Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680502951X/wn6378sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S160053680502951X/wn6378Isup2.hkl |
CCDC reference: 287747
Key indicators
- Single-crystal X-ray study
- T = 294 K
- Mean (C-C)= 0.002 Å
- R factor = 0.036
- wR factor = 0.101
- Data-to-parameter ratio = 13.7
checkCIF/PLATON results
No syntax errors found No errors found in this datablock
To a solution of 4-hydroxy-3-methoxybenzaldehyde (15.2 g, 10 mmol) and potassium carbonate (13.8 g, 10 mmol) in acetonitrile (500 ml), 1,4-dibromobutane (10.8 g, 5 mmol) was added over a period of 30 min and the mixture refluxed for 24 h under nitrogen. The solvent was removed and the resultant oil poured into ice–water (500 ml). The white precipitate was then isolated and recrystallized from ethanol to give the pure compound in 63% yield. Colorless single crystals of (I) suitable for X-ray analysis were obtained by slow evaporation of an acetonitrile solution.
H atoms were included in calculated positions and refined using a riding-model approximation; C—H = 0.93 (aromatic), 0.96 (methyl) and 0.97 Å (methylene), and Uiso(H) = xUeq(C), where x = 1.5 for methyl and 1.2 for other H atoms.
Data collection: SMART (Bruker, 1999); cell refinement: SAINT (Bruker, 1999); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1999); software used to prepare material for publication: SHELXTL.
Fig. 1. The structure of (I), with displacement ellipsoids for non-H atoms drawn at the 30% probability level. [Symmetry code: (i) −x, −y, 2 − z.] |
C20H22O6 | F(000) = 380 |
Mr = 358.38 | Dx = 1.282 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -p 2ybc | Cell parameters from 1740 reflections |
a = 7.4200 (16) Å | θ = 2.8–26.3° |
b = 7.6630 (16) Å | µ = 0.10 mm−1 |
c = 16.407 (3) Å | T = 294 K |
β = 95.787 (4)° | Block, colorless |
V = 928.2 (3) Å3 | 0.36 × 0.30 × 0.24 mm |
Z = 2 |
Bruker SMART APEX CCD area-detector diffractometer | 1632 independent reflections |
Radiation source: fine-focus sealed tube | 1142 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.028 |
ϕ and ω scans | θmax = 25.0°, θmin = 2.5° |
Absorption correction: multi-scan (SADABS; Bruker, 1999) | h = −8→7 |
Tmin = 0.944, Tmax = 0.977 | k = −9→8 |
4527 measured reflections | l = −14→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)] = 0.036 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.101 | H-atom parameters constrained |
S = 1.04 | w = 1/[σ2(Fo2) + (0.0429P)2 + 0.2073P] where P = (Fo2 + 2Fc2)/3 |
1632 reflections | (Δ/σ)max = 0.001 |
119 parameters | Δρmax = 0.14 e Å−3 |
6 restraints | Δρmin = −0.14 e Å−3 |
C20H22O6 | V = 928.2 (3) Å3 |
Mr = 358.38 | Z = 2 |
Monoclinic, P21/c | Mo Kα radiation |
a = 7.4200 (16) Å | µ = 0.10 mm−1 |
b = 7.6630 (16) Å | T = 294 K |
c = 16.407 (3) Å | 0.36 × 0.30 × 0.24 mm |
β = 95.787 (4)° |
Bruker SMART APEX CCD area-detector diffractometer | 1632 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 1999) | 1142 reflections with I > 2σ(I) |
Tmin = 0.944, Tmax = 0.977 | Rint = 0.028 |
4527 measured reflections |
R[F2 > 2σ(F2)] = 0.036 | 6 restraints |
wR(F2) = 0.101 | H-atom parameters constrained |
S = 1.04 | Δρmax = 0.14 e Å−3 |
1632 reflections | Δρmin = −0.14 e Å−3 |
119 parameters |
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. |
x | y | z | Uiso*/Ueq | ||
O1 | 0.34776 (14) | 0.12609 (14) | 0.93658 (7) | 0.0478 (3) | |
O2 | 0.58088 (16) | 0.37044 (15) | 0.93058 (8) | 0.0561 (4) | |
O3 | 0.9952 (2) | 0.1593 (2) | 0.70978 (12) | 0.1046 (6) | |
C1 | 0.4770 (2) | 0.0965 (2) | 0.88525 (9) | 0.0394 (4) | |
C2 | 0.4892 (2) | −0.0514 (2) | 0.83826 (10) | 0.0502 (5) | |
H2 | 0.4070 | −0.1421 | 0.8416 | 0.060* | |
C3 | 0.6242 (2) | −0.0645 (2) | 0.78607 (11) | 0.0529 (5) | |
H3 | 0.6323 | −0.1647 | 0.7547 | 0.063* | |
C4 | 0.7463 (2) | 0.0687 (2) | 0.78007 (10) | 0.0463 (4) | |
C5 | 0.7368 (2) | 0.2177 (2) | 0.82858 (10) | 0.0440 (4) | |
H5 | 0.8201 | 0.3074 | 0.8252 | 0.053* | |
C6 | 0.6049 (2) | 0.2321 (2) | 0.88113 (9) | 0.0389 (4) | |
C7 | 0.7032 (3) | 0.5134 (2) | 0.92870 (14) | 0.0750 (7) | |
H7A | 0.8244 | 0.4739 | 0.9446 | 0.112* | |
H7B | 0.6715 | 0.6021 | 0.9660 | 0.112* | |
H7C | 0.6961 | 0.5604 | 0.8742 | 0.112* | |
C8 | 0.8809 (3) | 0.0528 (3) | 0.72112 (13) | 0.0650 (6) | |
H8 | 0.8778 | −0.0483 | 0.6897 | 0.078* | |
C9 | 0.2067 (2) | −0.0015 (2) | 0.93851 (10) | 0.0452 (4) | |
H9A | 0.2574 | −0.1129 | 0.9573 | 0.054* | |
H9B | 0.1441 | −0.0171 | 0.8842 | 0.054* | |
C10 | 0.0776 (2) | 0.0643 (2) | 0.99644 (10) | 0.0446 (4) | |
H10A | 0.0284 | 0.1758 | 0.9771 | 0.054* | |
H10B | 0.1426 | 0.0822 | 1.0501 | 0.054* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0405 (6) | 0.0500 (7) | 0.0558 (7) | −0.0139 (5) | 0.0190 (5) | −0.0081 (6) |
O2 | 0.0567 (8) | 0.0428 (7) | 0.0740 (9) | −0.0145 (6) | 0.0326 (6) | −0.0130 (6) |
O3 | 0.0961 (12) | 0.1047 (13) | 0.1261 (15) | −0.0170 (11) | 0.0760 (11) | −0.0200 (11) |
C1 | 0.0348 (9) | 0.0451 (9) | 0.0387 (8) | −0.0023 (7) | 0.0059 (7) | −0.0001 (7) |
C2 | 0.0454 (10) | 0.0517 (11) | 0.0542 (10) | −0.0114 (8) | 0.0085 (8) | −0.0097 (9) |
C3 | 0.0504 (10) | 0.0572 (11) | 0.0511 (10) | 0.0007 (9) | 0.0051 (8) | −0.0161 (9) |
C4 | 0.0404 (10) | 0.0551 (11) | 0.0444 (9) | 0.0059 (8) | 0.0086 (7) | −0.0004 (8) |
C5 | 0.0381 (9) | 0.0454 (10) | 0.0499 (10) | −0.0017 (7) | 0.0119 (7) | 0.0049 (8) |
C6 | 0.0375 (8) | 0.0380 (9) | 0.0425 (9) | −0.0004 (7) | 0.0096 (7) | 0.0004 (7) |
C7 | 0.0745 (15) | 0.0467 (11) | 0.1113 (18) | −0.0223 (10) | 0.0469 (13) | −0.0203 (11) |
C8 | 0.0601 (13) | 0.0738 (14) | 0.0649 (13) | 0.0110 (11) | 0.0245 (10) | −0.0058 (11) |
C9 | 0.0369 (9) | 0.0501 (10) | 0.0491 (10) | −0.0144 (8) | 0.0069 (7) | 0.0000 (8) |
C10 | 0.0368 (9) | 0.0478 (10) | 0.0497 (10) | −0.0083 (8) | 0.0063 (7) | 0.0027 (8) |
O1—C1 | 1.3578 (18) | C5—C6 | 1.372 (2) |
O1—C9 | 1.4353 (18) | C5—H5 | 0.9300 |
O2—C6 | 1.3575 (18) | C7—H7A | 0.9600 |
O2—C7 | 1.425 (2) | C7—H7B | 0.9600 |
O3—C8 | 1.205 (2) | C7—H7C | 0.9600 |
C1—C2 | 1.379 (2) | C8—H8 | 0.9300 |
C1—C6 | 1.414 (2) | C9—C10 | 1.503 (2) |
C2—C3 | 1.386 (2) | C9—H9A | 0.9700 |
C2—H2 | 0.9300 | C9—H9B | 0.9700 |
C3—C4 | 1.375 (2) | C10—C10i | 1.529 (3) |
C3—H3 | 0.9300 | C10—H10A | 0.9700 |
C4—C5 | 1.397 (2) | C10—H10B | 0.9700 |
C4—C8 | 1.463 (2) | ||
C1—O1—C9 | 117.53 (12) | O2—C7—H7B | 109.5 |
C6—O2—C7 | 117.70 (13) | H7A—C7—H7B | 109.5 |
O1—C1—C2 | 125.06 (14) | O2—C7—H7C | 109.5 |
O1—C1—C6 | 115.24 (14) | H7A—C7—H7C | 109.5 |
C2—C1—C6 | 119.70 (15) | H7B—C7—H7C | 109.5 |
C1—C2—C3 | 119.82 (16) | O3—C8—C4 | 125.7 (2) |
C1—C2—H2 | 120.1 | O3—C8—H8 | 117.2 |
C3—C2—H2 | 120.1 | C4—C8—H8 | 117.2 |
C4—C3—C2 | 120.89 (16) | O1—C9—C10 | 107.33 (13) |
C4—C3—H3 | 119.6 | O1—C9—H9A | 110.2 |
C2—C3—H3 | 119.6 | C10—C9—H9A | 110.2 |
C3—C4—C5 | 119.59 (15) | O1—C9—H9B | 110.2 |
C3—C4—C8 | 118.92 (17) | C10—C9—H9B | 110.2 |
C5—C4—C8 | 121.46 (17) | H9A—C9—H9B | 108.5 |
C6—C5—C4 | 120.29 (15) | C9—C10—C10i | 111.39 (17) |
C6—C5—H5 | 119.9 | C9—C10—H10A | 109.4 |
C4—C5—H5 | 119.9 | C10i—C10—H10A | 109.4 |
O2—C6—C5 | 125.71 (14) | C9—C10—H10B | 109.4 |
O2—C6—C1 | 114.59 (13) | C10i—C10—H10B | 109.4 |
C5—C6—C1 | 119.69 (15) | H10A—C10—H10B | 108.0 |
O2—C7—H7A | 109.5 | ||
C9—O1—C1—C2 | −3.9 (2) | C4—C5—C6—O2 | −179.35 (15) |
C9—O1—C1—C6 | 175.47 (14) | C4—C5—C6—C1 | −0.8 (2) |
O1—C1—C2—C3 | 177.96 (16) | O1—C1—C6—O2 | 1.2 (2) |
C6—C1—C2—C3 | −1.4 (2) | C2—C1—C6—O2 | −179.37 (14) |
C1—C2—C3—C4 | −0.3 (3) | O1—C1—C6—C5 | −177.45 (14) |
C2—C3—C4—C5 | 1.4 (3) | C2—C1—C6—C5 | 2.0 (2) |
C2—C3—C4—C8 | −176.95 (17) | C3—C4—C8—O3 | −179.9 (2) |
C3—C4—C5—C6 | −0.8 (2) | C5—C4—C8—O3 | 1.7 (3) |
C8—C4—C5—C6 | 177.51 (16) | C1—O1—C9—C10 | −177.51 (13) |
C7—O2—C6—C5 | −0.5 (2) | O1—C9—C10—C10i | −179.36 (16) |
C7—O2—C6—C1 | −179.06 (16) |
Symmetry code: (i) −x, −y, −z+2. |
Experimental details
Crystal data | |
Chemical formula | C20H22O6 |
Mr | 358.38 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 294 |
a, b, c (Å) | 7.4200 (16), 7.6630 (16), 16.407 (3) |
β (°) | 95.787 (4) |
V (Å3) | 928.2 (3) |
Z | 2 |
Radiation type | Mo Kα |
µ (mm−1) | 0.10 |
Crystal size (mm) | 0.36 × 0.30 × 0.24 |
Data collection | |
Diffractometer | Bruker SMART APEX CCD area-detector diffractometer |
Absorption correction | Multi-scan (SADABS; Bruker, 1999) |
Tmin, Tmax | 0.944, 0.977 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 4527, 1632, 1142 |
Rint | 0.028 |
(sin θ/λ)max (Å−1) | 0.595 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.036, 0.101, 1.04 |
No. of reflections | 1632 |
No. of parameters | 119 |
No. of restraints | 6 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.14, −0.14 |
Computer programs: SMART (Bruker, 1999), SAINT (Bruker, 1999), SAINT, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL (Bruker, 1999), SHELXTL.
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Crystal engineering plays an important role in the preparation of crystalline solid materials, enabling their architecture and properties to be predictable (Parashar et al., 1988; Tynan et al., 2005). We are interested in the molecular and ionic recognition of crown ethers. As part of this study, we report the synthesis and structure of the title compound, (I), which will provide useful information on its physical and chemical properties.
A view of the molecule is shown in Fig. 1. A crystallographic center of symmetry is located at the mid-point of the C10—C10i bond [symmetry code: (i) −x, −y, 2 − z]. The vanillin moiety (C1–C8/O1–O3) is planar, with an r.m.s. deviation for fitted atoms of 0.0289 Å. The chain of atoms C9—C10—C10i—C9i linking the two vanillin systems is planar and this plane makes a dihedral angle of 5.2 (2)° with the vanillin plane. The two aromatic rings in the molecule are parallel to each other. The bond lengths and angles are unexceptional.