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Acta Cryst. (2008). E64, o747    [ doi:10.1107/S1600536808007496 ]

2,7-Bis(4-acetylphenoxy)naphthalene

K. Nakaema, M. Imaizumi, K. Noguchi and N. Yonezawa

Abstract top

The title compound, C26H20O4, has an asymmetrical conformation at 193 K. The 4-acetylphenyl groups are twisted away from the the naphthalene ring system, with one benzene ring turned towards the 1-position of the naphthalene ring and the other benzene ring turned towards the 6-position. The interplanar angles between the mean planes of the benzene rings and the naphthalene ring system are 68.71 (6) and 74.01 (6)°. The structure displays C-H...O hydrogen bonding and [pi]-[pi] stacking interactions [centroid-centroid and interplanar distances are 3.5938 (9) and 3.517 Å, respectively].

Comment top

An ORTEPIII (Burnett & Johnson, 1996) plot of the molecule (I) is shown in Fig. 1.Considering its two dimensional representation, the molecule could have had C2 symmetry. This is certainly not the case in practice, as the naphthalene moiety forms dihedral angles of 68.71 (6)° and 74.01 (6)° with the best mean planes of the aromatic rings C11—C16 and C19—C24, respectively. The torsion angles between the naphthalene ring and the two benzene rings are -34.0 (2)° [C11—O1—C1—C2], and -132.00 (15)° [C19—O3—C5—C4]. The difference in the two torsion angles between the naphthalene and benzene rings is rather large. This means that one benzene ring (C11—C16) turns to the 1-position, and the other benzene ring (C19—C24) turns to the 6-position rather than the 8-position. This compound has an asymmetrical conformation similar to that of 2,7-bis(3,4-dicyanophenoxy)naphthalene (Ocak et al., 2004).

The crystal packing is stabilized mainly by van der Waals interactions, however there is some π—π stacking and C—H···O intermolecular interactions (Table 1, Fig. 2). The hydrogen bonds between an acetyl hydrogen and the carbonyl oxygen of a neighboring molecule link the molecules into pairs around a center of symmetry that are aligned complementarily in a row forming a polymer-like infinitive ribbon (Fig. 2).

Related literature top

For related literature, see: Ocak et al. (2004).

Experimental top

2,7-naphthalenediol (160 mg, 1.0 mmol) and 4-fluoroacetophenone (303 mg, 2.2 mmol) were dissolved in DMF (1.0 ml) with stirring under N2. Potassium carbonate (304 mg, 2.2 mmol) was added. The reaction mixture was stirred for 24 h at 150 C° and poured into water. The products extracted with CHCl3, and washed with brine. The organic layer was dried with MgSO4 and concentrated under pressure. Slightly purplish single crystals suitable for X-ray diffraction were obtained by crystallization from ethanol.

Refinement top

All the H atoms were found in difference maps and were subsequently refined as riding atoms, with C—H = 0.95 (aromatic) and 0.98 (methyl) Å, and Uĩso~(H) = 1.2U~eq~(C).

Computing details top

Data collection: PROCESS-AUTO (Rigaku, 1998); cell refinement: PROCESS-AUTO (Rigaku, 1998); data reduction: CrystalStructure (Rigaku/MSC, 2004); program(s) used to solve structure: SIR2004 (Burla, et al., 2005); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEPIII (Burnett & Johnson, 1996); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. Molecular structure of (I), with the atom-labeling scheme and displacement ellipsoids drawn at the 50% probability level.
[Figure 2] Fig. 2. The crystal packing of the title compound, viewed down the a axis. The dashed lines indicate hydrogen bonding (blue dashed line) and π—π stacking interactions (black dashed line).
2,7-Bis(4-acetylphenoxy)naphthalene top
Crystal data top
C26H20O4Z = 2
Mr = 396.42F000 = 416
Triclinic, P1Dx = 1.363 Mg m−3
Hall symbol: -P 1Melting point = 430.2–430.9 K
a = 5.8691 (2) ÅCu Kα radiation
λ = 1.54187 Å
b = 7.9105 (2) ÅCell parameters from 12820 reflections
c = 21.4040 (5) Åθ = 4.2–68.2º
α = 90.322 (2)ºµ = 0.74 mm−1
β = 95.534 (2)ºT = 193 K
γ = 102.283 (2)ºPlatelet, clear pale purple
V = 966.11 (5) Å30.60 × 0.20 × 0.02 mm
Data collection top
Rigaku R-AXIS RAPID
diffractometer		3467 independent reflections
Radiation source: rotating anode2617 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.030
Detector resolution: 10.00 pixels mm-1θmax = 68.2º
T = 193 Kθmin = 4.2º
ω scansh = −6→6
Absorption correction: numerical
(NUMABS; Higashi, 1999)		k = −9→9
Tmin = 0.792, Tmax = 0.985l = −25→25
17040 measured reflections
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.043H-atom parameters constrained
wR(F2) = 0.125  w = 1/[σ2(Fo2) + (0.0673P)2 + 0.0881P]
where P = (Fo2 + 2Fc2)/3
S = 1.09(Δ/σ)max = 0.001
3467 reflectionsΔρmax = 0.19 e Å−3
273 parametersΔρmin = −0.24 e Å−3
Primary atom site location: structure-invariant direct methodsExtinction correction: none
Crystal data top
C26H20O4γ = 102.283 (2)º
Mr = 396.42V = 966.11 (5) Å3
Triclinic, P1Z = 2
a = 5.8691 (2) ÅCu Kα
b = 7.9105 (2) ŵ = 0.74 mm−1
c = 21.4040 (5) ÅT = 193 K
α = 90.322 (2)º0.60 × 0.20 × 0.02 mm
β = 95.534 (2)º
Data collection top
Rigaku R-AXIS RAPID
diffractometer		3467 independent reflections
Absorption correction: numerical
(NUMABS; Higashi, 1999)		2617 reflections with I > 2σ(I)
Tmin = 0.792, Tmax = 0.985Rint = 0.030
17040 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.043273 parameters
wR(F2) = 0.125H-atom parameters constrained
S = 1.09Δρmax = 0.19 e Å−3
3467 reflectionsΔρmin = −0.24 e Å−3
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
O10.4929 (2)0.04326 (15)0.14405 (5)0.0460 (3)
O20.7532 (2)0.44294 (17)−0.10302 (6)0.0578 (4)
O3−0.3337 (2)0.45641 (15)0.28446 (5)0.0445 (3)
O4−0.6274 (2)0.81543 (16)0.51905 (6)0.0542 (4)
C10.3180 (3)0.0478 (2)0.18309 (7)0.0364 (4)
C20.2243 (3)0.1895 (2)0.19006 (7)0.0363 (4)
H20.27210.28940.16610.044*
C30.0555 (3)0.18698 (19)0.23309 (6)0.0334 (4)
C4−0.0519 (3)0.3297 (2)0.24098 (7)0.0361 (4)
H4−0.01000.43080.21730.043*
C5−0.2151 (3)0.3208 (2)0.28259 (7)0.0376 (4)
C6−0.2807 (3)0.1748 (2)0.31916 (7)0.0416 (4)
H6−0.39390.17240.34820.050*
C7−0.1796 (3)0.0366 (2)0.31236 (7)0.0402 (4)
H7−0.2233−0.06220.33710.048*
C8−0.0113 (3)0.03715 (19)0.26930 (6)0.0344 (4)
C90.0924 (3)−0.1059 (2)0.26025 (7)0.0410 (4)
H90.0496−0.20650.28410.049*
C100.2526 (3)−0.1022 (2)0.21793 (7)0.0407 (4)
H100.3194−0.19970.21200.049*
C110.4961 (3)0.13361 (19)0.08868 (7)0.0361 (4)
C120.2975 (3)0.1256 (2)0.04757 (7)0.0402 (4)
H120.14890.06640.05860.048*
C130.3166 (3)0.2042 (2)−0.00971 (7)0.0395 (4)
H130.18000.1984−0.03800.047*
C140.5327 (3)0.29172 (18)−0.02654 (7)0.0341 (4)
C150.7292 (3)0.3012 (2)0.01629 (7)0.0393 (4)
H150.87770.36230.00590.047*
C160.7120 (3)0.2230 (2)0.07376 (7)0.0392 (4)
H160.84730.23070.10270.047*
C170.5597 (3)0.3703 (2)−0.08936 (7)0.0403 (4)
C180.3482 (3)0.3545 (2)−0.13569 (8)0.0510 (5)
H18A0.39250.4167−0.17360.061*
H18B0.23010.4043−0.11720.061*
H18C0.28350.2321−0.14660.061*
C19−0.3525 (3)0.52941 (19)0.34179 (7)0.0359 (4)
C20−0.1817 (3)0.5418 (2)0.39204 (7)0.0404 (4)
H20−0.05020.49100.38910.049*
C21−0.2046 (3)0.6289 (2)0.44668 (7)0.0409 (4)
H21−0.08590.63980.48080.049*
C22−0.3988 (3)0.70055 (19)0.45228 (7)0.0359 (4)
C23−0.5678 (3)0.6862 (2)0.40098 (7)0.0408 (4)
H23−0.70100.73510.40390.049*
C24−0.5448 (3)0.6021 (2)0.34601 (7)0.0398 (4)
H24−0.66060.59420.31130.048*
C25−0.4346 (3)0.7891 (2)0.51118 (7)0.0407 (4)
C26−0.2330 (3)0.8422 (3)0.56052 (8)0.0545 (5)
H26A−0.26490.93130.58840.065*
H26B−0.09020.88850.54050.065*
H26C−0.21170.74150.58510.065*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0475 (7)0.0581 (7)0.0407 (6)0.0246 (6)0.0160 (5)0.0149 (5)
O20.0560 (8)0.0639 (8)0.0516 (7)0.0043 (6)0.0144 (6)0.0169 (6)
O30.0530 (7)0.0528 (7)0.0338 (6)0.0234 (6)0.0082 (5)0.0020 (5)
O40.0503 (8)0.0594 (8)0.0558 (7)0.0128 (6)0.0184 (6)−0.0041 (6)
C10.0351 (9)0.0458 (9)0.0299 (8)0.0113 (7)0.0054 (6)0.0031 (6)
C20.0380 (9)0.0388 (9)0.0315 (8)0.0067 (7)0.0041 (6)0.0051 (6)
C30.0338 (8)0.0389 (8)0.0266 (7)0.0062 (7)0.0010 (6)0.0007 (6)
C40.0395 (9)0.0370 (8)0.0311 (8)0.0064 (7)0.0038 (6)0.0030 (6)
C50.0385 (9)0.0427 (9)0.0332 (8)0.0127 (7)0.0025 (6)−0.0026 (6)
C60.0407 (10)0.0492 (10)0.0352 (8)0.0070 (8)0.0117 (7)0.0014 (7)
C70.0418 (10)0.0405 (9)0.0364 (8)0.0029 (7)0.0073 (7)0.0050 (7)
C80.0338 (9)0.0388 (8)0.0294 (7)0.0054 (7)0.0024 (6)0.0014 (6)
C90.0466 (10)0.0372 (9)0.0383 (8)0.0063 (7)0.0058 (7)0.0059 (7)
C100.0464 (10)0.0401 (9)0.0386 (9)0.0151 (7)0.0063 (7)0.0032 (7)
C110.0411 (9)0.0378 (8)0.0328 (8)0.0136 (7)0.0087 (7)0.0033 (6)
C120.0335 (9)0.0448 (9)0.0413 (9)0.0034 (7)0.0099 (7)0.0014 (7)
C130.0352 (9)0.0461 (9)0.0363 (8)0.0075 (7)0.0021 (7)−0.0014 (7)
C140.0375 (9)0.0310 (8)0.0349 (8)0.0085 (6)0.0064 (6)−0.0014 (6)
C150.0339 (9)0.0390 (9)0.0438 (9)0.0031 (7)0.0085 (7)0.0023 (7)
C160.0341 (9)0.0466 (9)0.0375 (8)0.0106 (7)0.0025 (7)0.0004 (7)
C170.0483 (10)0.0364 (8)0.0390 (9)0.0126 (7)0.0103 (7)0.0020 (7)
C180.0608 (12)0.0583 (11)0.0380 (9)0.0221 (9)0.0049 (8)0.0060 (8)
C190.0377 (9)0.0370 (8)0.0346 (8)0.0083 (7)0.0103 (7)0.0032 (6)
C200.0353 (9)0.0462 (9)0.0426 (9)0.0143 (7)0.0053 (7)0.0019 (7)
C210.0388 (9)0.0459 (9)0.0390 (9)0.0123 (7)0.0019 (7)0.0027 (7)
C220.0358 (9)0.0335 (8)0.0383 (8)0.0053 (6)0.0079 (7)0.0031 (6)
C230.0332 (9)0.0433 (9)0.0478 (9)0.0103 (7)0.0081 (7)0.0022 (7)
C240.0345 (9)0.0446 (9)0.0411 (9)0.0110 (7)0.0020 (7)0.0016 (7)
C250.0445 (10)0.0369 (8)0.0418 (9)0.0073 (7)0.0129 (7)0.0054 (7)
C260.0574 (12)0.0635 (12)0.0432 (10)0.0149 (9)0.0048 (8)−0.0075 (8)
Geometric parameters (Å, °) top
O1—C111.3871 (17)C13—C141.391 (2)
O1—C11.3905 (17)C13—H130.9500
O2—C171.2225 (18)C14—C151.391 (2)
O3—C191.3772 (17)C14—C171.492 (2)
O3—C51.4001 (18)C15—C161.383 (2)
O4—C251.2201 (19)C15—H150.9500
C1—C21.363 (2)C16—H160.9500
C1—C101.408 (2)C17—C181.495 (2)
C2—C31.413 (2)C18—H18A0.9800
C2—H20.9500C18—H18B0.9800
C3—C41.422 (2)C18—H18C0.9800
C3—C81.425 (2)C19—C241.381 (2)
C4—C51.361 (2)C19—C201.386 (2)
C4—H40.9500C20—C211.386 (2)
C5—C61.405 (2)C20—H200.9500
C6—C71.363 (2)C21—C221.391 (2)
C6—H60.9500C21—H210.9500
C7—C81.414 (2)C22—C231.394 (2)
C7—H70.9500C22—C251.493 (2)
C8—C91.415 (2)C23—C241.381 (2)
C9—C101.363 (2)C23—H230.9500
C9—H90.9500C24—H240.9500
C10—H100.9500C25—C261.495 (2)
C11—C161.381 (2)C26—H26A0.9800
C11—C121.381 (2)C26—H26B0.9800
C12—C131.381 (2)C26—H26C0.9800
C12—H120.9500
C11—O1—C1119.52 (12)C13—C14—C17122.02 (14)
C19—O3—C5118.88 (11)C16—C15—C14121.10 (14)
C2—C1—O1123.00 (14)C16—C15—H15119.5
C2—C1—C10121.89 (14)C14—C15—H15119.5
O1—C1—C10115.03 (14)C11—C16—C15119.34 (15)
C1—C2—C3119.57 (14)C11—C16—H16120.3
C1—C2—H2120.2C15—C16—H16120.3
C3—C2—H2120.2O2—C17—C14120.20 (15)
C2—C3—C4121.79 (14)O2—C17—C18120.69 (14)
C2—C3—C8119.44 (14)C14—C17—C18119.09 (14)
C4—C3—C8118.76 (13)C17—C18—H18A109.5
C5—C4—C3119.74 (14)C17—C18—H18B109.5
C5—C4—H4120.1H18A—C18—H18B109.5
C3—C4—H4120.1C17—C18—H18C109.5
C4—C5—O3117.97 (14)H18A—C18—H18C109.5
C4—C5—C6122.15 (15)H18B—C18—H18C109.5
O3—C5—C6119.65 (14)O3—C19—C24116.52 (14)
C7—C6—C5119.04 (14)O3—C19—C20122.80 (14)
C7—C6—H6120.5C24—C19—C20120.53 (14)
C5—C6—H6120.5C19—C20—C21119.39 (15)
C6—C7—C8121.46 (14)C19—C20—H20120.3
C6—C7—H7119.3C21—C20—H20120.3
C8—C7—H7119.3C20—C21—C22121.00 (15)
C7—C8—C9122.66 (14)C20—C21—H21119.5
C7—C8—C3118.84 (14)C22—C21—H21119.5
C9—C8—C3118.50 (14)C21—C22—C23118.36 (14)
C10—C9—C8121.31 (14)C21—C22—C25122.64 (15)
C10—C9—H9119.3C23—C22—C25118.98 (14)
C8—C9—H9119.3C24—C23—C22121.06 (15)
C9—C10—C1119.28 (15)C24—C23—H23119.5
C9—C10—H10120.4C22—C23—H23119.5
C1—C10—H10120.4C23—C24—C19119.63 (15)
C16—C11—C12120.70 (14)C23—C24—H24120.2
C16—C11—O1116.81 (14)C19—C24—H24120.2
C12—C11—O1122.32 (14)O4—C25—C22120.09 (15)
C11—C12—C13119.49 (14)O4—C25—C26120.68 (15)
C11—C12—H12120.3C22—C25—C26119.22 (14)
C13—C12—H12120.3C25—C26—H26A109.5
C12—C13—C14121.00 (15)C25—C26—H26B109.5
C12—C13—H13119.5H26A—C26—H26B109.5
C14—C13—H13119.5C25—C26—H26C109.5
C15—C14—C13118.34 (14)H26A—C26—H26C109.5
C15—C14—C17119.62 (14)H26B—C26—H26C109.5
C11—O1—C1—C2−34.0 (2)O1—C11—C12—C13−173.43 (14)
C11—O1—C1—C10149.36 (14)C11—C12—C13—C14−0.2 (2)
O1—C1—C2—C3−176.78 (13)C12—C13—C14—C15−1.2 (2)
C10—C1—C2—C3−0.4 (2)C12—C13—C14—C17176.96 (14)
C1—C2—C3—C4−178.38 (14)C13—C14—C15—C161.2 (2)
C1—C2—C3—C81.0 (2)C17—C14—C15—C16−177.04 (14)
C2—C3—C4—C5179.42 (14)C12—C11—C16—C15−1.7 (2)
C8—C3—C4—C50.0 (2)O1—C11—C16—C15173.65 (13)
C3—C4—C5—O3−173.71 (12)C14—C15—C16—C110.3 (2)
C3—C4—C5—C60.7 (2)C15—C14—C17—O2−0.2 (2)
C19—O3—C5—C4−132.00 (15)C13—C14—C17—O2−178.38 (14)
C19—O3—C5—C653.40 (19)C15—C14—C17—C18178.13 (14)
C4—C5—C6—C7−0.7 (2)C13—C14—C17—C180.0 (2)
O3—C5—C6—C7173.69 (14)C5—O3—C19—C24−152.32 (14)
C5—C6—C7—C8−0.2 (2)C5—O3—C19—C2032.1 (2)
C6—C7—C8—C9−178.51 (14)O3—C19—C20—C21175.05 (14)
C6—C7—C8—C30.9 (2)C24—C19—C20—C21−0.4 (2)
C2—C3—C8—C7179.76 (13)C19—C20—C21—C221.4 (2)
C4—C3—C8—C7−0.8 (2)C20—C21—C22—C23−1.5 (2)
C2—C3—C8—C9−0.8 (2)C20—C21—C22—C25177.50 (14)
C4—C3—C8—C9178.62 (13)C21—C22—C23—C240.4 (2)
C7—C8—C9—C10179.34 (14)C25—C22—C23—C24−178.56 (14)
C3—C8—C9—C10−0.1 (2)C22—C23—C24—C190.6 (2)
C8—C9—C10—C10.7 (2)O3—C19—C24—C23−176.32 (13)
C2—C1—C10—C9−0.5 (2)C20—C19—C24—C23−0.6 (2)
O1—C1—C10—C9176.16 (13)C21—C22—C25—O4−163.64 (15)
C1—O1—C11—C16137.94 (14)C23—C22—C25—O415.3 (2)
C1—O1—C11—C12−46.8 (2)C21—C22—C25—C2615.4 (2)
C16—C11—C12—C131.7 (2)C23—C22—C25—C26−165.70 (15)
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
C2—H2···O2i0.952.543.448 (2)160
Symmetry codes: (i) −x+1, −y+1, −z.
Table 1
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
C2—H2···O2i0.952.543.448 (2)160
Symmetry codes: (i) −x+1, −y+1, −z.
Acknowledgements top

This work was partially supported by the Ogasawara Foundation for the Promotion of Science & Engineering, Tokyo, Japan.

references
References top

Burla, M. C., Caliandro, R., Camalli, M., Carrozzini, B., Cascarano, G. L., De Caro, L., Giacovazzo, C., Polidori, G. & Spagna, R. (2005). J. Appl. Cryst. 38, 381–388.

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