2,3-Bis(prop-2-yn­yloxy)naphthalene

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.

Key indicators

• Single-crystal X-ray study
• T = 298 K
• Mean [sigma](C-C)= 0.002 Å
• R factor = 0.039
• wR factor = 0.101
• Data-to-parameter ratio = 13.4

checkCIF/PLATON results

No syntax errors found


No errors found in this datablock

---

S1. 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≡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

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.

S2. 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.

S3. 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. U_iso(H) = 1.2 U_eq (carrier C) for all the H atoms.

Computing details

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

	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

Crystal data

C16H12O2	F(000) = 992
Mr = 236.26	Dx = 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) Å^3	Block, colourless
Z = 8	0.18 × 0.16 × 0.15 mm

Data collection

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

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.039	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.101	H-atom parameters constrained
S = 1.04	w = 1/[σ^2(Fo^2) + (0.0527P)^2 + 0.338P] where P = (Fo^2 + 2Fc^2)/3
2182 reflections	(Δ/σ)max < 0.001
163 parameters	Δρmax = 0.17 e Å^−3
0 restraints	Δρmin = −0.19 e Å^−3

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 (Ų)

	x	y	z	Uiso*/Ueq
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 (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
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)

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)

D—H···A	D—H	H···A	D···A	D—H···A
C16—H16···O2^i	0.93	2.48	3.409 (2)	177
C3—H3A···Cg1^ii	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.