2-(7-Hydr­oxy-2-naphth­yloxy)-N-(6-methyl-2-pyrid­yl)acetamide

Hoong-Kun Fun; Samuel Robinson Jebas; Subrata Jana; Rinku Chakrabarty; Shyamaprasad Goswami

doi:10.1107/S1600536808006211

. 2008 Mar 12;64(Pt 4):o699. doi: 10.1107/S1600536808006211

2-(7-Hydroxy-2-naphthyloxy)-N-(6-methyl-2-pyridyl)acetamide

Hoong-Kun Fun ^a,^*, Samuel Robinson Jebas ^a,^‡, Subrata Jana ^b, Rinku Chakrabarty ^b, Shyamaprasad Goswami ^b

PMCID: PMC2961012 PMID: 21202090

Abstract

In the title compound, C₁₈H₁₆N₂O₃, the dihedral angle between the naphthalene ring system and the pyridyl ring is 18.1 (8)°. The molecules are interconnected via C—H⋯O and O—H⋯O hydrogen bonds. Inversion-related molecules are linked by O—H⋯O hydrogen bonds into cyclic centrosymmetric R ₂ ²(22) dimers. Intramolecular N—H⋯O hydrogen bonding produces an S(5) ring motif. The crystal structure is further stabilized by weak C—H—π interactions.

Related literature

For related literature on the applications; see: Atwood et al. (1996 ▶); Garcia-Tellado et al. (1990 ▶); Ghosh & Masanta (2006 ▶). For comparison bond lengths and angles see: Jin & Jin (2005 ▶); Liu & Li (2004 ▶); Rozycka-Sokolowska et al. (2004 ▶).

Experimental

Crystal data

C₁₈H₁₆N₂O₃
M _r = 308.33
Triclinic,
a = 5.3676 (3) Å
b = 11.6991 (7) Å
c = 12.2915 (6) Å
α = 104.994 (4)°
β = 94.777 (3)°
γ = 94.877 (4)°
V = 738.42 (7) Å³
Z = 2
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 100.0 (1) K
0.4 × 0.16 × 0.09 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T _min = 0.963, T _max = 0.992
12299 measured reflections
3340 independent reflections
2480 reflections with I > 2σ(I)
R _int = 0.046

Refinement

R[F ² > 2σ(F ²)] = 0.045
wR(F ²) = 0.130
S = 1.08
3340 reflections
217 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.24 e Å⁻³
Δρ_min = −0.31 e Å⁻³

Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: APEX2; data reduction: SAINT (Bruker, 2005 ▶); program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2003 ▶).

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808006211/ng2430sup1.cif

e-64-0o699-sup1.cif^{(18.2KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808006211/ng2430Isup2.hkl

e-64-0o699-Isup2.hkl^{(160.5KB, hkl)}

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
C11—H11B⋯O3ⁱ	0.97	2.45	3.410 (2)	168
N1—H1N1⋯O1	0.88 (2)	2.11 (2)	2.5688 (18)	111.9 (16)
O3—H1O3⋯O2ⁱⁱ	0.88 (3)	1.85 (2)	2.6575 (17)	152 (2)
C11—H11A⋯Cg1ⁱⁱⁱ	0.97	2.63	3.438	141
C18—H18A⋯Cg2^iv	0.97	2.92	3.805	153

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Symmetry codes: (i) Inline graphic ; (ii) ; (iii) ; (iv) . Cg1 is the centroid of the C1,C2,C7–C10 ring and Cg2 is the centroid of C2–C7 ring.

Acknowledgments

FHK and SRJ thank the Malaysian Government and Universiti Sains Malaysia for the Science Fund grant No. 305/PFIZIK/613312. SRJ thanks the Universiti Sains Malaysia for the awarding of a post-doctoral research fellowship. SG thanks the CSIR and DST for financial support. RC thanks the CSIR for a research fellowship.

supplementary crystallographic information

Comment

Pyridine amide moiety is widely used for the recognition of carboxylic acid functional group due to its complementary donor-acceptor arrangement (Garcia-Tellado et al., 1990). This group attached with different spacer having photo physical properties is the current interest for the recognition studies of both mono/di carboxylic acids (Ghosh & Masanta, 2006).This type of compounds is also important for its unique supramolecular arrangement (Atwood et al., 1996).

The asymmetric unit of (I) contains one molecule of 2–(7-hydroxy– naphthalene-2-yloxy)-N-(6-methyl-pyridine–2–yl) –acetamide. The dihedral angle between the naphthalene ring and the pyridine rings being 18.03 (8)°. The bond lengths and bond angles are comparable with the values reported in the literature (Rozycka-Sokolowska et al., 2004; Jin & Jin, 2005). The bond distance of C12=O2 is 1.226 (2) Å, which is typical for double bonds (Liu & Li., 2004). The naphthalene ring is planar, the maximum deviation from the least squares plane being -0.011 (2) Å for atom C10. The pyridine ring is planar with the maximum deviation from planarity being -0.010 (2) Å for atom C17.

The molecules are stacked into layers parallel to the bc-plane by C11—H11B—O3ⁱ and O3—H1O3—O2ⁱⁱ hydrogen bonds (Fig. 2). In the crystal structure of (I), inversion-related molecules at (x,y,z) and (2 - x,1 - y,3 - z) are linked by O3—H1O3—O2 hydrogen bonds into cyclic centrosymmetric R₂²(22) dimers. The crystal structure is further stabilized by weak C—H—π interactions involving rings C11—H11A—Cg1 (where Cg1 is the centroid of the C1,C2,C7—C10 ring) and C18—H18A—Cg2 (where Cg2 is the centroid of C2—C7 ring). The molecular conformation is stabilized by a N1—H1N1—O1 intramolecular interaction generating a ring motif S(5).

Experimental

2,7-Dihydroxynaphthalene (160 mg, 1.0 mmol) and N–picolylchloroacetamide (185 mg, 1.0 mmol) were stirred with K₂CO₃ (345 mg, 2.5 mmol) and ^tBu4N⁺Br^- (50 mg, 0.16 mmol) in dry acetone (10 ml) for 7 h at room temperature. Acetone was then distilled off and the crude product was extracted with CHCl₃ (4 x 20 ml) after washing with water. The product (I) was purified by column chromatography (Silica gel 100–200 mesh) using 20% ethyl acetate in pet ether as eluent to afford an off-white coloured solid compound (Yield 61%). Single crystals were grown by slow evaporation of CHCl₃/MeOH/Xylene solution (v/v 1:1:3) (Mp. 178–80 °C).