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access(Naphthalene-1,4-diyl)dimethyl dibenzoate
aDepartment of Chemistry, ZunYi Normal College, ZunYi 563002, People's Republic of China
*Correspondence e-mail: liangyou_xia@126.com
In the title compound, C26H20O4, the complete molecule is generated by a crystallographic 2-fold axis and the naphthalene ring system is planar within 0.05 (4) Å. The dihedral angles between the –COO plane, the benzene ring and naphthalene ring system are 12.83 (3) and 12.93 (1)°, respectively. The –COO plane and the benzene ring are almost coplanar, forming a dihedral angle of 2.59 (8)°.
Related literature
For applications of related naphthalene derivatives, see: Fukuzumi et al. (1994![[Fukuzumi, T., Tajiri, T., Tsukada, H. & Yoshida, J. (1994). Jpn Patent JP 06 298919.]](../../../../../../logos/arrows/e_arr.gif "Fukuzumi, T., Tajiri, T., Tsukada, H. & Yoshida, J. (1994). Jpn Patent JP 06 298919.")
); Madsen et al. (2002); Strey & Voss (1998); Tsukada et al. (1994).
![[Scheme 1]](om2316scheme1.gif)
Experimental
Crystal data
|
Data collection: APEX2 (Bruker, 2004); cell SAINT (Bruker, 2004); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: XP in SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXL97.
Supporting information
contains datablocks global, I. DOI: 10.1107/S1600536810008391/om2316sup1.cif
Structure factors: contains datablock I. DOI: 10.1107/S1600536810008391/om2316Isup2.hkl
The title compound was synthesized according to the reported procedure of Strey & Voss (1998) and Madsen et al. (2002). Colourless single crystals suitable for X-ray diffraction were obtained by recrystallization from ethyl acetate.
H atoms were positioned geometrically, with C-H = 0.93 and 0.97Å for aromatic and methylene H atoms, respectively, and constrained to ride on their parent atoms, Uiso(H)= 1.2Ueq(C). In the absence of significant Friedel opposites were merged (862 Friedel pairs).
Data collection: APEX2 (Bruker, 2004); cell SAINT (Bruker, 2004); data reduction: SAINT (Bruker, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: XP in SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).
![[Figure 1]](./om2316fig1thm.gif) | Fig. 1. The molecular structure of the title compound showing 30% probability displacement ellipsoids and the atomic numbering. Symmetry code: A = 1.5 -x,0.5-y, z. |
| C26H20O4 | F(000) = 1664 |
| Mr = 396.42 | Dx = 1.346 Mg m−3 |
| Orthorhombic, Fdd2 | Mo Kα radiation, λ = 0.71073 Å |
| Hall symbol: F 2 -2 d | Cell parameters from 1789 reflections |
| a = 3.9919 (6) Å | θ = 2.6–25.3° |
| b = 60.385 (8) Å | µ = 0.09 mm−1 |
| c = 16.231 (2) Å | T = 296 K |
| V = 3912.5 (9) Å3 | Block, colourless |
| Z = 8 | 0.50 × 0.38 × 0.07 mm |
| Bruker APEXII diffractometer | 937 independent reflections |
| Radiation source: fine-focus sealed tube | 822 reflections with I > 2σ(I) |
| Graphite monochromator | Rint = 0.027 |
| ϕ and ω scans | θmax = 25.5°, θmin = 2.6° |
| Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −4→4 |
| Tmin = 0.957, Tmax = 0.994 | k = −72→72 |
| 6343 measured reflections | l = −19→19 |
| 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)] = 0.033 | Hydrogen site location: inferred from neighbouring sites |
| wR(F2) = 0.081 | H-atom parameters constrained |
| S = 1.08 | w = 1/[σ2(Fo2) + (0.0506P)2] where P = (Fo2 + 2Fc2)/3 |
| 937 reflections | (Δ/σ)max < 0.001 |
| 136 parameters | Δρmax = 0.10 e Å−3 |
| 1 restraint | Δρmin = −0.15 e Å−3 |
| C26H20O4 | V = 3912.5 (9) Å3 |
| Mr = 396.42 | Z = 8 |
| Orthorhombic, Fdd2 | Mo Kα radiation |
| a = 3.9919 (6) Å | µ = 0.09 mm−1 |
| b = 60.385 (8) Å | T = 296 K |
| c = 16.231 (2) Å | 0.50 × 0.38 × 0.07 mm |
| Bruker APEXII diffractometer | 937 independent reflections |
| Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | 822 reflections with I > 2σ(I) |
| Tmin = 0.957, Tmax = 0.994 | Rint = 0.027 |
| 6343 measured reflections |
| R[F2 > 2σ(F2)] = 0.033 | 1 restraint |
| wR(F2) = 0.081 | H-atom parameters constrained |
| S = 1.08 | Δρmax = 0.10 e Å−3 |
| 937 reflections | Δρmin = −0.15 e Å−3 |
| 136 parameters |
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 > 2sigma(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. |
| x | y | z | Uiso*/Ueq | ||
| O1 | 0.1416 (5) | 0.16848 (3) | 0.65497 (12) | 0.0680 (6) | |
| O2 | 0.4250 (4) | 0.19760 (2) | 0.60506 (10) | 0.0507 (4) | |
| C1 | 0.2722 (6) | 0.17767 (3) | 0.59764 (15) | 0.0467 (5) | |
| C2 | 0.2903 (6) | 0.16879 (3) | 0.51236 (15) | 0.0452 (5) | |
| C3 | 0.1552 (6) | 0.14804 (3) | 0.49816 (16) | 0.0556 (7) | |
| H3 | 0.0516 | 0.1404 | 0.5408 | 0.067* | |
| C4 | 0.1746 (8) | 0.13876 (4) | 0.42042 (17) | 0.0652 (8) | |
| H4 | 0.0881 | 0.1247 | 0.4112 | 0.078* | |
| C5 | 0.3209 (7) | 0.15021 (4) | 0.35675 (18) | 0.0655 (7) | |
| H5 | 0.3302 | 0.1440 | 0.3044 | 0.079* | |
| C6 | 0.4533 (7) | 0.17084 (4) | 0.37037 (17) | 0.0611 (7) | |
| H6 | 0.5522 | 0.1786 | 0.3272 | 0.073* | |
| C7 | 0.4407 (7) | 0.18018 (4) | 0.44775 (16) | 0.0522 (6) | |
| H7 | 0.5328 | 0.1941 | 0.4568 | 0.063* | |
| C8 | 0.4461 (6) | 0.20608 (3) | 0.68748 (14) | 0.0455 (5) | |
| H8A | 0.5784 | 0.1961 | 0.7213 | 0.055* | |
| H8B | 0.2236 | 0.2071 | 0.7112 | 0.055* | |
| C9 | 0.6053 (5) | 0.22851 (3) | 0.68603 (13) | 0.0413 (5) | |
| C10 | 0.6767 (5) | 0.23923 (3) | 0.76281 (14) | 0.0391 (5) | |
| C11 | 0.6072 (6) | 0.22913 (4) | 0.83964 (14) | 0.0474 (6) | |
| H11 | 0.5109 | 0.2151 | 0.8405 | 0.057* | |
| C12 | 0.6774 (7) | 0.23935 (4) | 0.91223 (14) | 0.0537 (6) | |
| H12 | 0.6296 | 0.2323 | 0.9618 | 0.064* | |
| C13 | 0.6778 (6) | 0.23930 (4) | 0.61428 (14) | 0.0468 (6) | |
| H13 | 0.6314 | 0.2324 | 0.5643 | 0.056* |
| U11 | U22 | U33 | U12 | U13 | U23 | |
| O1 | 0.0943 (15) | 0.0554 (11) | 0.0542 (11) | −0.0234 (10) | 0.0100 (11) | 0.0017 (9) |
| O2 | 0.0665 (11) | 0.0417 (8) | 0.0440 (9) | −0.0096 (7) | 0.0002 (8) | −0.0032 (7) |
| C1 | 0.0565 (14) | 0.0351 (10) | 0.0486 (13) | −0.0024 (10) | −0.0037 (11) | 0.0034 (11) |
| C2 | 0.0506 (13) | 0.0390 (11) | 0.0458 (13) | 0.0011 (9) | −0.0074 (10) | 0.0022 (10) |
| C3 | 0.0679 (17) | 0.0407 (12) | 0.0582 (17) | −0.0059 (11) | −0.0134 (13) | 0.0024 (11) |
| C4 | 0.087 (2) | 0.0445 (13) | 0.0640 (18) | −0.0039 (13) | −0.0223 (15) | −0.0045 (13) |
| C5 | 0.084 (2) | 0.0592 (15) | 0.0538 (15) | 0.0109 (14) | −0.0130 (14) | −0.0110 (14) |
| C6 | 0.0730 (18) | 0.0615 (16) | 0.0488 (15) | 0.0047 (13) | 0.0000 (13) | 0.0010 (12) |
| C7 | 0.0627 (15) | 0.0423 (11) | 0.0517 (14) | −0.0017 (11) | −0.0027 (12) | 0.0001 (11) |
| C8 | 0.0526 (13) | 0.0420 (11) | 0.0418 (13) | −0.0017 (10) | −0.0006 (11) | −0.0024 (11) |
| C9 | 0.0441 (13) | 0.0398 (11) | 0.0399 (13) | 0.0027 (9) | −0.0010 (10) | 0.0006 (10) |
| C10 | 0.0412 (11) | 0.0398 (10) | 0.0362 (11) | 0.0054 (9) | 0.0006 (10) | 0.0003 (10) |
| C11 | 0.0558 (15) | 0.0422 (11) | 0.0442 (13) | −0.0007 (10) | 0.0014 (12) | 0.0053 (11) |
| C12 | 0.0667 (17) | 0.0573 (14) | 0.0371 (13) | 0.0034 (11) | 0.0039 (12) | 0.0064 (10) |
| C13 | 0.0598 (14) | 0.0445 (11) | 0.0362 (12) | −0.0047 (10) | −0.0032 (11) | −0.0040 (10) |
| O1—C1 | 1.202 (3) | C7—H7 | 0.9300 |
| O2—C1 | 1.354 (3) | C8—C9 | 1.496 (3) |
| O2—C8 | 1.435 (3) | C8—H8A | 0.9700 |
| C1—C2 | 1.486 (3) | C8—H8B | 0.9700 |
| C2—C3 | 1.384 (3) | C9—C13 | 1.365 (3) |
| C2—C7 | 1.390 (3) | C9—C10 | 1.433 (3) |
| C3—C4 | 1.383 (4) | C10—C11 | 1.416 (3) |
| C3—H3 | 0.9300 | C10—C10i | 1.426 (4) |
| C4—C5 | 1.374 (4) | C11—C12 | 1.359 (3) |
| C4—H4 | 0.9300 | C11—H11 | 0.9300 |
| C5—C6 | 1.371 (4) | C12—C12i | 1.410 (5) |
| C5—H5 | 0.9300 | C12—H12 | 0.9300 |
| C6—C7 | 1.378 (4) | C13—C13i | 1.415 (4) |
| C6—H6 | 0.9300 | C13—H13 | 0.9300 |
| C1—O2—C8 | 115.25 (18) | O2—C8—C9 | 109.48 (18) |
| O1—C1—O2 | 122.4 (2) | O2—C8—H8A | 109.8 |
| O1—C1—C2 | 125.1 (2) | C9—C8—H8A | 109.8 |
| O2—C1—C2 | 112.43 (19) | O2—C8—H8B | 109.8 |
| C3—C2—C7 | 119.4 (2) | C9—C8—H8B | 109.8 |
| C3—C2—C1 | 117.6 (2) | H8A—C8—H8B | 108.2 |
| C7—C2—C1 | 123.03 (19) | C13—C9—C10 | 118.96 (18) |
| C4—C3—C2 | 119.8 (2) | C13—C9—C8 | 122.36 (19) |
| C4—C3—H3 | 120.1 | C10—C9—C8 | 118.67 (18) |
| C2—C3—H3 | 120.1 | C11—C10—C10i | 118.26 (12) |
| C5—C4—C3 | 120.4 (2) | C11—C10—C9 | 122.17 (17) |
| C5—C4—H4 | 119.8 | C10i—C10—C9 | 119.57 (11) |
| C3—C4—H4 | 119.8 | C12—C11—C10 | 121.8 (2) |
| C6—C5—C4 | 120.0 (3) | C12—C11—H11 | 119.1 |
| C6—C5—H5 | 120.0 | C10—C11—H11 | 119.1 |
| C4—C5—H5 | 120.0 | C11—C12—C12i | 119.92 (13) |
| C5—C6—C7 | 120.3 (3) | C11—C12—H12 | 120.0 |
| C5—C6—H6 | 119.8 | C12i—C12—H12 | 120.0 |
| C7—C6—H6 | 119.8 | C9—C13—C13i | 121.47 (12) |
| C6—C7—C2 | 120.1 (2) | C9—C13—H13 | 119.3 |
| C6—C7—H7 | 120.0 | C13i—C13—H13 | 119.3 |
| C2—C7—H7 | 120.0 | ||
| C8—O2—C1—O1 | 5.3 (3) | C1—C2—C7—C6 | 179.0 (2) |
| C8—O2—C1—C2 | −174.01 (19) | C1—O2—C8—C9 | −177.40 (18) |
| O1—C1—C2—C3 | −2.0 (4) | O2—C8—C9—C13 | 6.7 (3) |
| O2—C1—C2—C3 | 177.2 (2) | O2—C8—C9—C10 | −174.77 (18) |
| O1—C1—C2—C7 | 179.2 (3) | C13—C9—C10—C11 | 179.7 (2) |
| O2—C1—C2—C7 | −1.6 (3) | C8—C9—C10—C11 | 1.2 (3) |
| C7—C2—C3—C4 | 0.8 (4) | C13—C9—C10—C10i | −0.4 (3) |
| C1—C2—C3—C4 | −178.1 (2) | C8—C9—C10—C10i | −179.0 (2) |
| C2—C3—C4—C5 | −1.4 (4) | C10i—C10—C11—C12 | −0.2 (4) |
| C3—C4—C5—C6 | 1.0 (4) | C9—C10—C11—C12 | 179.7 (2) |
| C4—C5—C6—C7 | 0.0 (4) | C10—C11—C12—C12i | 0.2 (5) |
| C5—C6—C7—C2 | −0.6 (4) | C10—C9—C13—C13i | 0.2 (4) |
| C3—C2—C7—C6 | 0.2 (4) | C8—C9—C13—C13i | 178.7 (3) |
| Symmetry code: (i) −x+3/2, −y+1/2, z. |
Experimental details
| Crystal data | |
| Chemical formula | C26H20O4 |
| Mr | 396.42 |
| Crystal system, space group | Orthorhombic, Fdd2 |
| Temperature (K) | 296 |
| a, b, c (Å) | 3.9919 (6), 60.385 (8), 16.231 (2) |
| V (Å3) | 3912.5 (9) |
| Z | 8 |
| Radiation type | Mo Kα |
| µ (mm−1) | 0.09 |
| Crystal size (mm) | 0.50 × 0.38 × 0.07 |
| Data collection | |
| Diffractometer | Bruker APEXII diffractometer |
| Absorption correction | Multi-scan (SADABS; Sheldrick, 1996) |
| Tmin, Tmax | 0.957, 0.994 |
| No. of measured, independent and observed [I > 2σ(I)] reflections | 6343, 937, 822 |
| Rint | 0.027 |
| (sin θ/λ)max (Å−1) | 0.606 |
| Refinement | |
| R[F2 > 2σ(F2)], wR(F2), S | 0.033, 0.081, 1.08 |
| No. of reflections | 937 |
| No. of parameters | 136 |
| No. of restraints | 1 |
| H-atom treatment | H-atom parameters constrained |
| Δρmax, Δρmin (e Å−3) | 0.10, −0.15 |
Computer programs: APEX2 (Bruker, 2004), SAINT (Bruker, 2004), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), XP in SHELXTL (Sheldrick, 2008).
Acknowledgements
This work was supported by the Science and Technology Foundation of Zunyi City of China (No. 200723)
References
Bruker (2004). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Fukuzumi, T., Tajiri, T., Tsukada, H. & Yoshida, J. (1994). Jpn Patent JP 06 298919. Google Scholar
Madsen, P. et al. (2002). J. Med. Chem. 45, 5755–5775. Web of Science CrossRef PubMed CAS Google Scholar
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Strey, K. & Voss, J. (1998). J. Chem. Res. (S.), pp. 110–111; J. Chem. Res. (M.), pp. 648–682. Google Scholar
Tsukada, H., Tajiri, T., Fukuzumi, T. & Yoshida, J. (1994). Jpn Patent JP 06 298918. Google Scholar
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| CRYSTALLOGRAPHIC COMMUNICATIONS |
Numerous 1,4-naphthalene derivatives have been synthesized and studied. 1,4-naphthalene derivatives are important intermediates for applications such as monomers in the preparation of polymers (Fukuzumi et al., 1994; Tsukada et al., 1994). The title compound has a 2-fold axis of symmetry passing through the long axis of napthalene (Fig. 1). The naphthalene ring system is planar within 0.05 (4)A°. The dihedral angles of the C1/O1/O2 plane, the C2—C7 ring and naphthalene ring are 12.83 (3)° and 12.93 (1)°, respectively. Molecules of the title compound are closely stacked with a repeat equal to the a-axial dimension.