4-(Prop-2-yn-1-yl­oxy)benzaldehyde

Ikue Doi; Tsunehisa Okuno

doi:10.1107/S1600536812050866

. 2012 Dec 22;69(Pt 1):o125. doi: 10.1107/S1600536812050866

4-(Prop-2-yn-1-yloxy)benzaldehyde

Ikue Doi ^a, Tsunehisa Okuno ^a,^*

PMCID: PMC3588297 PMID: 23476386

Abstract

In the title molecule, C₁₀H₈O₂, all non-H atoms are essentailly coplanar (r.m.s. deviation = 0.0192 Å), indicating an effective conjugation of the carbonyl group, the benzene ring and the lone pair of the propynyloxy O atom. In the crystal, π–π stacking interactions [centroid–centroid distance = 3.5585 (15) Å] connect molecules into inversion dimers which are linked by Csp—H⋯O=C hydrogen bonds, forming a ladder-like structure.

Related literature

For related structures of 4-(prop-2-yn-1-yloxy)benzenes, see: Berscheid et al. (1992 ▶); Mohr et al. (2003 ▶); Nieger et al. (2004 ▶); Ranjith et al. (2010 ▶); Zhang et al. (2011 ▶). graphic file with name e-69-0o125-scheme1.jpg

Experimental

Crystal data

C₁₀H₈O₂
M _r = 160.17
Monoclinic,
a = 7.906 (3) Å
b = 7.385 (2) Å
c = 14.036 (5) Å
β = 102.025 (5)°
V = 801.5 (5) Å³
Z = 4
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 93 K
0.20 × 0.10 × 0.10 mm

Data collection

Rigaku Saturn724+ diffractometer
Absorption correction: numerical (NUMABS; Rigaku, 1999 ▶) T _min = 0.984, T _max = 0.991
6309 measured reflections
1832 independent reflections
1669 reflections with F ² > 2σ(F ²)
R _int = 0.044

Refinement

R[F ² > 2σ(F ²)] = 0.037
wR(F ²) = 0.101
S = 1.06
1831 reflections
141 parameters
H-atom parameters constrained
Δρ_max = 0.32 e Å⁻³
Δρ_min = −0.17 e Å⁻³

Data collection: CrystalClear (Rigaku, 2008 ▶); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXD (Schneider & Sheldrick, 2002 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 2012 ▶); software used to prepare material for publication: CrystalStructure (Rigaku, 2010 ▶).

Supplementary Material

Click here for additional data file.^{(19.1KB, cif)}

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812050866/lh5571sup1.cif

e-69-0o125-sup1.cif^{(19.1KB, cif)}

Click here for additional data file.^{(90.2KB, hkl)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812050866/lh5571Isup2.hkl

e-69-0o125-Isup2.hkl^{(90.2KB, hkl)}

Click here for additional data file.^{(3.1KB, cml)}

Supplementary material file. DOI: 10.1107/S1600536812050866/lh5571Isup3.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
C10—H10⋯O1ⁱ	0.95	2.23	3.1575 (14)	166

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Symmetry code: (i) Inline graphic .

Acknowledgments

This work was supported by the Research for Promoting Technological Seeds from the Japan Science and Technology Agency (JST).

supplementary crystallographic information

Comment

The title compound, C₁₀H₈O₂, is a benzaldehyde derivative whose structure is often observed in macrocyclic compounds (Berscheid et al. 1992; Mohr et al. 2003). Analogues of the title compound have already been reported as an ester (Nieger et al., 2004), as a ketone (Ranjith et al., 2010) and as an α,β-unsatuated ketone (Zhang et al., 2011). The molecule has a planar structure (atoms C1—C10/O1—O2 are essentailly co-planar with an r.m.s. deviation = 0.0192 Å), indicating an effective conjugation of the carbonyl group, the C1—C6 benzene ring and the lone pair of atom O2.

The molecular structure of the title compound is shown in Fig. 1. In the crystal, molecules form dimers across inversion centers (Fig. 2), owing to π–π stacking interactions. The intermolecular distance of C4···C6ⁱⁱⁱ is 3.3026 (16) Å [Symmetry code:(iii) -x + 1, -y + 1, -z + 2.]. The molecules also form weak intermolecular C—H···O═C hydrogen bonds between the carbonyl oxygen and acetylene group to give a ladder-like structure where the distances of C10···O1ⁱ and O1···C10ⁱⁱ are 3.1575 (14) Å [Symmetry codes:(i) x + 3/2, -y + 1/2, z + 1/2 and (ii) x - 3/2, -y + 1/2, z - 1/2.].

Experimental

A mixture of 4-hydroxybenzaldehyde (1.22 g, 10 mmol) and 3-bromoprop-1-yne (3.57 g, 30 mmol) in 1-methylpyrrolidin-2-one (20 ml) was heated at 473K for 2 h in the presence of K₂CO₃ (4.15 g). The solution was poured into water and extracted by benzene (100 ml). The organic layer was washed with 5% NaOHaq, 5% Na₂CO₃aq and water, and was dried over Na₂SO₄. After removal of Na₂SO₄ and benzene, the residue was recrystallized by hexane to give 0.96 g (60%) of the title compound as a pale yellow powder. Single crystals with sufficient quality were prepared by sublimation at room temperature.