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Acta Crystallogr Sect E Struct Rep Online. 2008 December 1; 64(Pt 12): o2383.
Published online 2008 November 20. doi:  10.1107/S1600536808037549
PMCID: PMC2960027

2,3-Bis(prop-2-yn­yloxy)naphthalene

Abstract

In the crystal structure of the title compound, C16H12O2, no classical hydrogen bonds or aromatic π–π stacking inter­actions were observed. The mol­ecules are linked into a three-dimensional framework by a combination of C—H(...)O and C—H(...)π(arene) hydrogen bonds.

Related literature

For related structures, see: Zhang et al. (2008 [triangle]); Ghosh et al. (2007 [triangle]); Wang & Kong (2007 [triangle]). For the synthesis, see: Burchell et al. (2006 [triangle]). For bond-length data, see: Allen et al. (1987 [triangle]). For π–π stacking inter­actions, see: Steed & Atwood (2000 [triangle]).

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Object name is e-64-o2383-scheme1.jpg

Experimental

Crystal data

  • C16H12O2
  • M r = 236.26
  • Orthorhombic, An external file that holds a picture, illustration, etc.
Object name is e-64-o2383-efi1.jpg
  • a = 8.2921 (12) Å
  • b = 9.0457 (14) Å
  • c = 33.070 (5) Å
  • V = 2480.5 (6) Å3
  • Z = 8
  • Mo Kα radiation
  • μ = 0.08 mm−1
  • T = 298 (2) K
  • 0.18 × 0.16 × 0.15 mm

Data collection

  • Bruker SMART APEXII CCD area-detector diffractometer
  • Absorption correction: multi-scan (SADABS; Bruker, 2005 [triangle]) T min = 0.984, T max = 0.989
  • 12468 measured reflections
  • 2182 independent reflections
  • 1782 reflections with I > 2σ(I)
  • R int = 0.033

Refinement

  • R[F 2 > 2σ(F 2)] = 0.039
  • wR(F 2) = 0.101
  • S = 1.04
  • 2182 reflections
  • 163 parameters
  • H-atom parameters constrained
  • Δρmax = 0.17 e Å−3
  • Δρmin = −0.19 e Å−3

Data collection: APEX2 (Bruker, 2005 [triangle]); cell refinement: APEX2; data reduction: SAINT (Bruker, 2005 [triangle]); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: SHELXTL (Sheldrick, 2008 [triangle]); software used to prepare material for publication: SHELXTL.

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808037549/bv2111sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808037549/bv2111Isup2.hkl

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

Acknowledgments

The authors are grateful for financial support from the Henan Administration of Science and Technology (grant No. 0111030700).

supplementary crystallographic information

Comment

The title compound has been characterized by X–ray methods (Fig. 1). The bond lengths and angles are within normal ranges (Allen et al. 1987). Except for an ethinyl groug [–C15[equivalent]C16–H16], all the remaining non–H atoms are almost coplanar, with a mean deviation from the least-square plane to be 0.0402 (14) Å. The angle between the ethinyl and the plane is 23.80 (9)°.

While π—π stacking interactions are often found in aromatics (Wang et al. 2007), in the title complex the minimal distance between ring centroids is 5.188 (1) Å indicating that there are no π—π stacking interactions present(Steed et al. 2000).

The molecules of the title complex are linked into a three-dimensional framework by a combination of C—H···O and C—H···π (arene) hydrogen bonds (Fig. 2, Fig. 3, Table 1). [Cg1 id the centroid of the C4–C6/C11–C13 ring. Symmetry codes: (i) -x, y + 1/2, -z + 1/2; (ii) -x - 1/2, y - 1/2, z + 2.]

Experimental

The title compound was obtained unintentionally during an attempted synthesis of a network complex (Burchell et al., 2006) based on Co(II) and 2,3-bis(prop-2-ynyloxy)naphthalene, involving the evaporation of a methyl alchol and acetone solution of CoCl~2~, NaN~3~ and the title molecule, at 298 K.

Refinement

All the H atoms could be detected in the difference electron density maps. Nevertheless, they were situated into the idealized position and refined using a riding model. C—H = 0.97 Å for the methylene groups and C—H = 0.93 Å for the remaining H atoms. Uiso(H) = 1.2 Ueq (carrier C) for all the H atoms.

Figures

Fig. 1.
A view of the title compound, showing the atom-labeling scheme. Displacement ellipsoids are drawn at the 50% probability level and H atoms are shown as small spheres of arbritary radii.
Fig. 2.
The three-dimensional supramolecular framework of the title complound formed by C—H···O and C—H···π (arene) hydrogen bonds, viewed along the a axis.
Fig. 3.
The three-dimensional supramolecular framework of the title complound formed by C—H···O and C—H···π (arene) hydrogen bonds, viewed along the b axis.

Crystal data

C16H12O2F000 = 992
Mr = 236.26Dx = 1.265 Mg m3
Orthorhombic, PbcaMo Kα radiation λ = 0.71073 Å
Hall symbol: -P 2ac 2abCell parameters from 3821 reflections
a = 8.2921 (12) Åθ = 2.8–25.7º
b = 9.0457 (14) ŵ = 0.08 mm1
c = 33.070 (5) ÅT = 298 (2) K
V = 2480.5 (6) Å3Block, colourless
Z = 80.18 × 0.16 × 0.15 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer2182 independent reflections
Radiation source: fine-focus sealed tube1782 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.033
T = 298(2) Kθmax = 25.0º
ω scansθmin = 2.5º
Absorption correction: multi-scan(SADABS; Bruker, 2005)h = −9→9
Tmin = 0.984, Tmax = 0.989k = −10→10
12468 measured reflectionsl = −39→29

Refinement

Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.039H-atom parameters constrained
wR(F2) = 0.101  w = 1/[σ2(Fo2) + (0.0527P)2 + 0.338P] where P = (Fo2 + 2Fc2)/3
S = 1.04(Δ/σ)max < 0.001
2182 reflectionsΔρmax = 0.17 e Å3
163 parametersΔρmin = −0.19 e Å3
Primary atom site location: structure-invariant direct methodsExtinction correction: none

Special details

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)

xyzUiso*/Ueq
C1−0.1360 (2)−0.0848 (2)0.32753 (6)0.0752 (6)
H1−0.1425−0.16720.31080.090*
C2−0.1277 (2)0.01867 (18)0.34856 (5)0.0574 (4)
C3−0.1181 (2)0.14633 (16)0.37505 (5)0.0554 (4)
H3A−0.22490.18650.37980.066*
H3B−0.07200.11820.40090.066*
C40.00170 (15)0.38601 (15)0.37523 (4)0.0400 (3)
C5−0.05860 (17)0.42250 (16)0.41224 (4)0.0462 (4)
H5−0.11820.35320.42670.055*
C6−0.03174 (17)0.56457 (16)0.42903 (4)0.0451 (4)
C7−0.0984 (2)0.60874 (19)0.46649 (4)0.0586 (4)
H7−0.16090.54220.48110.070*
C8−0.0727 (3)0.7468 (2)0.48143 (5)0.0703 (5)
H8−0.11820.77410.50600.084*
C90.0218 (2)0.8480 (2)0.45997 (5)0.0696 (5)
H90.04010.94170.47060.084*
C100.0875 (2)0.80997 (18)0.42353 (5)0.0577 (4)
H100.15000.87820.40950.069*
C110.06147 (17)0.66812 (16)0.40699 (4)0.0443 (3)
C120.12274 (17)0.62803 (15)0.36856 (4)0.0436 (3)
H120.18300.69590.35380.052*
C130.09452 (16)0.49128 (15)0.35298 (4)0.0391 (3)
C140.24207 (18)0.53826 (15)0.29190 (4)0.0447 (3)
H14A0.30800.48090.27350.054*
H14B0.31390.59470.30920.054*
C150.14206 (18)0.64031 (16)0.26860 (4)0.0448 (4)
C160.0667 (2)0.71916 (18)0.24743 (5)0.0575 (4)
H160.00730.78140.23070.069*
O1−0.01832 (12)0.25415 (10)0.35571 (3)0.0479 (3)
O20.14871 (12)0.43928 (10)0.31646 (3)0.0471 (3)

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
C10.0882 (14)0.0598 (11)0.0778 (12)−0.0163 (10)0.0254 (11)−0.0032 (10)
C20.0584 (10)0.0467 (9)0.0672 (10)−0.0065 (7)0.0180 (8)0.0088 (8)
C30.0586 (10)0.0444 (8)0.0631 (9)−0.0032 (7)0.0164 (8)0.0104 (7)
C40.0354 (7)0.0398 (7)0.0448 (8)0.0031 (6)0.0005 (6)0.0047 (6)
C50.0454 (8)0.0499 (8)0.0433 (8)0.0030 (7)0.0040 (6)0.0117 (7)
C60.0448 (8)0.0544 (9)0.0361 (7)0.0091 (7)−0.0050 (6)0.0042 (6)
C70.0660 (10)0.0696 (11)0.0403 (8)0.0089 (8)0.0054 (8)0.0055 (8)
C80.0896 (14)0.0803 (13)0.0410 (8)0.0154 (11)0.0053 (9)−0.0092 (8)
C90.0884 (13)0.0660 (11)0.0545 (10)0.0014 (10)−0.0006 (9)−0.0156 (9)
C100.0643 (10)0.0572 (9)0.0517 (9)−0.0036 (8)−0.0007 (8)−0.0081 (7)
C110.0418 (8)0.0508 (8)0.0403 (7)0.0042 (6)−0.0051 (6)−0.0007 (6)
C120.0418 (8)0.0453 (8)0.0438 (8)−0.0042 (6)0.0031 (6)0.0029 (6)
C130.0345 (7)0.0440 (7)0.0388 (7)0.0025 (6)0.0021 (6)0.0022 (6)
C140.0452 (8)0.0438 (7)0.0453 (7)−0.0025 (6)0.0115 (7)0.0018 (6)
C150.0497 (8)0.0442 (8)0.0405 (7)−0.0073 (7)0.0029 (7)−0.0073 (6)
C160.0616 (10)0.0558 (9)0.0552 (9)−0.0044 (8)−0.0124 (8)0.0009 (8)
O10.0499 (6)0.0404 (5)0.0535 (6)−0.0050 (4)0.0135 (5)0.0027 (4)
O20.0535 (6)0.0423 (5)0.0454 (5)−0.0060 (5)0.0140 (5)−0.0010 (4)

Geometric parameters (Å, °)

C1—C21.168 (2)C8—H80.9300
C1—H10.9300C9—C101.367 (2)
C2—C31.452 (2)C9—H90.9300
C3—O11.4299 (16)C10—C111.412 (2)
C3—H3A0.9700C10—H100.9300
C3—H3B0.9700C11—C121.416 (2)
C4—C51.363 (2)C12—C131.3603 (19)
C4—O11.3663 (16)C12—H120.9300
C4—C131.4285 (18)C13—O21.3718 (15)
C5—C61.418 (2)C14—O21.4354 (16)
C5—H50.9300C14—C151.461 (2)
C6—C71.414 (2)C14—H14A0.9700
C6—C111.416 (2)C14—H14B0.9700
C7—C81.360 (2)C15—C161.179 (2)
C7—H70.9300C16—H160.9300
C8—C91.399 (3)
C2—C1—H1180.0C10—C9—H9119.8
C1—C2—C3179.39 (17)C8—C9—H9119.8
O1—C3—C2107.72 (12)C9—C10—C11120.64 (16)
O1—C3—H3A110.2C9—C10—H10119.7
C2—C3—H3A110.2C11—C10—H10119.7
O1—C3—H3B110.2C10—C11—C12121.72 (14)
C2—C3—H3B110.2C10—C11—C6119.03 (13)
H3A—C3—H3B108.5C12—C11—C6119.23 (13)
C5—C4—O1126.24 (12)C13—C12—C11120.74 (13)
C5—C4—C13119.93 (13)C13—C12—H12119.6
O1—C4—C13113.83 (11)C11—C12—H12119.6
C4—C5—C6120.91 (13)C12—C13—O2126.08 (12)
C4—C5—H5119.5C12—C13—C4120.25 (12)
C6—C5—H5119.5O2—C13—C4113.67 (11)
C7—C6—C11118.51 (14)O2—C14—C15112.73 (12)
C7—C6—C5122.53 (14)O2—C14—H14A109.0
C11—C6—C5118.93 (12)C15—C14—H14A109.0
C8—C7—C6121.10 (16)O2—C14—H14B109.0
C8—C7—H7119.4C15—C14—H14B109.0
C6—C7—H7119.4H14A—C14—H14B107.8
C7—C8—C9120.29 (16)C16—C15—C14175.37 (15)
C7—C8—H8119.9C15—C16—H16180.0
C9—C8—H8119.9C4—O1—C3117.03 (11)
C10—C9—C8120.41 (17)C13—O2—C14117.45 (10)
O1—C4—C5—C6−178.85 (12)C10—C11—C12—C13−179.18 (14)
C13—C4—C5—C60.5 (2)C6—C11—C12—C13−0.7 (2)
C4—C5—C6—C7177.07 (13)C11—C12—C13—O2−179.26 (12)
C4—C5—C6—C11−1.0 (2)C11—C12—C13—C40.2 (2)
C11—C6—C7—C8−0.7 (2)C5—C4—C13—C12−0.1 (2)
C5—C6—C7—C8−178.81 (15)O1—C4—C13—C12179.33 (12)
C6—C7—C8—C9−0.5 (3)C5—C4—C13—O2179.43 (12)
C7—C8—C9—C100.9 (3)O1—C4—C13—O2−1.12 (16)
C8—C9—C10—C11−0.2 (3)C5—C4—O1—C33.1 (2)
C9—C10—C11—C12177.43 (15)C13—C4—O1—C3−176.35 (12)
C9—C10—C11—C6−1.0 (2)C2—C3—O1—C4177.75 (12)
C7—C6—C11—C101.4 (2)C12—C13—O2—C14−1.0 (2)
C5—C6—C11—C10179.60 (13)C4—C13—O2—C14179.51 (11)
C7—C6—C11—C12−177.05 (13)C15—C14—O2—C13−81.84 (15)
C5—C6—C11—C121.1 (2)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
C16—H16···O2i0.932.483.409 (2)177
C3—H3A···Cg1ii0.972.953.634 (2)129

Symmetry codes: (i) −x, y+1/2, −z+1/2; (ii) −x−1/2, y−1/2, z.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BV2111).

References

  • Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1–19.
  • Bruker (2005). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
  • Burchell, T. J., Jennings, M. C. & Puddephatt, R. J. (2006). Inorg. Chim. Acta, 359, 2812–2818.
  • Ghosh, S., Mukhopadhyay, R., Helliwell, M. & Mukherjee, A. K. (2007). Acta Cryst. C63, o496–o500. [PubMed]
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Steed, J. W. & Atwood, J. L. (2000). Supramolecular Chemistry, p. 26. Chichester: John Wiley & Sons.
  • Wang, X.-B. & Kong, L.-Y. (2007). Acta Cryst. E63, o4340.
  • Zhang, W., Cui, Q. & Yu, Z. (2008). Acta Cryst. E64, o317. [PMC free article] [PubMed]

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