supplementary materials
2,6-Bis(prop-2-ynyloxy)naphthalene
The title compound was obtaind unintentionally as the product of an attempted
synthesis of a network complex (Burchell et al., 2006) based on
CoII
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.
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. Uiso(H) = 1.2 Ueq (carrier C) for
all the H atoms.
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).
2,6-Bis(prop-2-ynyloxy)naphthalene
top
Crystal data top
| C16H12O2 | F(000) = 496 |
| Mr = 236.26 | Dx = 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 | Rint = 0.029 |
| φ and ω scans | θmax = 26.0°, θmin = 1.9° |
Absorption correction: multi-scan
(SADABS; Bruker, 2005) | h = −9→9 |
| Tmin = 0.98, Tmax = 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(Fo2) + (0.0447P)2 + 0.1717P]
where P = (Fo2 + 2Fc2)/3 |
| 1250 reflections | (Δ/σ)max < 0.001 |
| 82 parameters | Δρmax = 0.11 e Å−3 |
| 0 restraints | Δρmin = −0.10 e Å−3 |
Crystal data top
| C16H12O2 | V = 1276.1 (3) Å3 |
| Mr = 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) |
| Tmin = 0.98, Tmax = 0.99 | Rint = 0.029 |
| 6824 measured reflections | θmax = 26.0° |
Refinement top
| R[F2 > 2σ(F2)] = 0.039 | H-atom parameters constrained |
| wR(F2) = 0.099 | Δρmax = 0.11 e Å−3 |
| S = 1.04 | Δρmin = −0.10 e Å−3 |
| 1250 reflections | Absolute structure: ? |
| 82 parameters | Flack parameter: ? |
| 0 restraints | Rogers parameter: ? |
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 | Uiso*/Ueq | |
| 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, °) 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 codes: (i) −x+2, −y+1, −z. |
Hydrogen-bond geometry (Å, °) 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···Cg2iv | 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. |
Table 1
Hydrogen-bond geometry (Å, °) top
| 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+1/2, −z+1/2; (ii) −x+1/2, y−1/2, z; (iii) x−1/2, −y+3/2, −z. |
The authors are grateful for financial support from the Henan Administration of
Science and Technology (grant No. 0111030700).
Bruker (2005). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Burchell, T. J., Jennings, M. C. & Puddephatt, R. J. (2006). Inorg. Chim. Acta, 359, 2812–2818.
Ghosh, S., Mukhopadhyay, R., Helliwell, M. & Mukherjee, A. K. (2007). Acta Cryst. C63, o496–o500.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122.
Zhang, W., Yao, L. & Tao, R.-J. (2008). Acta Cryst. E64, o307.
O and C-H![[pi]](/logos/entities/pi_rmgif.gif)
(arene) hydrogen bonds.![[Figure 1]](./bg2213fig1thm.gif)
![[Figure 2]](./bg2213fig2thm.gif)
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, C8i rings, respectively. Symmetry code: (i) -x + 2,-y + 1,-z.]