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

Xue, W.; Lu, H.; Pang, T.

doi:10.1107/S1600536810020982

organic compounds

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Volume 66| Part 7| July 2010| Page o1610

doi:10.1107/S1600536810020982

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

Wei-jian Xue,^a ^* Hui Lu ^a and Tao Pang ^a

^aKey Laboratory of Pesticides and Chemical Biology of the Ministry of Education, College of Chemistry, Central China Normal University, Wuhan 430079, People's Republic of China
^*Correspondence e-mail: hehexueweijian@163.com

(Received 9 May 2010; accepted 2 June 2010; online 9 June 2010)

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 ).

Experimental

Crystal data

C₁₆H₁₂O₂
M_r = 236.26
Orthorhombic, P b c a
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[F² > 2σ(F²)] = 0.063
wR(F²) = 0.146
S = 1.02
2812 reflections
163 parameters
H-atom parameters constrained
Δρ_max = 0.17 e Å⁻³
Δρ_min = −0.23 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg2 is the centroid of the C4–C9 benzene ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C13—H13⋯O2ⁱ	0.93	2.54	3.465 (3)	172
C14—H14B⋯O1ⁱⁱ	0.97	2.57	3.533 (3)	173
C11—H11A⋯Cg2ⁱⁱ	0.97	2.67	3.526 (3)	148
Symmetry codes: (i) $[x, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ ; (ii) $[-x+2, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

Data collection: SMART (Bruker, 1999 ); cell refinement: SAINT (Bruker, 1999); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810020982/om2339sup1.cif

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

checkCIF report

Comment top

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).

Related literature top

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

Experimental top

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.

Computing details top

Data collection: SMART (Bruker, 1999); cell refinement: SAINT (Bruker, 1999); data reduction: SAINT (Bruker, 1999); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

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.

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

Crystal data top

C₁₆H₁₂O₂	F(000) = 992
M_r = 236.26	D_x = 1.262 Mg m⁻³
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 1273 reflections
a = 11.3742 (12) Å	θ = 3.0–22.2°
b = 8.1364 (9) Å	µ = 0.08 mm⁻¹
c = 26.880 (3) Å	T = 298 K
V = 2487.6 (5) Å³	Plate, colorless
Z = 8	0.16 × 0.12 × 0.04 mm

Data collection top

Bruker SMART 1000 diffractometer	1807 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.070
Graphite monochromator	θ_max = 27.5°, θ_min = 2.4°
ϕ and ω scans	h = −14→12
8492 measured reflections	k = −9→10
2812 independent reflections	l = −11→34

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.063	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.146	H-atom parameters constrained
S = 1.02	w = 1/[σ²(F_o²) + (0.0571P)²] where P = (F_o² + 2F_c²)/3
2812 reflections	(Δ/σ)_max = 0.001
163 parameters	Δρ_max = 0.17 e Å⁻³
0 restraints	Δρ_min = −0.23 e Å⁻³

Crystal data top

C₁₆H₁₂O₂	V = 2487.6 (5) Å³
M_r = 236.26	Z = 8
Orthorhombic, Pbca	Mo Kα radiation
a = 11.3742 (12) Å	µ = 0.08 mm⁻¹
b = 8.1364 (9) Å	T = 298 K
c = 26.880 (3) Å	0.16 × 0.12 × 0.04 mm

Data collection top

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

Refinement top

R[F² > 2σ(F²)] = 0.063	0 restraints
wR(F²) = 0.146	H-atom parameters constrained
S = 1.02	Δρ_max = 0.17 e Å⁻³
2812 reflections	Δρ_min = −0.23 e Å⁻³
163 parameters

Special details top

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) top

	x	y	z	U_iso*/U_eq
C1	0.88182 (18)	0.2124 (2)	0.28194 (7)	0.0385 (5)
C2	0.78099 (18)	0.1252 (3)	0.26709 (8)	0.0441 (5)
H2	0.7296	0.0839	0.2909	0.053*
C3	0.75854 (19)	0.1013 (3)	0.21809 (8)	0.0462 (6)
H3	0.6915	0.0437	0.2087	0.055*
C4	0.83522 (18)	0.1623 (2)	0.18105 (7)	0.0373 (5)
C5	0.8135 (2)	0.1425 (3)	0.12958 (8)	0.0479 (6)
H5	0.7458	0.0881	0.1192	0.057*
C6	0.8896 (2)	0.2014 (3)	0.09503 (8)	0.0486 (6)
H6	0.8733	0.1879	0.0614	0.058*
C7	0.99257 (19)	0.2824 (2)	0.10979 (7)	0.0410 (5)
C8	1.01698 (18)	0.3049 (2)	0.15926 (7)	0.0386 (5)
H8	1.0857	0.3584	0.1688	0.046*
C9	0.93755 (18)	0.2466 (2)	0.19607 (7)	0.0349 (5)
C10	0.95915 (17)	0.2723 (2)	0.24742 (7)	0.0356 (5)
H10	1.0256	0.3296	0.2576	0.043*
C11	0.9945 (2)	0.3094 (3)	0.35131 (8)	0.0511 (6)
H11A	0.9876	0.4270	0.3460	0.061*
H11B	1.0642	0.2707	0.3342	0.061*
C12	1.0032 (2)	0.2742 (3)	0.40422 (8)	0.0538 (6)
C13	1.0111 (2)	0.2413 (3)	0.44607 (10)	0.0777 (9)
H13	1.0173	0.2149	0.4796	0.093*
C14	1.1715 (2)	0.4069 (3)	0.08303 (7)	0.0486 (6)
H14A	1.2248	0.3255	0.0967	0.058*
H14B	1.1602	0.4926	0.1077	0.058*
C15	1.2208 (2)	0.4766 (3)	0.03774 (8)	0.0512 (6)
C16	1.2596 (2)	0.5391 (3)	0.00261 (10)	0.0727 (8)
H16	1.2907	0.5892	−0.0256	0.087*
O1	0.89297 (13)	0.22760 (17)	0.33268 (5)	0.0490 (4)
O2	1.06171 (14)	0.33243 (19)	0.07121 (5)	0.0513 (4)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0421 (13)	0.0378 (11)	0.0356 (11)	0.0007 (10)	−0.0013 (9)	0.0027 (9)
C2	0.0396 (13)	0.0481 (13)	0.0448 (13)	−0.0091 (10)	0.0048 (10)	0.0058 (10)
C3	0.0381 (13)	0.0467 (13)	0.0540 (14)	−0.0078 (10)	−0.0041 (10)	−0.0019 (11)
C4	0.0371 (13)	0.0350 (11)	0.0398 (11)	0.0014 (9)	−0.0048 (9)	−0.0021 (9)
C5	0.0450 (14)	0.0507 (13)	0.0479 (13)	−0.0044 (11)	−0.0123 (11)	−0.0066 (11)
C6	0.0592 (16)	0.0554 (14)	0.0312 (11)	0.0003 (12)	−0.0104 (10)	−0.0058 (10)
C7	0.0487 (14)	0.0408 (12)	0.0335 (11)	0.0012 (10)	−0.0006 (10)	−0.0022 (9)
C8	0.0406 (13)	0.0422 (12)	0.0329 (11)	−0.0031 (10)	−0.0035 (9)	−0.0013 (9)
C9	0.0390 (12)	0.0324 (10)	0.0331 (10)	0.0024 (9)	−0.0026 (9)	−0.0015 (8)
C10	0.0357 (12)	0.0377 (11)	0.0333 (10)	−0.0018 (9)	−0.0032 (8)	0.0012 (8)
C11	0.0502 (15)	0.0653 (15)	0.0377 (12)	−0.0113 (12)	0.0010 (10)	0.0041 (10)
C12	0.0550 (16)	0.0705 (16)	0.0358 (12)	−0.0158 (13)	0.0011 (11)	−0.0001 (11)
C13	0.078 (2)	0.119 (2)	0.0368 (14)	−0.0317 (17)	−0.0031 (13)	0.0089 (14)
C14	0.0537 (15)	0.0559 (14)	0.0361 (11)	−0.0011 (12)	0.0023 (10)	−0.0015 (10)
C15	0.0618 (16)	0.0499 (14)	0.0420 (13)	0.0013 (12)	0.0130 (11)	−0.0047 (11)
C16	0.092 (2)	0.0675 (17)	0.0582 (17)	−0.0010 (15)	0.0295 (15)	0.0021 (14)
O1	0.0529 (10)	0.0647 (10)	0.0295 (8)	−0.0162 (8)	0.0016 (7)	0.0032 (7)
O2	0.0597 (10)	0.0663 (10)	0.0278 (8)	−0.0085 (9)	0.0018 (7)	−0.0025 (7)

Geometric parameters (Å, º) top

C1—C10	1.368 (3)	C8—H8	0.9300
C1—O1	1.375 (2)	C9—C10	1.417 (3)
C1—C2	1.406 (3)	C10—H10	0.9300
C2—C3	1.356 (3)	C11—O1	1.424 (2)
C2—H2	0.9300	C11—C12	1.454 (3)
C3—C4	1.414 (3)	C11—H11A	0.9700
C3—H3	0.9300	C11—H11B	0.9700
C4—C9	1.410 (3)	C12—C13	1.160 (3)
C4—C5	1.415 (3)	C13—H13	0.9300
C5—C6	1.357 (3)	C14—O2	1.424 (3)
C5—H5	0.9300	C14—C15	1.455 (3)
C6—C7	1.401 (3)	C14—H14A	0.9700
C6—H6	0.9300	C14—H14B	0.9700
C7—O2	1.364 (2)	C15—C16	1.160 (3)
C7—C8	1.371 (3)	C16—H16	0.9300
C8—C9	1.421 (3)

C10—C1—O1	125.53 (18)	C4—C9—C10	119.59 (18)
C10—C1—C2	120.75 (19)	C4—C9—C8	119.19 (17)
O1—C1—C2	113.71 (17)	C10—C9—C8	121.22 (19)
C3—C2—C1	120.12 (19)	C1—C10—C9	119.76 (19)
C3—C2—H2	119.9	C1—C10—H10	120.1
C1—C2—H2	119.9	C9—C10—H10	120.1
C2—C3—C4	121.2 (2)	O1—C11—C12	107.91 (17)
C2—C3—H3	119.4	O1—C11—H11A	110.1
C4—C3—H3	119.4	C12—C11—H11A	110.1
C9—C4—C3	118.59 (18)	O1—C11—H11B	110.1
C9—C4—C5	118.69 (18)	C12—C11—H11B	110.1
C3—C4—C5	122.72 (19)	H11A—C11—H11B	108.4
C6—C5—C4	121.1 (2)	C13—C12—C11	177.9 (3)
C6—C5—H5	119.4	C12—C13—H13	180.0
C4—C5—H5	119.4	O2—C14—C15	108.50 (17)
C5—C6—C7	120.38 (19)	O2—C14—H14A	110.0
C5—C6—H6	119.8	C15—C14—H14A	110.0
C7—C6—H6	119.8	O2—C14—H14B	110.0
O2—C7—C8	125.5 (2)	C15—C14—H14B	110.0
O2—C7—C6	114.03 (18)	H14A—C14—H14B	108.4
C8—C7—C6	120.45 (19)	C16—C15—C14	176.9 (3)
C7—C8—C9	120.13 (19)	C15—C16—H16	180.0
C7—C8—H8	119.9	C1—O1—C11	117.76 (15)
C9—C8—H8	119.9	C7—O2—C14	117.59 (15)

C10—C1—C2—C3	−0.8 (3)	C3—C4—C9—C8	178.38 (18)
O1—C1—C2—C3	179.76 (19)	C5—C4—C9—C8	−1.7 (3)
C1—C2—C3—C4	0.2 (3)	C7—C8—C9—C4	1.5 (3)
C2—C3—C4—C9	1.2 (3)	C7—C8—C9—C10	−178.24 (18)
C2—C3—C4—C5	−178.8 (2)	O1—C1—C10—C9	179.43 (17)
C9—C4—C5—C6	0.7 (3)	C2—C1—C10—C9	0.1 (3)
C3—C4—C5—C6	−179.4 (2)	C4—C9—C10—C1	1.3 (3)
C4—C5—C6—C7	0.6 (3)	C8—C9—C10—C1	−179.01 (18)
C5—C6—C7—O2	178.94 (19)	C10—C1—O1—C11	−1.4 (3)
C5—C6—C7—C8	−0.8 (3)	C2—C1—O1—C11	178.01 (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—C14	3.4 (3)
C3—C4—C9—C10	−1.9 (3)	C6—C7—O2—C14	−176.27 (18)
C5—C4—C9—C10	178.05 (18)	C15—C14—O2—C7	−170.02 (17)

Hydrogen-bond geometry (Å, º) top

Cg2 is the centroid of the C4–C9 benzene ring.

D—H···A	D—H	H···A	D···A	D—H···A
C13—H13···O2ⁱ	0.93	2.54	3.465 (3)	172
C14—H14B···O1ⁱⁱ	0.97	2.57	3.533 (3)	173
C11—H11A···Cg2ⁱⁱ	0.97	2.67	3.526 (3)	148

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

Experimental details

Crystal data
Chemical formula	C₁₆H₁₂O₂
M_r	236.26
Crystal system, space group	Orthorhombic, Pbca
Temperature (K)	298
a, b, c (Å)	11.3742 (12), 8.1364 (9), 26.880 (3)
V (Å³)	2487.6 (5)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.08
Crystal size (mm)	0.16 × 0.12 × 0.04

Data collection
Diffractometer	Bruker SMART 1000 diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	8492, 2812, 1807
R_int	0.070
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.063, 0.146, 1.02
No. of reflections	2812
No. of parameters	163
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.17, −0.23

Computer programs: SMART (Bruker, 1999), SAINT (Bruker, 1999), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

Cg2 is the centroid of the C4–C9 benzene ring.

D—H···A	D—H	H···A	D···A	D—H···A
C13—H13···O2ⁱ	0.93	2.54	3.465 (3)	172
C14—H14B···O1ⁱⁱ	0.97	2.57	3.533 (3)	173
C11—H11A···Cg2ⁱⁱ	0.97	2.67	3.526 (3)	148

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

Acknowledgements

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

References

Bruker (1999). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Srinivasan, R., Uttamchandani, M. & Yao, S. Q. (2006). Org. Lett. 8, 713–716. Web of Science CrossRef PubMed CAS Google Scholar

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CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 66| Part 7| July 2010| Page o1610

doi:10.1107/S1600536810020982

Open

access