organic compounds
Trimethyl 3,3′,3′′-(benzene-1,3,5-triyl)tripropynoate
aInstitut für Organische Chemie, TU Bergakademie Freiberg, Leipziger Strasse 29, D-09596 Freiberg/Sachsen, Germany, and bSchool of Pharmacy, University of Lincoln, Joseph Banks Laboratories, Green Lane, Lincoln LN6 7DL, England
*Correspondence e-mail: edwin.weber@chemie.tu-freiberg.de
In the title compound, C18H12O6, the alkyne bonds are distorted, featuring bond angles around the C—C≡C—C group of 173.6 (1)/179.0 (1), 178.1 (1)/178.4 (1) and 174.9 (1)/175.9 (1)°, and the ester groups make angles of 3.5 (1), 13.8 (1) and 14.5 (1)° with the central benzene ring. In the crystal, molecules are connected in layers parallel to (131) by weak C—H⋯O hydrogen bonds, giving rise to a system of hydrogen-bonded ring motifs with graph sets R22(14) and R44(22). The layers are linked by C—H⋯O and C—H⋯π contacts.
CCDC reference: 1474004
Structure description
The title compound, C18H12O6, is an interesting synthetic intermediate for the preparation of application–oriented solid materials involving both porous coordination polymers (MacGillivray, 2010) or metal-organic frameworks (Noro & Kitagawa, 2010) and crystalline inclusion hosts (Weber, 1996; Katzsch et al., 2016).
In the structure of the molecule (Fig. 1), the alkyne bonds are distorted which is shown by the corresponding bond angles [C2—C3—C4 = 173.6 (1), C3—C4—C13 = 179.0 (1), C6—C7—C8 = 178.1 (1), C7—C8—C15 = 178.4 (1), C10—C11—C12 = 174.9 (1), C11—C12—C17 = 175.9 (1)°] and the ester functions are not arranged in the benzene plane [interplanar angles: 3.5 (1) (C2, O1, O2), 13.8 (1) (C6, O3, O4) and 14.5 (1)° (C10, O5, O10)].
In the crystal, molecules are connected in layers parallel to (131) by weak C-H⋯O hydrogen bonds (Desiraju & Steiner, 1999) (Table 1) giving rise to hydrogen-bonded ring motifs with graph sets R22(14) and R44(22) (Fig. 2). The layers are linked by weak C—H⋯O contacts and additionally by C—H⋯π interactions.
Synthesis and crystallization
The title compound was prepared from 1,3,5-triethynylbenzene (Münch et al., 2013) and methyl chloroformiate as described in the literature (Katzsch et al., 2016). Colorless single crystals of prismatic shape suitable for X-ray diffraction were obtained by slow crystallization from a solvent mixture of acetone, ethyl acetate and n-hexane. For the synthesis of a related compound, see: Welti & Diederich (2003).
Refinement
Crystal data, data collection and structure .
details are summarized in Table 2
|
Structural data
CCDC reference: 1474004
10.1107/S2414314616006295/zp4005sup1.cif
contains datablock I. DOI:Structure factors: contains datablock I. DOI: 10.1107/S2414314616006295/zp4005Isup2.hkl
Supporting information file. DOI: 10.1107/S2414314616006295/zp4005Isup3.cml
The title compound was prepared from 1,3,5-triethynylbenzene (Münch et al., 2013) and methyl chloroformiate as described in the literature (Katzsch et al., 2016). Colorless single crystals of prismatic shape suitable for X-ray diffraction were obtained by slow crystallization from a solvent mixture of acetone, ethyl acetate and n-hexane. For the synthesis of a related compound, see: Welti & Diederich (2003).
The title compound, C18H12O6, is an interesting synthetic intermediate for the preparation of application–oriented solid materials involving both porous coordination polymers (MacGillivray, 2010) or metal-organic frameworks (Noro & Kitagawa, 2010) and crystalline inclusion hosts (Weber, 1996; Katzsch et al., 2016).
In the structure of the molecule (Fig. 1), the alkyne bonds are distorted which is shown by the corresponding bond angles [C2—C3—C4 = 173.6 (1), C3—C4—C13 = 179.0 (1), C6—C7—C8 = 178.1 (1), C7—C8—C15 = 178.4 (1), C10—C11—C12 = 174.9 (1), C11—C12—C17 = 175.9 (1)°] and the ester functions are not arranged in the benzene plane [interplanar angles: 3.5 (1) (C2, O1, O2), 13.8 (1) (C6, O3, O4) and 14.5° (C10, O5, O10)].
In the crystal, molecules are connected in layers parallel to (131) by weak C-H···O hydrogen bonds (Desiraju & Steiner, 1999) (Table 1) giving rise to hydrogen-bonded ring motifs with the graph sets R22(14) and R44(22) (Fig. 2). The layers are linked by weak C—H···O contacts and additionally by C—H···π interactions.
Data collection: APEX2 (Bruker, 2008); cell
SAINT (Bruker, 2008); data reduction: SAINT (Bruker, 2008); 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).Fig. 1. A view of the molecular structure of the title compound, with atom labelling. Displacement ellipsoids are drawn at the 50% probability level. | |
Fig. 2. A partial view of the crystal packing of the title compound, showing the formation of the C—H···O bonded layer structure, enclosing the system of R22(14) and R44(22) ring motifs. Hydrogen bonds are indicated by dashed lines. |
C18H12O6 | Z = 2 |
Mr = 324.28 | F(000) = 336 |
Triclinic, P1 | Dx = 1.369 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 8.5765 (2) Å | Cell parameters from 9912 reflections |
b = 9.8469 (2) Å | θ = 2.8–35.9° |
c = 10.2677 (2) Å | µ = 0.10 mm−1 |
α = 78.903 (1)° | T = 100 K |
β = 79.552 (1)° | Prism, colourless |
γ = 68.655 (1)° | 0.54 × 0.43 × 0.37 mm |
V = 786.65 (3) Å3 |
Bruker APEXII CCD diffractometer | 2769 independent reflections |
Radiation source: fine-focus sealed tube | 2558 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.022 |
φ and ω scans | θmax = 25.0°, θmin = 2.0° |
Absorption correction: multi-scan (SADABS; Sheldrick, 2004) | h = −10→10 |
Tmin = 0.946, Tmax = 0.963 | k = −11→11 |
16379 measured reflections | l = −12→12 |
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)] = 0.030 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.082 | H-atom parameters constrained |
S = 1.08 | w = 1/[σ2(Fo2) + (0.0423P)2 + 0.2206P] where P = (Fo2 + 2Fc2)/3 |
2769 reflections | (Δ/σ)max = 0.001 |
220 parameters | Δρmax = 0.15 e Å−3 |
0 restraints | Δρmin = −0.24 e Å−3 |
C18H12O6 | γ = 68.655 (1)° |
Mr = 324.28 | V = 786.65 (3) Å3 |
Triclinic, P1 | Z = 2 |
a = 8.5765 (2) Å | Mo Kα radiation |
b = 9.8469 (2) Å | µ = 0.10 mm−1 |
c = 10.2677 (2) Å | T = 100 K |
α = 78.903 (1)° | 0.54 × 0.43 × 0.37 mm |
β = 79.552 (1)° |
Bruker APEXII CCD diffractometer | 2769 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 2004) | 2558 reflections with I > 2σ(I) |
Tmin = 0.946, Tmax = 0.963 | Rint = 0.022 |
16379 measured reflections |
R[F2 > 2σ(F2)] = 0.030 | 0 restraints |
wR(F2) = 0.082 | H-atom parameters constrained |
S = 1.08 | Δρmax = 0.15 e Å−3 |
2769 reflections | Δρmin = −0.24 e Å−3 |
220 parameters |
Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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 | 0.83566 (10) | 0.52293 (9) | 0.16775 (8) | 0.0236 (2) | |
O2 | 0.57685 (10) | 0.57849 (10) | 0.28339 (8) | 0.0293 (2) | |
O3 | 0.65384 (9) | 0.22546 (9) | 1.31248 (7) | 0.02084 (19) | |
O4 | 0.41386 (10) | 0.31372 (9) | 1.21571 (8) | 0.0268 (2) | |
O5 | 1.77215 (9) | −0.03869 (9) | 0.67379 (8) | 0.0236 (2) | |
O6 | 1.70937 (10) | −0.04808 (10) | 0.89660 (8) | 0.0299 (2) | |
C1 | 0.75769 (16) | 0.59765 (14) | 0.04628 (11) | 0.0278 (3) | |
H1A | 0.6774 | 0.5528 | 0.0338 | 0.042* | |
H1B | 0.8452 | 0.5882 | −0.0308 | 0.042* | |
H1C | 0.6982 | 0.7021 | 0.0544 | 0.042* | |
C2 | 0.72764 (14) | 0.52404 (12) | 0.27834 (11) | 0.0190 (2) | |
C3 | 0.81227 (13) | 0.45041 (12) | 0.39566 (11) | 0.0194 (2) | |
C4 | 0.86741 (13) | 0.38829 (12) | 0.49835 (11) | 0.0185 (2) | |
C5 | 0.55244 (15) | 0.23382 (15) | 1.44175 (11) | 0.0278 (3) | |
H5A | 0.4759 | 0.3352 | 1.4466 | 0.042* | |
H5B | 0.6263 | 0.2036 | 1.5123 | 0.042* | |
H5C | 0.4865 | 0.1683 | 1.4539 | 0.042* | |
C6 | 0.56511 (13) | 0.26911 (12) | 1.20822 (11) | 0.0188 (2) | |
C7 | 0.67830 (14) | 0.25513 (12) | 1.08442 (11) | 0.0203 (2) | |
C8 | 0.77122 (13) | 0.24785 (11) | 0.98194 (11) | 0.0188 (2) | |
C9 | 1.94875 (14) | −0.09886 (14) | 0.69328 (13) | 0.0277 (3) | |
H9A | 1.9750 | −0.0336 | 0.7404 | 0.042* | |
H9B | 2.0182 | −0.1071 | 0.6062 | 0.042* | |
H9C | 1.9726 | −0.1965 | 0.7465 | 0.042* | |
C10 | 1.66647 (14) | −0.01980 (12) | 0.78696 (11) | 0.0190 (2) | |
C11 | 1.49194 (13) | 0.04128 (12) | 0.76135 (10) | 0.0193 (2) | |
C12 | 1.34504 (14) | 0.09501 (12) | 0.74997 (10) | 0.0183 (2) | |
C13 | 0.93204 (13) | 0.31191 (12) | 0.62162 (11) | 0.0175 (2) | |
C14 | 0.82157 (13) | 0.31487 (12) | 0.73950 (11) | 0.0183 (2) | |
H14 | 0.7041 | 0.3661 | 0.7379 | 0.022* | |
C15 | 0.88415 (13) | 0.24233 (12) | 0.85995 (11) | 0.0178 (2) | |
C16 | 1.05675 (14) | 0.16784 (12) | 0.86244 (11) | 0.0180 (2) | |
H16 | 1.0992 | 0.1189 | 0.9445 | 0.022* | |
C17 | 1.16685 (13) | 0.16532 (11) | 0.74421 (11) | 0.0171 (2) | |
C18 | 1.10490 (13) | 0.23615 (12) | 0.62325 (11) | 0.0178 (2) | |
H18 | 1.1797 | 0.2329 | 0.5425 | 0.021* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0233 (4) | 0.0293 (4) | 0.0145 (4) | −0.0059 (3) | −0.0046 (3) | 0.0018 (3) |
O2 | 0.0194 (5) | 0.0351 (5) | 0.0271 (5) | −0.0035 (4) | −0.0074 (3) | 0.0034 (4) |
O3 | 0.0171 (4) | 0.0290 (4) | 0.0140 (4) | −0.0066 (3) | −0.0007 (3) | −0.0010 (3) |
O4 | 0.0179 (4) | 0.0345 (5) | 0.0225 (4) | −0.0033 (4) | −0.0029 (3) | −0.0018 (3) |
O5 | 0.0146 (4) | 0.0310 (4) | 0.0222 (4) | −0.0039 (3) | −0.0028 (3) | −0.0036 (3) |
O6 | 0.0230 (4) | 0.0434 (5) | 0.0209 (5) | −0.0074 (4) | −0.0089 (3) | −0.0005 (4) |
C1 | 0.0363 (7) | 0.0292 (6) | 0.0153 (6) | −0.0082 (5) | −0.0099 (5) | 0.0038 (5) |
C2 | 0.0204 (6) | 0.0181 (5) | 0.0186 (6) | −0.0061 (4) | −0.0053 (4) | −0.0007 (4) |
C3 | 0.0162 (5) | 0.0209 (5) | 0.0196 (6) | −0.0046 (4) | −0.0020 (4) | −0.0025 (4) |
C4 | 0.0153 (5) | 0.0205 (5) | 0.0185 (6) | −0.0050 (4) | −0.0015 (4) | −0.0026 (4) |
C5 | 0.0248 (6) | 0.0411 (7) | 0.0133 (5) | −0.0097 (5) | 0.0017 (4) | −0.0005 (5) |
C6 | 0.0191 (6) | 0.0179 (5) | 0.0177 (5) | −0.0050 (4) | −0.0023 (4) | −0.0009 (4) |
C7 | 0.0203 (6) | 0.0211 (6) | 0.0187 (6) | −0.0059 (4) | −0.0048 (5) | −0.0008 (4) |
C8 | 0.0186 (5) | 0.0191 (5) | 0.0178 (6) | −0.0052 (4) | −0.0042 (4) | −0.0012 (4) |
C9 | 0.0139 (5) | 0.0309 (6) | 0.0358 (7) | −0.0024 (5) | −0.0033 (5) | −0.0090 (5) |
C10 | 0.0176 (5) | 0.0185 (5) | 0.0203 (6) | −0.0055 (4) | −0.0049 (4) | −0.0002 (4) |
C11 | 0.0194 (6) | 0.0225 (6) | 0.0149 (5) | −0.0070 (5) | −0.0035 (4) | 0.0008 (4) |
C12 | 0.0200 (6) | 0.0201 (5) | 0.0151 (5) | −0.0076 (4) | −0.0034 (4) | −0.0003 (4) |
C13 | 0.0175 (5) | 0.0185 (5) | 0.0163 (5) | −0.0057 (4) | −0.0044 (4) | −0.0009 (4) |
C14 | 0.0147 (5) | 0.0193 (5) | 0.0199 (6) | −0.0039 (4) | −0.0037 (4) | −0.0026 (4) |
C15 | 0.0184 (5) | 0.0190 (5) | 0.0166 (5) | −0.0071 (4) | −0.0020 (4) | −0.0024 (4) |
C16 | 0.0204 (6) | 0.0188 (5) | 0.0157 (5) | −0.0073 (4) | −0.0055 (4) | −0.0005 (4) |
C17 | 0.0156 (5) | 0.0174 (5) | 0.0188 (5) | −0.0053 (4) | −0.0046 (4) | −0.0015 (4) |
C18 | 0.0166 (5) | 0.0207 (5) | 0.0162 (5) | −0.0070 (4) | −0.0013 (4) | −0.0021 (4) |
O1—C2 | 1.3280 (14) | C6—C7 | 1.4490 (15) |
O1—C1 | 1.4612 (13) | C7—C8 | 1.1961 (16) |
O2—C2 | 1.2018 (14) | C8—C15 | 1.4345 (15) |
O3—C6 | 1.3379 (13) | C9—H9A | 0.9800 |
O3—C5 | 1.4478 (13) | C9—H9B | 0.9800 |
O4—C6 | 1.2015 (13) | C9—H9C | 0.9800 |
O5—C10 | 1.3359 (13) | C10—C11 | 1.4485 (15) |
O5—C9 | 1.4478 (13) | C11—C12 | 1.1938 (16) |
O6—C10 | 1.1980 (14) | C12—C17 | 1.4371 (15) |
C1—H1A | 0.9800 | C13—C14 | 1.3931 (15) |
C1—H1B | 0.9800 | C13—C18 | 1.3978 (15) |
C1—H1C | 0.9800 | C14—C15 | 1.3963 (15) |
C2—C3 | 1.4496 (15) | C14—H14 | 0.9500 |
C3—C4 | 1.1965 (16) | C15—C16 | 1.3950 (15) |
C4—C13 | 1.4351 (15) | C16—C17 | 1.3945 (15) |
C5—H5A | 0.9800 | C16—H16 | 0.9500 |
C5—H5B | 0.9800 | C17—C18 | 1.3955 (15) |
C5—H5C | 0.9800 | C18—H18 | 0.9500 |
C2—O1—C1 | 114.65 (9) | H9A—C9—H9B | 109.5 |
C6—O3—C5 | 114.53 (8) | O5—C9—H9C | 109.5 |
C10—O5—C9 | 114.15 (9) | H9A—C9—H9C | 109.5 |
O1—C1—H1A | 109.5 | H9B—C9—H9C | 109.5 |
O1—C1—H1B | 109.5 | O6—C10—O5 | 124.66 (10) |
H1A—C1—H1B | 109.5 | O6—C10—C11 | 123.62 (10) |
O1—C1—H1C | 109.5 | O5—C10—C11 | 111.72 (9) |
H1A—C1—H1C | 109.5 | C12—C11—C10 | 174.86 (11) |
H1B—C1—H1C | 109.5 | C11—C12—C17 | 175.86 (11) |
O2—C2—O1 | 125.16 (10) | C14—C13—C18 | 120.36 (10) |
O2—C2—C3 | 122.68 (10) | C14—C13—C4 | 119.56 (9) |
O1—C2—C3 | 112.16 (9) | C18—C13—C4 | 120.08 (10) |
C4—C3—C2 | 173.59 (11) | C13—C14—C15 | 119.76 (10) |
C3—C4—C13 | 178.97 (12) | C13—C14—H14 | 120.1 |
O3—C5—H5A | 109.5 | C15—C14—H14 | 120.1 |
O3—C5—H5B | 109.5 | C16—C15—C14 | 120.15 (10) |
H5A—C5—H5B | 109.5 | C16—C15—C8 | 119.93 (10) |
O3—C5—H5C | 109.5 | C14—C15—C8 | 119.90 (10) |
H5A—C5—H5C | 109.5 | C17—C16—C15 | 119.89 (10) |
H5B—C5—H5C | 109.5 | C17—C16—H16 | 120.1 |
O4—C6—O3 | 125.17 (10) | C15—C16—H16 | 120.1 |
O4—C6—C7 | 124.83 (10) | C16—C17—C18 | 120.25 (9) |
O3—C6—C7 | 110.00 (9) | C16—C17—C12 | 119.01 (9) |
C8—C7—C6 | 178.08 (11) | C18—C17—C12 | 120.67 (10) |
C7—C8—C15 | 178.35 (11) | C17—C18—C13 | 119.58 (10) |
O5—C9—H9A | 109.5 | C17—C18—H18 | 120.2 |
O5—C9—H9B | 109.5 | C13—C18—H18 | 120.2 |
C1—O1—C2—O2 | 1.09 (16) | C13—C14—C15—C8 | 178.64 (10) |
C1—O1—C2—C3 | −179.11 (9) | C14—C15—C16—C17 | −0.29 (16) |
C5—O3—C6—O4 | 0.66 (16) | C8—C15—C16—C17 | −178.57 (9) |
C5—O3—C6—C7 | −179.49 (9) | C15—C16—C17—C18 | −0.46 (16) |
C9—O5—C10—O6 | 0.41 (16) | C15—C16—C17—C12 | 176.57 (9) |
C9—O5—C10—C11 | 179.68 (9) | C16—C17—C18—C13 | 1.13 (15) |
C18—C13—C14—C15 | 0.32 (16) | C12—C17—C18—C13 | −175.85 (10) |
C4—C13—C14—C15 | −179.16 (10) | C14—C13—C18—C17 | −1.06 (16) |
C13—C14—C15—C16 | 0.35 (16) | C4—C13—C18—C17 | 178.42 (10) |
Cg1 is the centroid of the C13–C18 ring and Cg3 is the mid-point of atoms C7 and C8. |
D—H···A | D—H | H···A | D···A | D—H···A |
C1—H1C···O6i | 0.98 | 2.70 | 3.4378 (15) | 133 |
C5—H5B···O5ii | 0.98 | 2.66 | 3.4517 (15) | 138 |
C14—H14···O2iii | 0.95 | 2.31 | 3.2278 (13) | 162 |
C16—H16···O6iv | 0.95 | 2.35 | 3.2390 (13) | 155 |
C1—H1A···Cg3v | 0.98 | 2.85 | 3.5506 (13) | 130 |
C9—H9A···Cg1vi | 0.98 | 2.76 | 3.6302 (13) | 148 |
Symmetry codes: (i) x−1, y+1, z−1; (ii) x−1, y, z+1; (iii) −x+1, −y+1, −z+1; (iv) −x+3, −y, −z+2; (v) x, y, z−1; (vi) x+1, y, z. |
Cg1 is the centroid of the C13–C18 ring and Cg3 is the mid-point of atoms C7 and C8. |
D—H···A | D—H | H···A | D···A | D—H···A |
C1—H1C···O6i | 0.98 | 2.70 | 3.4378 (15) | 132.8 |
C5—H5B···O5ii | 0.98 | 2.66 | 3.4517 (15) | 138.3 |
C14—H14···O2iii | 0.95 | 2.31 | 3.2278 (13) | 162.0 |
C16—H16···O6iv | 0.95 | 2.35 | 3.2390 (13) | 154.7 |
C1—H1A···Cg3v | 0.98 | 2.85 | 3.5506 (13) | 129.5 |
C9—H9A···Cg1vi | 0.98 | 2.76 | 3.6302 (13) | 148.3 |
Symmetry codes: (i) x−1, y+1, z−1; (ii) x−1, y, z+1; (iii) −x+1, −y+1, −z+1; (iv) −x+3, −y, −z+2; (v) x, y, z−1; (vi) x+1, y, z. |
Experimental details
Crystal data | |
Chemical formula | C18H12O6 |
Mr | 324.28 |
Crystal system, space group | Triclinic, P1 |
Temperature (K) | 100 |
a, b, c (Å) | 8.5765 (2), 9.8469 (2), 10.2677 (2) |
α, β, γ (°) | 78.903 (1), 79.552 (1), 68.655 (1) |
V (Å3) | 786.65 (3) |
Z | 2 |
Radiation type | Mo Kα |
µ (mm−1) | 0.10 |
Crystal size (mm) | 0.54 × 0.43 × 0.37 |
Data collection | |
Diffractometer | Bruker APEXII CCD |
Absorption correction | Multi-scan (SADABS; Sheldrick, 2004) |
Tmin, Tmax | 0.946, 0.963 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 16379, 2769, 2558 |
Rint | 0.022 |
(sin θ/λ)max (Å−1) | 0.595 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.030, 0.082, 1.08 |
No. of reflections | 2769 |
No. of parameters | 220 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.15, −0.24 |
Computer programs: APEX2 (Bruker, 2008), SAINT (Bruker, 2008), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).
Acknowledgements
This work was supported by the Deutsche Forschungsgemeinschaft (DFG) under the program SPP 1362/1.
References
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The title compound, C18H12O6, is an interesting synthetic intermediate for the preparation of application–oriented solid materials involving both porous coordination polymers (MacGillivray, 2010) or metal-organic frameworks (Noro & Kitagawa, 2010) and crystalline inclusion hosts (Weber, 1996; Katzsch et al., 2016). In the structure of the molecule (Fig. 1), the alkyne bonds are distorted which is shown by the corresponding bond angles [C2-C3-C4 173.6 (1)°, C3-C4-C13 179.0 (1)°, C6-C7-C8 178.1 (1)°, C7-C8-C15 178.4 (1)°, C10-C11-C12 174.9 (1)°, C11-C12-C17 175.9 (1)°] and the ester functions are not arranged in the benzene plane [interplanar angles: 3.5° (C2, O1, O2), 13.8° (C6, O3, O4), 14.5° (C10, O5, O10)]. The molecules are connected in layers parallel to the (131)-plane by weak C-H···O hydrogen bonds (Desiraju & Steiner, 1999) (Table 1) giving rise to new hydrogen bond ring motifs with the graph sets R22(14) and R44(22) (Fig. 2). The layers are stabilized among each other also by weak C-H···O hydrogen bonds [d(C1···O6) 3.438 (1) Å] and additionally by C-H···π contacts (Desiraju & Steiner, 1999) [d(C1···Cg3) 3.551 (1) Å d(C9···Cg1) 3.630 (1) Å].