl

e-69-0o882-Isup2.hkl^{(154.1KB, hkl)}

Click here for additional data file.^{(7.5KB, cml)}

Supplementary material file. DOI: 10.1107/S1600536813012336/fy2093Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Table 1. Hydrogen-bond geometry (Å, °).

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C12—H12⋯F1ⁱ	0.95	2.61	3.2955 (12)	129

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Symmetry code: (i) Inline graphic .

Acknowledgments

The financial support of this work by the Internal Founding Agency of Tomas Bata University in Zlin (project No. IGA/FT/2013/008) is gratefully acknowledged.

supplementary crystallographic information

Comment

Quinoline and its derivatives are very important compounds whose structures occur in a variety of natural alkaloids and therapeutics with interesting biological activities. As an example, derivatives of 4-(1-adamantyl)quinoline-2-carboxylic acid have been recently described as potent antituberculosis agents (Nayyar et al., 2009). The title compound was prepared as a part of our research aimed at the examination of novel convenient synthetic procedures toward 4-(1-adamantyl)quinoline derivatives (Kozubková et al., 2012).

The molecule of the title compound consists of three motifs – quinoline and benzene rings and adamantane cage (Figure 1). The quinoline and benzene rings are essentially planar with the respective r.m.s. deviations of 0.0303 and 0.0052 Å and the respective maximum deviations of -0.0477 (12) Å for C1 and 0.0067 (12) Å for C13. The dihedral angle between the planes of these rings is 9.51 (4)°. The adamantane cage consist of free fused cyclohexane rings in classical chairs conformations with C—C—C angles in the range 105.68 (10)–111.83 (11)°. The torsion angles describing the mutual orientation of the benzene, quinoline and adamantane moieties C2–C1–C10–C15 and C4–C3–C16–C17 are -10.62 (19) and 66.77 (15)°, respectively. Although the quinoline ring is essentially planar, it is markedly deformed in plane as it is usual for similar quinoline rings substituted with bulky adamantane at position 4 (Kozubková et al., 2012). The most affected valence angles N1–C9–C8, C2–C3–C4, N1–C9–C4 and C3–C4–C5 are 115.82 (11), 115.91 (11), 124.06 (12) and 125.91 (12)°, respectively. The packing of the molecules in the crystal is stabilized by a weak C—H···F interaction (Table 1, Figure 2). In addition, a weak π–π interaction (Figure 2) is observed between the benzene ring (C10–C15) and quinoline ring (C1–C9, N1), with the shortest centroid-to-centroid distance of 3.6440 (2) Å. Distances of C14, C15, and Cg1 from best plane of adjacent quinoline ring are -3.2742 (13), -3.2448 (13), and -3.4517 (13) Å.

Experimental

The title compound was prepared via a Friedländer reaction from the corresponding 1-adamantyl aminophenyl ketone and 4-fluoroacetophenone as it has been described previously (Kozubková et al., 2012). A single-crystal usable for X-ray analysis was obtained by slow spontaneous evaporation from deuterochloloform at room temperature.