PMCCPMCCPMCC

Search tips
Search criteria 

Advanced

 
Logo of actaeInternational Union of Crystallographysearchopen accessarticle submissionjournal home pagethis article
 
Acta Crystallogr Sect E Struct Rep Online. 2010 July 1; 66(Pt 7): o1610.
Published online 2010 June 9. doi:  10.1107/S1600536810020982
PMCID: PMC3006840

2,7-Bis(prop-2-yn-1-yl­oxy)naphthalene

Abstract

The title compound, C16H12O2, was synthesized from naphthalene-2,7-diol and prop-2-ynyl 4-methyl­benzene­sulfonate in the presence of sodium hydride. The crystal packing exhibits inter­molecular non-classical C—H(...)O hydrogen bonds and C—H(...)π inter­actions.

Related literature

For the preparation of the title compound, see: Srinivasan et al. (2006 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-66-o1610-scheme1.jpg

Experimental

Crystal data

  • C16H12O2
  • M r = 236.26
  • Orthorhombic, An external file that holds a picture, illustration, etc.
Object name is e-66-o1610-efi1.jpg
  • a = 11.3742 (12) Å
  • b = 8.1364 (9) Å
  • c = 26.880 (3) Å
  • V = 2487.6 (5) Å3
  • Z = 8
  • Mo Kα radiation
  • μ = 0.08 mm−1
  • T = 298 K
  • 0.16 × 0.12 × 0.04 mm

Data collection

  • Bruker SMART 1000 diffractometer
  • 8492 measured reflections
  • 2812 independent reflections
  • 1807 reflections with I > 2σ(I)
  • R int = 0.070

Refinement

  • R[F 2 > 2σ(F 2)] = 0.063
  • wR(F 2) = 0.146
  • S = 1.02
  • 2812 reflections
  • 163 parameters
  • H-atom parameters constrained
  • Δρmax = 0.17 e Å−3
  • Δρmin = −0.23 e Å−3

Data collection: SMART (Bruker, 1999 [triangle]); cell refinement: SAINT (Bruker, 1999 [triangle]); data reduction: SAINT; 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/S1600536810020982/om2339sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810020982/om2339Isup2.hkl

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

Acknowledgments

The authors are grateful to Xianggao Meng for the data collection.

supplementary crystallographic information

Comment

Naphthalene derivatives have manifested applications in many fields, for example, as a colorant, explosive, disinfectant, insecticide and plant hormone auxin. The reaction which between hydroxybenzene and prop-2-yn-1-yl 4-methylbenzenesulfonate gives rise to the product with rapid reaction rates by the introduction of sodium hydride (Srinivasan et al., 2006;).

Here we report the crystal structure of the title compound (Fig. 1). The crystal packing exhibits non-classical C—H···O hydrogen bonds and C—H···π interaction (Table 1).

Experimental

The title compound was synthesized according to the literature procedure of Srinivasan et al. (2006). Single crystals suitable for X-ray diffraction were prepared by slow evaporation of a solution of the title compound in chloroform : methanol (10:1) at room temperature.

Refinement

All H atoms were initially located in a difference map, but were constrained to an idealized geometry. Constrained bond lengths and isotropic displacement parameters: (C—H = 0.97 Å) and Uiso(H) = 1.2 Ueq(C) for methylene, (C—H = 0.93 Å) and Uiso(H) =1.2Ueq(C) for aromatic H atoms, and (C—H = 0.93 Å) and Uiso(H) = 1.2Ueq(C) for alkynyl aromatic H atoms.

Figures

Fig. 1.
View of the title compound showing the atom-labelling scheme. Displacement ellipsoids are drawn at the 30% probability level. H atoms are represented by spheres of arbitrary radius.

Crystal data

C16H12O2F(000) = 992
Mr = 236.26Dx = 1.262 Mg m3
Orthorhombic, PbcaMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2abCell parameters from 1273 reflections
a = 11.3742 (12) Åθ = 3.0–22.2°
b = 8.1364 (9) ŵ = 0.08 mm1
c = 26.880 (3) ÅT = 298 K
V = 2487.6 (5) Å3Plate, colorless
Z = 80.16 × 0.12 × 0.04 mm

Data collection

Bruker SMART 1000 diffractometer1807 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.070
graphiteθmax = 27.5°, θmin = 2.4°
[var phi] and ω scansh = −14→12
8492 measured reflectionsk = −9→10
2812 independent reflectionsl = −11→34

Refinement

Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.063Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.146H-atom parameters constrained
S = 1.02w = 1/[σ2(Fo2) + (0.0571P)2] where P = (Fo2 + 2Fc2)/3
2812 reflections(Δ/σ)max = 0.001
163 parametersΔρmax = 0.17 e Å3
0 restraintsΔρmin = −0.23 e Å3

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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
C10.88182 (18)0.2124 (2)0.28194 (7)0.0385 (5)
C20.78099 (18)0.1252 (3)0.26709 (8)0.0441 (5)
H20.72960.08390.29090.053*
C30.75854 (19)0.1013 (3)0.21809 (8)0.0462 (6)
H30.69150.04370.20870.055*
C40.83522 (18)0.1623 (2)0.18105 (7)0.0373 (5)
C50.8135 (2)0.1425 (3)0.12958 (8)0.0479 (6)
H50.74580.08810.11920.057*
C60.8896 (2)0.2014 (3)0.09503 (8)0.0486 (6)
H60.87330.18790.06140.058*
C70.99257 (19)0.2824 (2)0.10979 (7)0.0410 (5)
C81.01698 (18)0.3049 (2)0.15926 (7)0.0386 (5)
H81.08570.35840.16880.046*
C90.93755 (18)0.2466 (2)0.19607 (7)0.0349 (5)
C100.95915 (17)0.2723 (2)0.24742 (7)0.0356 (5)
H101.02560.32960.25760.043*
C110.9945 (2)0.3094 (3)0.35131 (8)0.0511 (6)
H11A0.98760.42700.34600.061*
H11B1.06420.27070.33420.061*
C121.0032 (2)0.2742 (3)0.40422 (8)0.0538 (6)
C131.0111 (2)0.2413 (3)0.44607 (10)0.0777 (9)
H131.01730.21490.47960.093*
C141.1715 (2)0.4069 (3)0.08303 (7)0.0486 (6)
H14A1.22480.32550.09670.058*
H14B1.16020.49260.10770.058*
C151.2208 (2)0.4766 (3)0.03774 (8)0.0512 (6)
C161.2596 (2)0.5391 (3)0.00261 (10)0.0727 (8)
H161.29070.5892−0.02560.087*
O10.89297 (13)0.22760 (17)0.33268 (5)0.0490 (4)
O21.06171 (14)0.33243 (19)0.07121 (5)0.0513 (4)

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
C10.0421 (13)0.0378 (11)0.0356 (11)0.0007 (10)−0.0013 (9)0.0027 (9)
C20.0396 (13)0.0481 (13)0.0448 (13)−0.0091 (10)0.0048 (10)0.0058 (10)
C30.0381 (13)0.0467 (13)0.0540 (14)−0.0078 (10)−0.0041 (10)−0.0019 (11)
C40.0371 (13)0.0350 (11)0.0398 (11)0.0014 (9)−0.0048 (9)−0.0021 (9)
C50.0450 (14)0.0507 (13)0.0479 (13)−0.0044 (11)−0.0123 (11)−0.0066 (11)
C60.0592 (16)0.0554 (14)0.0312 (11)0.0003 (12)−0.0104 (10)−0.0058 (10)
C70.0487 (14)0.0408 (12)0.0335 (11)0.0012 (10)−0.0006 (10)−0.0022 (9)
C80.0406 (13)0.0422 (12)0.0329 (11)−0.0031 (10)−0.0035 (9)−0.0013 (9)
C90.0390 (12)0.0324 (10)0.0331 (10)0.0024 (9)−0.0026 (9)−0.0015 (8)
C100.0357 (12)0.0377 (11)0.0333 (10)−0.0018 (9)−0.0032 (8)0.0012 (8)
C110.0502 (15)0.0653 (15)0.0377 (12)−0.0113 (12)0.0010 (10)0.0041 (10)
C120.0550 (16)0.0705 (16)0.0358 (12)−0.0158 (13)0.0011 (11)−0.0001 (11)
C130.078 (2)0.119 (2)0.0368 (14)−0.0317 (17)−0.0031 (13)0.0089 (14)
C140.0537 (15)0.0559 (14)0.0361 (11)−0.0011 (12)0.0023 (10)−0.0015 (10)
C150.0618 (16)0.0499 (14)0.0420 (13)0.0013 (12)0.0130 (11)−0.0047 (11)
C160.092 (2)0.0675 (17)0.0582 (17)−0.0010 (15)0.0295 (15)0.0021 (14)
O10.0529 (10)0.0647 (10)0.0295 (8)−0.0162 (8)0.0016 (7)0.0032 (7)
O20.0597 (10)0.0663 (10)0.0278 (8)−0.0085 (9)0.0018 (7)−0.0025 (7)

Geometric parameters (Å, °)

C1—C101.368 (3)C8—H80.9300
C1—O11.375 (2)C9—C101.417 (3)
C1—C21.406 (3)C10—H100.9300
C2—C31.356 (3)C11—O11.424 (2)
C2—H20.9300C11—C121.454 (3)
C3—C41.414 (3)C11—H11A0.9700
C3—H30.9300C11—H11B0.9700
C4—C91.410 (3)C12—C131.160 (3)
C4—C51.415 (3)C13—H130.9300
C5—C61.357 (3)C14—O21.424 (3)
C5—H50.9300C14—C151.455 (3)
C6—C71.401 (3)C14—H14A0.9700
C6—H60.9300C14—H14B0.9700
C7—O21.364 (2)C15—C161.160 (3)
C7—C81.371 (3)C16—H160.9300
C8—C91.421 (3)
C10—C1—O1125.53 (18)C4—C9—C10119.59 (18)
C10—C1—C2120.75 (19)C4—C9—C8119.19 (17)
O1—C1—C2113.71 (17)C10—C9—C8121.22 (19)
C3—C2—C1120.12 (19)C1—C10—C9119.76 (19)
C3—C2—H2119.9C1—C10—H10120.1
C1—C2—H2119.9C9—C10—H10120.1
C2—C3—C4121.2 (2)O1—C11—C12107.91 (17)
C2—C3—H3119.4O1—C11—H11A110.1
C4—C3—H3119.4C12—C11—H11A110.1
C9—C4—C3118.59 (18)O1—C11—H11B110.1
C9—C4—C5118.69 (18)C12—C11—H11B110.1
C3—C4—C5122.72 (19)H11A—C11—H11B108.4
C6—C5—C4121.1 (2)C13—C12—C11177.9 (3)
C6—C5—H5119.4C12—C13—H13180.0
C4—C5—H5119.4O2—C14—C15108.50 (17)
C5—C6—C7120.38 (19)O2—C14—H14A110.0
C5—C6—H6119.8C15—C14—H14A110.0
C7—C6—H6119.8O2—C14—H14B110.0
O2—C7—C8125.5 (2)C15—C14—H14B110.0
O2—C7—C6114.03 (18)H14A—C14—H14B108.4
C8—C7—C6120.45 (19)C16—C15—C14176.9 (3)
C7—C8—C9120.13 (19)C15—C16—H16180.0
C7—C8—H8119.9C1—O1—C11117.76 (15)
C9—C8—H8119.9C7—O2—C14117.59 (15)
C10—C1—C2—C3−0.8 (3)C3—C4—C9—C8178.38 (18)
O1—C1—C2—C3179.76 (19)C5—C4—C9—C8−1.7 (3)
C1—C2—C3—C40.2 (3)C7—C8—C9—C41.5 (3)
C2—C3—C4—C91.2 (3)C7—C8—C9—C10−178.24 (18)
C2—C3—C4—C5−178.8 (2)O1—C1—C10—C9179.43 (17)
C9—C4—C5—C60.7 (3)C2—C1—C10—C90.1 (3)
C3—C4—C5—C6−179.4 (2)C4—C9—C10—C11.3 (3)
C4—C5—C6—C70.6 (3)C8—C9—C10—C1−179.01 (18)
C5—C6—C7—O2178.94 (19)C10—C1—O1—C11−1.4 (3)
C5—C6—C7—C8−0.8 (3)C2—C1—O1—C11178.01 (17)
O2—C7—C8—C9−179.92 (18)C12—C11—O1—C1−165.49 (18)
C6—C7—C8—C9−0.2 (3)C8—C7—O2—C143.4 (3)
C3—C4—C9—C10−1.9 (3)C6—C7—O2—C14−176.27 (18)
C5—C4—C9—C10178.05 (18)C15—C14—O2—C7−170.02 (17)

Hydrogen-bond geometry (Å, °)

Cg2 is the centroid of the C4–C9 benzene ring.
D—H···AD—HH···AD···AD—H···A
C13—H13···O2i0.932.543.465 (3)172
C14—H14B···O1ii0.972.573.533 (3)173
C11—H11A···Cg2ii0.972.673.526 (3)148

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

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: OM2339).

References

  • Bruker (1999). SMART and SAINT Bruker AXS Inc., Madison, Wisconsin, USA.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Srinivasan, R., Uttamchandani, M. & Yao, S. Q. (2006). Org. Lett.8, 713–716. [PubMed]

Articles from Acta Crystallographica Section E: Structure Reports Online are provided here courtesy of International Union of Crystallography