2,3-Bis(prop-2-yn­yloxy)naphthalene

Yang, G.-Z.; Li, F.-A.

doi:10.1107/S1600536808037549

organic compounds

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ISSN: 2056-9890

Volume 64| Part 12| December 2008| Page o2383

doi:10.1107/S1600536808037549

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2,3-Bis(prop-2-ynyloxy)naphthalene

Guo-Zhong Yang ^a ^* and Fu-An Li ^b

^aCollege of Civil and Architectural Engineering, Henan University, Kaifeng 475001, Henan, People's Republic of China, and ^bCollege of Chemistry and Chemical Engineering, Pingdingshan University, Pingdingshan 467000, Henan, People's Republic of China
^*Correspondence e-mail: zhw@henu.edu.cn

(Received 30 September 2008; accepted 12 November 2008; online 20 November 2008)

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

Experimental

Crystal data

C₁₆H₁₂O₂
M_r = 236.26
Orthorhombic, P b c a
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 ) 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[F² > 2σ(F²)] = 0.039
wR(F²) = 0.101
S = 1.04
2182 reflections
163 parameters
H-atom parameters constrained
Δρ_max = 0.17 e Å⁻³
Δρ_min = −0.19 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C4–C6/C11–C13 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C16—H16⋯O2ⁱ	0.93	2.48	3.409 (2)	177
C3—H3A⋯Cg1ⁱⁱ	0.97	2.95	3.634 (2)	129
Symmetry codes: (i) $[-x, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (ii) $[-x-{\script{1\over 2}}, y-{\script{1\over 2}}, z]$ .

Data collection: APEX2 (Bruker, 2005); cell refinement: APEX2; data reduction: SAINT (Bruker, 2005); 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/S1600536808037549/bv2111sup1.cif

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

checkCIF report

Comment top

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≡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.]

Related literature top

For related structures, see: Zhang et al. (2008); Ghosh et al. (2007); Wang & Kong (2007). For the synthesis, see: Burchell et al. (2006). For bond-length data, see: Allen et al. (1987). For π–π stacking interactions, see: Steed & Atwood (2000). Cg1 id the centroid of the C4–C6/C11–C13 ring.

Experimental top

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.

Computing details top

Data collection: APEX2 (Bruker, 2005); cell refinement: APEX2 (Bruker, 2005); data reduction: SAINT (Bruker, 2005); 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. 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.

2,3-bis(prop-2-ynyloxy)naphthalene top

Crystal data top

C₁₆H₁₂O₂	F(000) = 992
M_r = 236.26	D_x = 1.265 Mg m⁻³
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 3821 reflections
a = 8.2921 (12) Å	θ = 2.8–25.7°
b = 9.0457 (14) Å	µ = 0.08 mm⁻¹
c = 33.070 (5) Å	T = 298 K
V = 2480.5 (6) Å³	Block, colourless
Z = 8	0.18 × 0.16 × 0.15 mm

Data collection top

Bruker SMART APEXII CCD area-detector diffractometer	2182 independent reflections
Radiation source: fine-focus sealed tube	1782 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.033
ω scans	θ_max = 25.0°, θ_min = 2.5°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −9→9
T_min = 0.984, T_max = 0.989	k = −10→10
12468 measured reflections	l = −39→29

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)] = 0.039	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.101	H-atom parameters constrained
S = 1.04	w = 1/[σ²(F_o²) + (0.0527P)² + 0.338P] where P = (F_o² + 2F_c²)/3
2182 reflections	(Δ/σ)_max < 0.001
163 parameters	Δρ_max = 0.17 e Å⁻³
0 restraints	Δρ_min = −0.19 e Å⁻³

Crystal data top

C₁₆H₁₂O₂	V = 2480.5 (6) Å³
M_r = 236.26	Z = 8
Orthorhombic, Pbca	Mo Kα radiation
a = 8.2921 (12) Å	µ = 0.08 mm⁻¹
b = 9.0457 (14) Å	T = 298 K
c = 33.070 (5) Å	0.18 × 0.16 × 0.15 mm

Data collection top

Bruker SMART APEXII CCD area-detector diffractometer	2182 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2005)	1782 reflections with I > 2σ(I)
T_min = 0.984, T_max = 0.989	R_int = 0.033
12468 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.039	0 restraints
wR(F²) = 0.101	H-atom parameters constrained
S = 1.04	Δρ_max = 0.17 e Å⁻³
2182 reflections	Δρ_min = −0.19 e Å⁻³
163 parameters

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

	x	y	z	U_iso*/U_eq
C1	−0.1360 (2)	−0.0848 (2)	0.32753 (6)	0.0752 (6)
H1	−0.1425	−0.1672	0.3108	0.090*
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	−0.2249	0.1865	0.3798	0.066*
H3B	−0.0720	0.1182	0.4009	0.066*
C4	0.00170 (15)	0.38601 (15)	0.37523 (4)	0.0400 (3)
C5	−0.05860 (17)	0.42250 (16)	0.41224 (4)	0.0462 (4)
H5	−0.1182	0.3532	0.4267	0.055*
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	−0.1609	0.5422	0.4811	0.070*
C8	−0.0727 (3)	0.7468 (2)	0.48143 (5)	0.0703 (5)
H8	−0.1182	0.7741	0.5060	0.084*
C9	0.0218 (2)	0.8480 (2)	0.45997 (5)	0.0696 (5)
H9	0.0401	0.9417	0.4706	0.084*
C10	0.0875 (2)	0.80997 (18)	0.42353 (5)	0.0577 (4)
H10	0.1500	0.8782	0.4095	0.069*
C11	0.06147 (17)	0.66812 (16)	0.40699 (4)	0.0443 (3)
C12	0.12274 (17)	0.62803 (15)	0.36856 (4)	0.0436 (3)
H12	0.1830	0.6959	0.3538	0.052*
C13	0.09452 (16)	0.49128 (15)	0.35298 (4)	0.0391 (3)
C14	0.24207 (18)	0.53826 (15)	0.29190 (4)	0.0447 (3)
H14A	0.3080	0.4809	0.2735	0.054*
H14B	0.3139	0.5947	0.3092	0.054*
C15	0.14206 (18)	0.64031 (16)	0.26860 (4)	0.0448 (4)
C16	0.0667 (2)	0.71916 (18)	0.24743 (5)	0.0575 (4)
H16	0.0073	0.7814	0.2307	0.069*
O1	−0.01832 (12)	0.25415 (10)	0.35571 (3)	0.0479 (3)
O2	0.14871 (12)	0.43928 (10)	0.31646 (3)	0.0471 (3)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0882 (14)	0.0598 (11)	0.0778 (12)	−0.0163 (10)	0.0254 (11)	−0.0032 (10)
C2	0.0584 (10)	0.0467 (9)	0.0672 (10)	−0.0065 (7)	0.0180 (8)	0.0088 (8)
C3	0.0586 (10)	0.0444 (8)	0.0631 (9)	−0.0032 (7)	0.0164 (8)	0.0104 (7)
C4	0.0354 (7)	0.0398 (7)	0.0448 (8)	0.0031 (6)	0.0005 (6)	0.0047 (6)
C5	0.0454 (8)	0.0499 (8)	0.0433 (8)	0.0030 (7)	0.0040 (6)	0.0117 (7)
C6	0.0448 (8)	0.0544 (9)	0.0361 (7)	0.0091 (7)	−0.0050 (6)	0.0042 (6)
C7	0.0660 (10)	0.0696 (11)	0.0403 (8)	0.0089 (8)	0.0054 (8)	0.0055 (8)
C8	0.0896 (14)	0.0803 (13)	0.0410 (8)	0.0154 (11)	0.0053 (9)	−0.0092 (8)
C9	0.0884 (13)	0.0660 (11)	0.0545 (10)	0.0014 (10)	−0.0006 (9)	−0.0156 (9)
C10	0.0643 (10)	0.0572 (9)	0.0517 (9)	−0.0036 (8)	−0.0007 (8)	−0.0081 (7)
C11	0.0418 (8)	0.0508 (8)	0.0403 (7)	0.0042 (6)	−0.0051 (6)	−0.0007 (6)
C12	0.0418 (8)	0.0453 (8)	0.0438 (8)	−0.0042 (6)	0.0031 (6)	0.0029 (6)
C13	0.0345 (7)	0.0440 (7)	0.0388 (7)	0.0025 (6)	0.0021 (6)	0.0022 (6)
C14	0.0452 (8)	0.0438 (7)	0.0453 (7)	−0.0025 (6)	0.0115 (7)	0.0018 (6)
C15	0.0497 (8)	0.0442 (8)	0.0405 (7)	−0.0073 (7)	0.0029 (7)	−0.0073 (6)
C16	0.0616 (10)	0.0558 (9)	0.0552 (9)	−0.0044 (8)	−0.0124 (8)	0.0009 (8)
O1	0.0499 (6)	0.0404 (5)	0.0535 (6)	−0.0050 (4)	0.0135 (5)	0.0027 (4)
O2	0.0535 (6)	0.0423 (5)	0.0454 (5)	−0.0060 (5)	0.0140 (5)	−0.0010 (4)

Geometric parameters (Å, º) top

C1—C2	1.168 (2)	C8—H8	0.9300
C1—H1	0.9300	C9—C10	1.367 (2)
C2—C3	1.452 (2)	C9—H9	0.9300
C3—O1	1.4299 (16)	C10—C11	1.412 (2)
C3—H3A	0.9700	C10—H10	0.9300
C3—H3B	0.9700	C11—C12	1.416 (2)
C4—C5	1.363 (2)	C12—C13	1.3603 (19)
C4—O1	1.3663 (16)	C12—H12	0.9300
C4—C13	1.4285 (18)	C13—O2	1.3718 (15)
C5—C6	1.418 (2)	C14—O2	1.4354 (16)
C5—H5	0.9300	C14—C15	1.461 (2)
C6—C7	1.414 (2)	C14—H14A	0.9700
C6—C11	1.416 (2)	C14—H14B	0.9700
C7—C8	1.360 (2)	C15—C16	1.179 (2)
C7—H7	0.9300	C16—H16	0.9300
C8—C9	1.399 (3)

C2—C1—H1	180.0	C10—C9—H9	119.8
C1—C2—C3	179.39 (17)	C8—C9—H9	119.8
O1—C3—C2	107.72 (12)	C9—C10—C11	120.64 (16)
O1—C3—H3A	110.2	C9—C10—H10	119.7
C2—C3—H3A	110.2	C11—C10—H10	119.7
O1—C3—H3B	110.2	C10—C11—C12	121.72 (14)
C2—C3—H3B	110.2	C10—C11—C6	119.03 (13)
H3A—C3—H3B	108.5	C12—C11—C6	119.23 (13)
C5—C4—O1	126.24 (12)	C13—C12—C11	120.74 (13)
C5—C4—C13	119.93 (13)	C13—C12—H12	119.6
O1—C4—C13	113.83 (11)	C11—C12—H12	119.6
C4—C5—C6	120.91 (13)	C12—C13—O2	126.08 (12)
C4—C5—H5	119.5	C12—C13—C4	120.25 (12)
C6—C5—H5	119.5	O2—C13—C4	113.67 (11)
C7—C6—C11	118.51 (14)	O2—C14—C15	112.73 (12)
C7—C6—C5	122.53 (14)	O2—C14—H14A	109.0
C11—C6—C5	118.93 (12)	C15—C14—H14A	109.0
C8—C7—C6	121.10 (16)	O2—C14—H14B	109.0
C8—C7—H7	119.4	C15—C14—H14B	109.0
C6—C7—H7	119.4	H14A—C14—H14B	107.8
C7—C8—C9	120.29 (16)	C16—C15—C14	175.37 (15)
C7—C8—H8	119.9	C15—C16—H16	180.0
C9—C8—H8	119.9	C4—O1—C3	117.03 (11)
C10—C9—C8	120.41 (17)	C13—O2—C14	117.45 (10)

O1—C4—C5—C6	−178.85 (12)	C10—C11—C12—C13	−179.18 (14)
C13—C4—C5—C6	0.5 (2)	C6—C11—C12—C13	−0.7 (2)
C4—C5—C6—C7	177.07 (13)	C11—C12—C13—O2	−179.26 (12)
C4—C5—C6—C11	−1.0 (2)	C11—C12—C13—C4	0.2 (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—C12	179.33 (12)
C6—C7—C8—C9	−0.5 (3)	C5—C4—C13—O2	179.43 (12)
C7—C8—C9—C10	0.9 (3)	O1—C4—C13—O2	−1.12 (16)
C8—C9—C10—C11	−0.2 (3)	C5—C4—O1—C3	3.1 (2)
C9—C10—C11—C12	177.43 (15)	C13—C4—O1—C3	−176.35 (12)
C9—C10—C11—C6	−1.0 (2)	C2—C3—O1—C4	177.75 (12)
C7—C6—C11—C10	1.4 (2)	C12—C13—O2—C14	−1.0 (2)
C5—C6—C11—C10	179.60 (13)	C4—C13—O2—C14	179.51 (11)
C7—C6—C11—C12	−177.05 (13)	C15—C14—O2—C13	−81.84 (15)
C5—C6—C11—C12	1.1 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C16—H16···O2ⁱ	0.93	2.48	3.409 (2)	177
C3—H3A···Cg1ⁱⁱ	0.97	2.95	3.634 (2)	129

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

Experimental details

Crystal data
Chemical formula	C₁₆H₁₂O₂
M_r	236.26
Crystal system, space group	Orthorhombic, Pbca
Temperature (K)	298
a, b, c (Å)	8.2921 (12), 9.0457 (14), 33.070 (5)
V (Å³)	2480.5 (6)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.08
Crystal size (mm)	0.18 × 0.16 × 0.15

Data collection
Diffractometer	Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2005)
T_min, T_max	0.984, 0.989
No. of measured, independent and observed [I > 2σ(I)] reflections	12468, 2182, 1782
R_int	0.033
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.039, 0.101, 1.04
No. of reflections	2182
No. of parameters	163
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.17, −0.19

Computer programs: APEX2 (Bruker, 2005), SAINT (Bruker, 2005), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C16—H16···O2ⁱ	0.93	2.48	3.409 (2)	177
C3—H3A···Cg1ⁱⁱ	0.97	2.95	3.634 (2)	129

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

Acknowledgements

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

References

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