organic compounds
4-(Prop-2-yn-1-yloxy)benzaldehyde
aDepartment of Material Science and Chemistry, Wakayama University, Sakaedani, Wakayama 640-8510, Japan
*Correspondence e-mail: okuno@center.wakayama-u.ac.jp
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).
Experimental
Crystal data
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Refinement
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Data collection: CrystalClear (Rigaku, 2008); cell 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).
Supporting information
https://doi.org/10.1107/S1600536812050866/lh5571sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536812050866/lh5571Isup2.hkl
Supporting information file. DOI: https://doi.org/10.1107/S1600536812050866/lh5571Isup3.cml
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
at room temperature.The C-bound H atoms were placed at ideal positions and were refined as riding on their parent C atoms. Uiso(H) values of the H atoms were set at 1.2Ueq(parent atom).
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.].
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).
Data collection: CrystalClear (Rigaku, 2008); cell
CrystalClear (Rigaku, 2008); data reduction: CrystalClear (Rigaku, 2008); 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).C10H8O2 | F(000) = 336.00 |
Mr = 160.17 | Dx = 1.327 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71075 Å |
Hall symbol: -P 2yn | Cell parameters from 2598 reflections |
a = 7.906 (3) Å | θ = 2.6–31.1° |
b = 7.385 (2) Å | µ = 0.09 mm−1 |
c = 14.036 (5) Å | T = 93 K |
β = 102.025 (5)° | Prism, colorless |
V = 801.5 (5) Å3 | 0.20 × 0.10 × 0.10 mm |
Z = 4 |
Rigaku Saturn724+ diffractometer | 1669 reflections with F2 > 2σ(F2) |
Detector resolution: 7.111 pixels mm-1 | Rint = 0.044 |
ω scans | θmax = 27.5° |
Absorption correction: numerical (NUMABS; Rigaku, 1999) | h = −10→10 |
Tmin = 0.984, Tmax = 0.991 | k = −9→8 |
6309 measured reflections | l = −18→13 |
1832 independent reflections |
Refinement on F2 | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.037 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.101 | H-atom parameters constrained |
S = 1.06 | w = 1/[σ2(Fo2) + (0.0503P)2 + 0.2315P] where P = (Fo2 + 2Fc2)/3 |
1831 reflections | (Δ/σ)max = 0.001 |
141 parameters | Δρmax = 0.32 e Å−3 |
0 restraints | Δρmin = −0.17 e Å−3 |
Primary atom site location: structure-invariant direct methods |
C10H8O2 | V = 801.5 (5) Å3 |
Mr = 160.17 | Z = 4 |
Monoclinic, P21/n | Mo Kα radiation |
a = 7.906 (3) Å | µ = 0.09 mm−1 |
b = 7.385 (2) Å | T = 93 K |
c = 14.036 (5) Å | 0.20 × 0.10 × 0.10 mm |
β = 102.025 (5)° |
Rigaku Saturn724+ diffractometer | 1832 independent reflections |
Absorption correction: numerical (NUMABS; Rigaku, 1999) | 1669 reflections with F2 > 2σ(F2) |
Tmin = 0.984, Tmax = 0.991 | Rint = 0.044 |
6309 measured reflections |
R[F2 > 2σ(F2)] = 0.037 | 0 restraints |
wR(F2) = 0.101 | H-atom parameters constrained |
S = 1.06 | Δρmax = 0.32 e Å−3 |
1831 reflections | Δρmin = −0.17 e Å−3 |
141 parameters |
Refinement. Refinement was performed using all reflections. except for one with very negative F2. The weighted R-factor (wR) and goodness of fit (S) are based on F2. R-factor (gt) are based on F. The threshold expression of F2 > 2.0 σ(F2) is used only for calculating R-factor (gt). |
x | y | z | Uiso*/Ueq | ||
O1 | −0.02874 (9) | 0.43434 (11) | 0.86519 (6) | 0.0269 (3) | |
O2 | 0.72238 (8) | 0.20161 (10) | 1.09425 (5) | 0.0184 (2) | |
C1 | 0.26055 (12) | 0.32435 (14) | 0.90578 (7) | 0.0169 (3) | |
C2 | 0.39397 (13) | 0.24978 (14) | 0.86774 (7) | 0.0183 (3) | |
C3 | 0.55122 (13) | 0.20458 (14) | 0.92785 (7) | 0.0176 (3) | |
C4 | 0.57337 (12) | 0.23630 (13) | 1.02780 (7) | 0.0160 (3) | |
C5 | 0.43929 (12) | 0.30938 (13) | 1.06687 (7) | 0.0167 (3) | |
C6 | 0.28397 (12) | 0.35345 (13) | 1.00640 (7) | 0.0171 (3) | |
C7 | 0.09823 (13) | 0.37510 (14) | 0.83968 (7) | 0.0206 (3) | |
C8 | 0.86477 (12) | 0.13260 (14) | 1.05624 (7) | 0.0185 (3) | |
C9 | 1.00867 (12) | 0.09585 (15) | 1.13789 (7) | 0.0198 (3) | |
C10 | 1.12987 (14) | 0.06479 (16) | 1.20170 (8) | 0.0242 (3) | |
H2 | 0.3760 | 0.2314 | 0.7979 | 0.0271* | |
H3 | 0.6428 | 0.1534 | 0.9001 | 0.0187* | |
H5 | 0.4618 | 0.3309 | 1.1384 | 0.0247* | |
H6 | 0.1910 | 0.4060 | 1.0336 | 0.0199* | |
H7 | 0.1033 | 0.3559 | 0.7691 | 0.0267* | |
H8A | 0.8996 | 0.2240 | 1.0127 | 0.0191* | |
H8B | 0.8295 | 0.0199 | 1.0208 | 0.0222* | |
H10 | 1.2291 | 0.0429 | 1.2516 | 0.0372* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0204 (4) | 0.0323 (5) | 0.0256 (5) | 0.0041 (3) | −0.0007 (3) | −0.0039 (3) |
O2 | 0.0168 (4) | 0.0228 (4) | 0.0150 (4) | 0.0031 (3) | 0.0020 (3) | −0.0004 (3) |
C1 | 0.0187 (5) | 0.0144 (5) | 0.0168 (5) | −0.0028 (4) | 0.0016 (4) | 0.0003 (4) |
C2 | 0.0219 (5) | 0.0178 (5) | 0.0149 (5) | −0.0030 (4) | 0.0030 (4) | −0.0011 (4) |
C3 | 0.0194 (5) | 0.0172 (5) | 0.0169 (5) | −0.0003 (4) | 0.0051 (4) | −0.0014 (4) |
C4 | 0.0174 (5) | 0.0134 (5) | 0.0162 (5) | −0.0015 (4) | 0.0015 (4) | 0.0013 (4) |
C5 | 0.0197 (5) | 0.0167 (5) | 0.0138 (5) | −0.0015 (4) | 0.0034 (4) | 0.0004 (4) |
C6 | 0.0177 (5) | 0.0158 (5) | 0.0180 (5) | −0.0007 (4) | 0.0040 (4) | −0.0003 (4) |
C7 | 0.0214 (5) | 0.0203 (5) | 0.0182 (5) | −0.0019 (4) | −0.0004 (4) | −0.0022 (4) |
C8 | 0.0179 (5) | 0.0202 (5) | 0.0177 (5) | 0.0025 (4) | 0.0041 (4) | −0.0002 (4) |
C9 | 0.0196 (5) | 0.0207 (5) | 0.0199 (5) | 0.0007 (4) | 0.0060 (4) | −0.0011 (4) |
C10 | 0.0213 (5) | 0.0303 (6) | 0.0210 (5) | 0.0026 (5) | 0.0045 (4) | −0.0001 (5) |
O1—C7 | 1.2154 (14) | C8—C9 | 1.4622 (13) |
O2—C4 | 1.3659 (11) | C9—C10 | 1.1897 (14) |
O2—C8 | 1.4360 (13) | C2—H2 | 0.970 |
C1—C2 | 1.3913 (16) | C3—H3 | 0.968 |
C1—C6 | 1.4021 (15) | C5—H5 | 0.995 |
C1—C7 | 1.4670 (14) | C6—H6 | 0.977 |
C2—C3 | 1.3899 (14) | C7—H7 | 1.010 |
C3—C4 | 1.3968 (15) | C8—H8A | 0.988 |
C4—C5 | 1.3993 (15) | C8—H8B | 0.980 |
C5—C6 | 1.3784 (13) | C10—H10 | 0.950 |
O1···C6 | 2.8906 (13) | C7···H8Biv | 3.4936 |
O2···C10 | 3.4132 (15) | C7···H10iii | 2.9850 |
C1···C4 | 2.7763 (14) | C8···H2viii | 3.5206 |
C2···C5 | 2.7778 (17) | C8···H6xiii | 3.3423 |
C3···C6 | 2.8035 (17) | C8···H8Avi | 3.4770 |
C3···C8 | 2.7953 (15) | C8···H8Bvi | 3.0613 |
O1···O2i | 3.5839 (13) | C9···H2viii | 2.9585 |
O1···C6ii | 3.3603 (15) | C9···H3vi | 3.4464 |
O1···C8i | 3.5397 (16) | C9···H6xiii | 3.2166 |
O1···C9i | 3.4739 (17) | C9···H8Avi | 3.3479 |
O1···C10iii | 3.1575 (14) | C9···H8Bvi | 2.9185 |
O2···O1i | 3.5839 (13) | C10···H2viii | 3.0407 |
O2···C1i | 3.5034 (17) | C10···H3vi | 2.9896 |
O2···C2iv | 3.5282 (16) | C10···H3viii | 3.4607 |
O2···C6i | 3.5729 (15) | C10···H5xiii | 3.5367 |
O2···C7i | 3.4779 (15) | C10···H5xiv | 3.0372 |
C1···O2i | 3.5034 (17) | C10···H6xiii | 3.5534 |
C1···C4i | 3.5512 (17) | C10···H8Bvi | 3.2660 |
C1···C5i | 3.5660 (16) | H2···O1xi | 3.5583 |
C1···C8iv | 3.5880 (18) | H2···O2v | 2.9057 |
C2···O2iv | 3.5282 (16) | H2···C7xi | 3.2950 |
C2···C5i | 3.5602 (17) | H2···C8v | 3.5206 |
C2···C10v | 3.5491 (18) | H2···C9v | 2.9585 |
C3···C4iv | 3.4949 (17) | H2···C10v | 3.0407 |
C3···C5i | 3.5907 (18) | H2···H5i | 3.5239 |
C3···C6i | 3.5640 (17) | H2···H5v | 3.5908 |
C4···C1i | 3.5512 (17) | H2···H7xi | 2.9435 |
C4···C3iv | 3.4949 (17) | H2···H10v | 3.4275 |
C4···C6i | 3.3026 (16) | H3···O1xiii | 3.4379 |
C5···C1i | 3.5660 (16) | H3···C4iv | 3.5984 |
C5···C2i | 3.5602 (17) | H3···C5iv | 3.5273 |
C5···C3i | 3.5907 (18) | H3···C9vi | 3.4464 |
C6···O1ii | 3.3603 (15) | H3···C10vi | 2.9896 |
C6···O2i | 3.5729 (15) | H3···C10v | 3.4607 |
C6···C3i | 3.5640 (17) | H3···H6i | 3.5598 |
C6···C4i | 3.3026 (16) | H3···H7xi | 3.5107 |
C7···O2i | 3.4779 (15) | H3···H10vi | 2.9257 |
C8···O1i | 3.5397 (16) | H3···H10v | 3.2297 |
C8···C1iv | 3.5880 (18) | H5···C1i | 3.5007 |
C8···C8vi | 3.5082 (17) | H5···C2i | 3.3077 |
C8···C9vi | 3.5225 (17) | H5···C3i | 3.5504 |
C9···O1i | 3.4739 (17) | H5···C7viii | 3.1921 |
C9···C8vi | 3.5225 (17) | H5···C10x | 3.5367 |
C10···O1vii | 3.1575 (14) | H5···C10xii | 3.0372 |
C10···C2viii | 3.5491 (18) | H5···H2i | 3.5239 |
O1···H6 | 2.6337 | H5···H2viii | 3.5908 |
O2···H3 | 2.6899 | H5···H7viii | 2.3799 |
O2···H5 | 2.4642 | H5···H10x | 3.4131 |
C1···H3 | 3.2914 | H5···H10xii | 2.8432 |
C1···H5 | 3.3209 | H6···O1ii | 2.4110 |
C2···H6 | 3.2988 | H6···O2i | 3.5493 |
C2···H7 | 2.5468 | H6···C3i | 3.5012 |
C3···H5 | 3.3126 | H6···C4i | 3.4439 |
C3···H8A | 2.7677 | H6···C7ii | 3.5637 |
C3···H8B | 2.6843 | H6···C8x | 3.3423 |
C4···H2 | 3.2789 | H6···C9x | 3.2166 |
C4···H6 | 3.2895 | H6···C10x | 3.5534 |
C4···H8A | 2.6337 | H6···H3i | 3.5598 |
C4···H8B | 2.5972 | H6···H6ii | 3.2783 |
C5···H3 | 3.3114 | H6···H8Ax | 2.6299 |
C6···H2 | 3.2855 | H6···H8Ai | 2.8648 |
C6···H7 | 3.3396 | H6···H8Biv | 3.2330 |
C7···H2 | 2.6135 | H6···H10xii | 3.1175 |
C7···H6 | 2.6767 | H7···O2v | 2.8373 |
C8···H3 | 2.5110 | H7···C2ix | 3.4881 |
C10···H8A | 3.1180 | H7···C4v | 3.4138 |
C10···H8B | 3.1119 | H7···C5v | 3.1133 |
H2···H3 | 2.3616 | H7···H2ix | 2.9435 |
H2···H7 | 2.3008 | H7···H3ix | 3.5107 |
H3···H8A | 2.3572 | H7···H5v | 2.3799 |
H3···H8B | 2.2315 | H7···H10iii | 3.0118 |
H5···H6 | 2.3967 | H8A···O1xiii | 2.7399 |
O1···H2ix | 3.5583 | H8A···O1i | 3.1014 |
O1···H3x | 3.4379 | H8A···C1xiii | 3.5673 |
O1···H6ii | 2.4110 | H8A···C6xiii | 3.2041 |
O1···H8Ax | 2.7399 | H8A···C6i | 3.4287 |
O1···H8Ai | 3.1014 | H8A···C7xiii | 3.3458 |
O1···H10iii | 2.2281 | H8A···C8vi | 3.4770 |
O2···H2viii | 2.9057 | H8A···C9vi | 3.3479 |
O2···H6i | 3.5493 | H8A···H6xiii | 2.6299 |
O2···H7viii | 2.8373 | H8A···H6i | 2.8648 |
C1···H5i | 3.5007 | H8A···H8Bvi | 2.9105 |
C1···H8Ax | 3.5673 | H8B···C1iv | 2.8875 |
C1···H8Biv | 2.8875 | H8B···C2iv | 3.2690 |
C2···H5i | 3.3077 | H8B···C5iv | 3.2946 |
C2···H7xi | 3.4881 | H8B···C6iv | 2.9001 |
C2···H8Biv | 3.2690 | H8B···C7iv | 3.4936 |
C3···H5i | 3.5504 | H8B···C8vi | 3.0613 |
C3···H6i | 3.5012 | H8B···C9vi | 2.9185 |
C4···H3iv | 3.5984 | H8B···C10vi | 3.2660 |
C4···H6i | 3.4439 | H8B···H6iv | 3.2330 |
C4···H7viii | 3.4138 | H8B···H8Avi | 2.9105 |
C5···H3iv | 3.5273 | H8B···H8Bvi | 2.8905 |
C5···H7viii | 3.1133 | H10···O1vii | 2.2281 |
C5···H8Biv | 3.2946 | H10···C5xiv | 3.5569 |
C5···H10xii | 3.5569 | H10···C7vii | 2.9850 |
C6···H8Ax | 3.2041 | H10···H2viii | 3.4275 |
C6···H8Ai | 3.4287 | H10···H3vi | 2.9257 |
C6···H8Biv | 2.9001 | H10···H3viii | 3.2297 |
C7···H2ix | 3.2950 | H10···H5xiii | 3.4131 |
C7···H5v | 3.1921 | H10···H5xiv | 2.8432 |
C7···H6ii | 3.5637 | H10···H6xiv | 3.1175 |
C7···H8Ax | 3.3458 | H10···H7vii | 3.0118 |
C4—O2—C8 | 116.38 (8) | C3—C2—H2 | 120.247 |
C2—C1—C6 | 119.71 (9) | C2—C3—H3 | 119.929 |
C2—C1—C7 | 119.45 (9) | C4—C3—H3 | 121.483 |
C6—C1—C7 | 120.82 (10) | C4—C5—H5 | 117.787 |
C1—C2—C3 | 121.06 (10) | C6—C5—H5 | 122.175 |
C2—C3—C4 | 118.59 (10) | C1—C6—H6 | 120.143 |
O2—C4—C3 | 124.34 (10) | C5—C6—H6 | 120.002 |
O2—C4—C5 | 114.89 (9) | O1—C7—H7 | 122.939 |
C3—C4—C5 | 120.77 (9) | C1—C7—H7 | 112.094 |
C4—C5—C6 | 120.02 (10) | O2—C8—H8A | 109.216 |
C1—C6—C5 | 119.85 (10) | O2—C8—H8B | 109.121 |
O1—C7—C1 | 124.97 (10) | C9—C8—H8A | 109.879 |
O2—C8—C9 | 108.48 (9) | C9—C8—H8B | 109.452 |
C8—C9—C10 | 177.37 (12) | H8A—C8—H8B | 110.659 |
C1—C2—H2 | 118.687 | C9—C10—H10 | 177.936 |
C4—O2—C8—C9 | −177.31 (7) | C7—C1—C6—C5 | −178.20 (9) |
C8—O2—C4—C3 | 1.73 (13) | C1—C2—C3—C4 | −0.28 (15) |
C8—O2—C4—C5 | −177.84 (8) | C2—C3—C4—O2 | −178.56 (9) |
C2—C1—C6—C5 | 0.50 (15) | C2—C3—C4—C5 | 0.99 (15) |
C6—C1—C2—C3 | −0.46 (15) | O2—C4—C5—C6 | 178.63 (8) |
C2—C1—C7—O1 | 176.92 (10) | C3—C4—C5—C6 | −0.96 (14) |
C7—C1—C2—C3 | 178.26 (9) | C4—C5—C6—C1 | 0.20 (14) |
C6—C1—C7—O1 | −4.38 (16) |
Symmetry codes: (i) −x+1, −y+1, −z+2; (ii) −x, −y+1, −z+2; (iii) x−3/2, −y+1/2, z−1/2; (iv) −x+1, −y, −z+2; (v) x−1/2, −y+1/2, z−1/2; (vi) −x+2, −y, −z+2; (vii) x+3/2, −y+1/2, z+1/2; (viii) x+1/2, −y+1/2, z+1/2; (ix) −x+1/2, y+1/2, −z+3/2; (x) x−1, y, z; (xi) −x+1/2, y−1/2, −z+3/2; (xii) −x+3/2, y+1/2, −z+5/2; (xiii) x+1, y, z; (xiv) −x+3/2, y−1/2, −z+5/2. |
D—H···A | D—H | H···A | D···A | D—H···A |
C10—H10···O1vii | 0.95 | 2.23 | 3.1575 (14) | 166 |
Symmetry code: (vii) x+3/2, −y+1/2, z+1/2. |
Experimental details
Crystal data | |
Chemical formula | C10H8O2 |
Mr | 160.17 |
Crystal system, space group | Monoclinic, P21/n |
Temperature (K) | 93 |
a, b, c (Å) | 7.906 (3), 7.385 (2), 14.036 (5) |
β (°) | 102.025 (5) |
V (Å3) | 801.5 (5) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.09 |
Crystal size (mm) | 0.20 × 0.10 × 0.10 |
Data collection | |
Diffractometer | Rigaku Saturn724+ |
Absorption correction | Numerical (NUMABS; Rigaku, 1999) |
Tmin, Tmax | 0.984, 0.991 |
No. of measured, independent and observed [F2 > 2σ(F2)] reflections | 6309, 1832, 1669 |
Rint | 0.044 |
(sin θ/λ)max (Å−1) | 0.650 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.037, 0.101, 1.06 |
No. of reflections | 1831 |
No. of parameters | 141 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.32, −0.17 |
Computer programs: CrystalClear (Rigaku, 2008), SHELXD (Schneider & Sheldrick, 2002), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 2012), CrystalStructure (Rigaku, 2010).
D—H···A | D—H | H···A | D···A | D—H···A |
C10—H10···O1i | 0.95 | 2.2281 | 3.1575 (14) | 166 |
Symmetry code: (i) x+3/2, −y+1/2, z+1/2. |
Acknowledgements
This work was supported by the Research for Promoting Technological Seeds from the Japan Science and Technology Agency (JST).
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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.
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.].