2,6-Bis(prop-2-yn­yloxy)naphthalene

Yao, L.; Tao, R.-J.

doi:10.1107/S1600536808031772

organic compounds

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ISSN: 2056-9890

Volume 64| Part 11| November 2008| Page o2081

doi:10.1107/S1600536808031772

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2,6-Bis(prop-2-ynyloxy)naphthalene

Li Yao ^a and Ruo-Jie Tao ^b ^*

^aSchool of Computer and Information Engineering, Henan University, Kaifeng 475001, Henan, People's Republic of China, and ^bInstitute of Molecular and Crystal Engineering, College of Chemistry and Chemical Engineering, Henan University, Kaifeng 475001, Henan, People's Republic of China
^*Correspondence e-mail: zhw@henu.edu.cn

(Received 28 September 2008; accepted 2 October 2008; online 9 October 2008)

The title compound, C₁₆H₁₂O₂, crystallizes with one half-molecule in the asymmetric unit. The molecule lies on an inversion centre, located at the mid-point of the naphthyl group. All non-H atoms are almost coplanar, with a mean deviation from the least-squares plane of 0.0536 (11) Å. 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 compound preparation, see: Burchell et al. (2006 ). For related structures, see: Zhang et al. (2008 ); Ghosh et al. (2007 ).

Experimental

Crystal data

C₁₆H₁₂O₂
M_r = 236.26
Orthorhombic, P b c a
a = 7.5783 (11) Å
b = 8.0295 (12) Å
c = 20.972 (3) Å
V = 1276.1 (3) Å³
Z = 4
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 293 (2) K
0.20 × 0.19 × 0.17 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005 ) T_min = 0.98, T_max = 0.99
6824 measured reflections
1250 independent reflections
952 reflections with I > 2σ(I)
R_int = 0.029

Refinement

R[F² > 2σ(F²)] = 0.039
wR(F²) = 0.099
S = 1.04
1250 reflections
82 parameters
H-atom parameters constrained
Δρ_max = 0.11 e Å⁻³
Δρ_min = −0.10 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 and Cg2 are the centroids of the C4–C7/C7ⁱ/C8 and C4ⁱ–C7ⁱ/C7/C8ⁱ rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C1—H1⋯O1ⁱ	0.93	2.56	3.385 (2)	148
C3—H3A⋯Cg1ⁱⁱ	0.97	2.76	3.579 (2)	143
C3—H3A⋯Cg2ⁱⁱⁱ	0.97	2.76	3.579 (2)	143
Symmetry codes: (i) $[-x+2, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (ii) $[-x+{\script{1\over 2}}, y-{\script{1\over 2}}, z]$ ; (iii) $[x-{\script{1\over 2}}, -y+{\script{3\over 2}}, -z]$ .

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/S1600536808031772/bg2213sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808031772/bg2213Isup2.hkl

checkCIF report

Comment top

The molecule of the title compound (Fig. 1) lies on an inversion center, placed at the midpoint of the naphthyl group. Except for H atoms of the methylenes, all the remaining atoms are almost coplanar, with a mean deviation from the least-square plane to be 0.0675 (11) Å. The bond lengths and angles are normal.

No classical hydrogen bonds or π—π interactions are observed. 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, Table 1). [Cg1 and Cg2 are the centroids of the C4—C7, C7ⁱ, C8 and C4ⁱ—C7ⁱ, C7, C8ⁱrings, respectively. Symmetry code: (i) -x + 2,-y + 1,-z.]

Related literature top

For compound preparation, see: Burchell et al. (2006). For related literature, see: Zhang et al. (2008); Ghosh et al. (2007).

Experimental top

The title compound was obtaind unintentionally as the product of an attempted synthesis of a network complex (Burchell et al., 2006) based on Co^II and 2,6-bis(prop-2-ynyloxy)naphthalene, by evaporation of a methyl alcohol and acetone solution of CoCl₂, NaN₃ and the title molecule, at 298 K. All chemical reagents were obtained commercially from Alfa Aesar Company and used without further purification.

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. 'A' labeled atoms are generated by symmetry code -x + 2,-y + 1,-z.
	Fig. 2. The three-dimensional supramolecular framework of the title complound formed by C—H···O and C—H···π(arene) hydrogen bonds.

2,6-Bis(prop-2-ynyloxy)naphthalene top

Crystal data top

C₁₆H₁₂O₂	F(000) = 496
M_r = 236.26	D_x = 1.230 Mg m⁻³
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 1948 reflections
a = 7.5783 (11) Å	θ = 2.7–26.2°
b = 8.0295 (12) Å	µ = 0.08 mm⁻¹
c = 20.972 (3) Å	T = 293 K
V = 1276.1 (3) Å³	Block, colourless
Z = 4	0.20 × 0.19 × 0.17 mm

Data collection top

Bruker SMART APEXII CCD area-detector diffractometer	1250 independent reflections
Radiation source: fine-focus sealed tube	952 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.029
ϕ and ω scans	θ_max = 26.0°, θ_min = 1.9°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −9→9
T_min = 0.98, T_max = 0.99	k = −9→9
6824 measured reflections	l = −12→25

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) = 0.099	H-atom parameters constrained
S = 1.04	w = 1/[σ²(F_o²) + (0.0447P)² + 0.1717P] where P = (F_o² + 2F_c²)/3
1250 reflections	(Δ/σ)_max < 0.001
82 parameters	Δρ_max = 0.11 e Å⁻³
0 restraints	Δρ_min = −0.10 e Å⁻³

Crystal data top

C₁₆H₁₂O₂	V = 1276.1 (3) Å³
M_r = 236.26	Z = 4
Orthorhombic, Pbca	Mo Kα radiation
a = 7.5783 (11) Å	µ = 0.08 mm⁻¹
b = 8.0295 (12) Å	T = 293 K
c = 20.972 (3) Å	0.20 × 0.19 × 0.17 mm

Data collection top

Bruker SMART APEXII CCD area-detector diffractometer	1250 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2005)	952 reflections with I > 2σ(I)
T_min = 0.98, T_max = 0.99	R_int = 0.029
6824 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.039	0 restraints
wR(F²) = 0.099	H-atom parameters constrained
S = 1.04	Δρ_max = 0.11 e Å⁻³
1250 reflections	Δρ_min = −0.10 e Å⁻³
82 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
O1	0.99206 (12)	0.82529 (11)	0.13702 (4)	0.0551 (3)
C1	0.9300 (3)	1.1886 (2)	0.21293 (9)	0.0939 (7)
H1	0.9416	1.2665	0.2455	0.113*
C2	0.9155 (2)	1.09120 (19)	0.17226 (8)	0.0662 (5)
C3	0.8995 (2)	0.97311 (17)	0.12002 (7)	0.0600 (4)
H3A	0.7762	0.9479	0.1123	0.072*
H3B	0.9492	1.0202	0.0814	0.072*
C4	1.00020 (16)	0.70096 (16)	0.09247 (7)	0.0473 (3)
C5	1.09064 (17)	0.55721 (17)	0.11300 (7)	0.0532 (4)
H5	1.1365	0.5528	0.1541	0.064*
C6	1.11120 (18)	0.42548 (16)	0.07337 (7)	0.0525 (4)
H6	1.1699	0.3313	0.0881	0.063*
C7	1.04565 (15)	0.42735 (15)	0.01009 (7)	0.0458 (3)
C8	0.93214 (16)	0.70846 (16)	0.03204 (6)	0.0481 (4)
H8	0.8713	0.8029	0.0187	0.058*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0576 (6)	0.0521 (6)	0.0555 (6)	0.0050 (5)	−0.0035 (5)	0.0030 (5)
C1	0.145 (2)	0.0720 (11)	0.0651 (12)	0.0012 (12)	0.0035 (12)	−0.0069 (10)
C2	0.0822 (11)	0.0563 (9)	0.0601 (10)	0.0052 (8)	0.0045 (8)	0.0045 (8)
C3	0.0666 (10)	0.0526 (8)	0.0609 (9)	0.0060 (7)	−0.0028 (7)	0.0032 (7)
C4	0.0400 (7)	0.0467 (7)	0.0553 (8)	−0.0026 (6)	0.0014 (6)	0.0045 (6)
C5	0.0497 (8)	0.0572 (8)	0.0525 (8)	0.0020 (7)	−0.0072 (6)	0.0088 (7)
C6	0.0476 (7)	0.0494 (7)	0.0603 (9)	0.0081 (6)	−0.0066 (6)	0.0109 (7)
C7	0.0364 (6)	0.0465 (7)	0.0546 (8)	−0.0008 (5)	−0.0014 (6)	0.0103 (6)
C8	0.0424 (7)	0.0446 (7)	0.0575 (9)	0.0042 (6)	−0.0021 (6)	0.0095 (6)

Geometric parameters (Å, º) top

O1—C4	1.3687 (16)	C5—C6	1.3541 (18)
O1—C3	1.4240 (16)	C5—H5	0.9300
C1—C2	1.162 (2)	C6—C7	1.417 (2)
C1—H1	0.9300	C6—H6	0.9300
C2—C3	1.454 (2)	C7—C8ⁱ	1.4136 (18)
C3—H3A	0.9700	C7—C7ⁱ	1.421 (2)
C3—H3B	0.9700	C8—C7ⁱ	1.4136 (18)
C4—C8	1.3695 (19)	C8—H8	0.9300
C4—C5	1.4098 (18)

C4—O1—C3	117.34 (10)	C6—C5—C4	120.54 (13)
C2—C1—H1	180.0	C6—C5—H5	119.7
C1—C2—C3	178.25 (18)	C4—C5—H5	119.7
O1—C3—C2	108.28 (12)	C5—C6—C7	121.74 (12)
O1—C3—H3A	110.0	C5—C6—H6	119.1
C2—C3—H3A	110.0	C7—C6—H6	119.1
O1—C3—H3B	110.0	C8ⁱ—C7—C6	122.38 (12)
C2—C3—H3B	110.0	C8ⁱ—C7—C7ⁱ	120.34 (15)
H3A—C3—H3B	108.4	C6—C7—C7ⁱ	117.28 (16)
O1—C4—C8	125.63 (12)	C4—C8—C7ⁱ	119.98 (12)
O1—C4—C5	114.25 (12)	C4—C8—H8	120.0
C8—C4—C5	120.11 (13)	C7ⁱ—C8—H8	120.0

C4—O1—C3—C2	−176.80 (12)	C4—C5—C6—C7	0.9 (2)
C3—O1—C4—C8	2.36 (19)	C5—C6—C7—C8ⁱ	179.27 (12)
C3—O1—C4—C5	−178.77 (11)	C5—C6—C7—C7ⁱ	−1.0 (2)
O1—C4—C5—C6	−178.91 (12)	O1—C4—C8—C7ⁱ	178.05 (12)
C8—C4—C5—C6	0.02 (19)	C5—C4—C8—C7ⁱ	−0.75 (19)

Symmetry code: (i) −x+2, −y+1, −z.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C1—H1···O1ⁱⁱ	0.93	2.56	3.385 (2)	148
C3—H3A···Cg1ⁱⁱⁱ	0.97	2.76	3.579 (2)	143
C3—H3A···Cg2^iv	0.97	2.76	3.579 (2)	143

Symmetry codes: (ii) −x+2, y+1/2, −z+1/2; (iii) −x+1/2, y−1/2, z; (iv) x−1/2, −y+3/2, −z.

Experimental details

Crystal data
Chemical formula	C₁₆H₁₂O₂
M_r	236.26
Crystal system, space group	Orthorhombic, Pbca
Temperature (K)	293
a, b, c (Å)	7.5783 (11), 8.0295 (12), 20.972 (3)
V (Å³)	1276.1 (3)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.08
Crystal size (mm)	0.20 × 0.19 × 0.17

Data collection
Diffractometer	Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2005)
T_min, T_max	0.98, 0.99
No. of measured, independent and observed [I > 2σ(I)] reflections	6824, 1250, 952
R_int	0.029
(sin θ/λ)_max (Å⁻¹)	0.617

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.039, 0.099, 1.04
No. of reflections	1250
No. of parameters	82
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.11, −0.10

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
C1—H1···O1ⁱ	0.93	2.56	3.385 (2)	148.1
C3—H3A···Cg1ⁱⁱ	0.97	2.759	3.579 (2)	142.66
C3—H3A···Cg2ⁱⁱⁱ	0.97	2.759	3.579 (2)	142.66

Symmetry codes: (i) −x+2, y+1/2, −z+1/2; (ii) −x+1/2, y−1/2, z; (iii) x−1/2, −y+3/2, −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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