organic compounds
The molecules of the title compound, C13H14O4, the condensation product of vanillin and acetylacetone, are hydrogen bonded into a linear chain arising from interaction between the hydroxy group of one molecule and the acetyl group of an adjacent molecule.
Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805002941/is6044sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536805002941/is6044Isup2.hkl |
CCDC reference: 269791
Computing details top
Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPII (Johnson, 1976); software used to prepare material for publication: SHELXL97.
3-[(4-Hydroxy-3-methoxyphenyl)methylene]-2,4-pentanedione top
Crystal data top
C13H14O4 | F(000) = 992 |
Mr = 234.24 | Dx = 1.295 Mg m−3 |
Monoclinic, C2/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -C 2yc | Cell parameters from 1017 reflections |
a = 20.792 (3) Å | θ = 2.7–27.0° |
b = 8.247 (1) Å | µ = 0.10 mm−1 |
c = 15.097 (2) Å | T = 295 K |
β = 111.778 (2)° | Block, yellow |
V = 2403.7 (5) Å3 | 0.50 × 0.41 × 0.21 mm |
Z = 8 |
Data collection top
Bruker SMART area-detector diffractometer | 2139 reflections with I > 2σ(I) |
Radiation source: medium-focus sealed tube | Rint = 0.013 |
Graphite monochromator | θmax = 27.1°, θmin = 2.1° |
φ and ω scans | h = −23→26 |
7252 measured reflections | k = −10→6 |
2649 independent reflections | l = −19→19 |
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)] = 0.041 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.137 | H-atom parameters constrained |
S = 1.01 | w = 1/[σ2(Fo2) + (0.0809P)2 + 0.8642P] where P = (Fo2 + 2Fc2)/3 |
2649 reflections | (Δ/σ)max = 0.001 |
158 parameters | Δρmax = 0.18 e Å−3 |
0 restraints | Δρmin = −0.15 e Å−3 |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
x | y | z | Uiso*/Ueq | ||
O1 | 0.2366 (1) | 0.6901 (2) | 0.6869 (1) | 0.0752 (4) | |
O2 | 0.0720 (1) | 0.7002 (2) | 0.5236 (1) | 0.0717 (4) | |
O3 | 0.4270 (1) | 0.3703 (2) | 0.4380 (1) | 0.0580 (3) | |
O4 | 0.4768 (1) | 0.2309 (2) | 0.6091 (1) | 0.0614 (3) | |
C1 | 0.1596 (1) | 0.4766 (3) | 0.6798 (1) | 0.0759 (5) | |
C2 | 0.1949 (1) | 0.5934 (2) | 0.6382 (1) | 0.0473 (3) | |
C3 | 0.1766 (1) | 0.5916 (2) | 0.5321 (1) | 0.0410 (3) | |
C4 | 0.1072 (1) | 0.6590 (2) | 0.4788 (1) | 0.0504 (3) | |
C5 | 0.0809 (1) | 0.6794 (3) | 0.3731 (1) | 0.0762 (6) | |
C6 | 0.2182 (1) | 0.5392 (2) | 0.4882 (1) | 0.0451 (3) | |
C7 | 0.2859 (1) | 0.4610 (2) | 0.5252 (1) | 0.0419 (3) | |
C8 | 0.3227 (1) | 0.4551 (2) | 0.4638 (1) | 0.0443 (3) | |
C9 | 0.3867 (1) | 0.3821 (2) | 0.4915 (1) | 0.0424 (3) | |
C10 | 0.4151 (1) | 0.3088 (2) | 0.5810 (1) | 0.0439 (3) | |
C11 | 0.3791 (1) | 0.3132 (2) | 0.6419 (1) | 0.0491 (3) | |
C12 | 0.3153 (1) | 0.3885 (2) | 0.6146 (1) | 0.0467 (3) | |
C13 | 0.4039 (1) | 0.4496 (2) | 0.3482 (1) | 0.0582 (4) | |
H4 | 0.4934 | 0.2380 | 0.5655 | 0.092* | |
H1a | 0.1780 | 0.3699 | 0.6796 | 0.114* | |
H1b | 0.1108 | 0.4765 | 0.6426 | 0.114* | |
H1c | 0.1672 | 0.5077 | 0.7442 | 0.114* | |
H5a | 0.0357 | 0.7278 | 0.3516 | 0.114* | |
H5b | 0.0781 | 0.5753 | 0.3434 | 0.114* | |
H5c | 0.1118 | 0.7481 | 0.3563 | 0.114* | |
H6 | 0.2008 | 0.5557 | 0.4226 | 0.054* | |
H8 | 0.3035 | 0.5013 | 0.4035 | 0.053* | |
H11 | 0.3981 | 0.2651 | 0.7018 | 0.059* | |
H12 | 0.2918 | 0.3907 | 0.6563 | 0.056* | |
H13a | 0.3611 | 0.4019 | 0.3070 | 0.087* | |
H13b | 0.4381 | 0.4379 | 0.3200 | 0.087* | |
H13c | 0.3968 | 0.5626 | 0.3567 | 0.087* |
Atomic displacement parameters (Å2) top
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0804 (8) | 0.0735 (8) | 0.0575 (7) | −0.0029 (6) | 0.0093 (6) | −0.0181 (6) |
O2 | 0.0539 (6) | 0.0953 (9) | 0.0761 (8) | 0.0270 (6) | 0.0361 (6) | 0.0040 (6) |
O3 | 0.0458 (5) | 0.0844 (8) | 0.0534 (6) | 0.0178 (5) | 0.0295 (5) | 0.0114 (5) |
O4 | 0.0475 (6) | 0.0842 (8) | 0.0561 (6) | 0.0260 (5) | 0.0235 (5) | 0.0125 (5) |
C1 | 0.091 (1) | 0.083 (1) | 0.069 (1) | 0.011 (1) | 0.047 (1) | 0.018 (1) |
C2 | 0.050 (1) | 0.049 (1) | 0.045 (1) | 0.014 (1) | 0.020 (1) | −0.003 (1) |
C3 | 0.038 (1) | 0.045 (1) | 0.043 (1) | 0.004 (1) | 0.017 (1) | −0.001 (1) |
C4 | 0.042 (1) | 0.057 (1) | 0.054 (1) | 0.010 (1) | 0.020 (1) | −0.001 (1) |
C5 | 0.059 (1) | 0.108 (2) | 0.055 (1) | 0.032 (1) | 0.012 (1) | 0.008 (1) |
C6 | 0.040 (1) | 0.057 (1) | 0.040 (1) | 0.007 (1) | 0.017 (1) | 0.001 (1) |
C7 | 0.038 (1) | 0.048 (1) | 0.043 (1) | 0.004 (1) | 0.019 (1) | −0.003 (1) |
C8 | 0.039 (1) | 0.055 (1) | 0.041 (1) | 0.006 (1) | 0.018 (1) | 0.003 (1) |
C9 | 0.038 (1) | 0.050 (1) | 0.044 (1) | 0.002 (1) | 0.021 (1) | −0.002 (1) |
C10 | 0.038 (1) | 0.049 (1) | 0.046 (1) | 0.007 (1) | 0.016 (1) | −0.002 (1) |
C11 | 0.051 (1) | 0.057 (1) | 0.042 (1) | 0.012 (1) | 0.021 (1) | 0.006 (1) |
C12 | 0.047 (1) | 0.055 (1) | 0.045 (1) | 0.009 (1) | 0.025 (1) | 0.001 (1) |
C13 | 0.062 (1) | 0.071 (1) | 0.054 (1) | 0.007 (1) | 0.035 (1) | 0.007 (1) |
Geometric parameters (Å, º) top
O1—C2 | 1.206 (2) | C11—C12 | 1.382 (2) |
O2—C4 | 1.215 (2) | O4—H4 | 0.85 |
O3—C9 | 1.366 (2) | C1—H1a | 0.96 |
O3—C13 | 1.419 (2) | C1—H1b | 0.96 |
O4—C10 | 1.354 (2) | C1—H1c | 0.96 |
C1—C2 | 1.484 (2) | C5—H5a | 0.96 |
C2—C3 | 1.503 (2) | C5—H5b | 0.96 |
C3—C6 | 1.342 (2) | C5—H5c | 0.96 |
C3—C4 | 1.477 (2) | C6—H6 | 0.93 |
C4—C5 | 1.492 (2) | C8—H8 | 0.93 |
C6—C7 | 1.458 (2) | C11—H11 | 0.93 |
C7—C12 | 1.392 (2) | C12—H12 | 0.93 |
C7—C8 | 1.405 (2) | C13—H13a | 0.96 |
C8—C9 | 1.376 (2) | C13—H13b | 0.96 |
C9—C10 | 1.396 (2) | C13—H13c | 0.96 |
C10—C11 | 1.385 (2) | ||
C9—O3—C13 | 117.9 (1) | C2—C1—H1b | 109.5 |
O1—C2—C1 | 121.9 (1) | H1a—C1—H1b | 109.5 |
O1—C2—C3 | 119.7 (1) | C2—C1—H1c | 109.5 |
C1—C2—C3 | 118.4 (1) | H1a—C1—H1c | 109.5 |
C4—C3—C6 | 122.1 (1) | H1b—C1—H1c | 109.5 |
C2—C3—C4 | 112.8 (1) | C4—C5—H5a | 109.5 |
C2—C3—C6 | 125.2 (1) | C4—C5—H5b | 109.5 |
O2—C4—C3 | 118.0 (1) | H5a—C5—H5b | 109.5 |
O2—C4—C5 | 120.5 (1) | C4—C5—H5c | 109.5 |
C3—C4—C5 | 121.5 (1) | H5a—C5—H5c | 109.5 |
C3—C6—C7 | 131.3 (1) | H5b—C5—H5c | 109.5 |
C6—C7—C12 | 125.2 (1) | C3—C6—H6 | 114.3 |
C8—C7—C12 | 118.2 (1) | C7—C6—H6 | 114.3 |
C6—C7—C8 | 116.5 (1) | C9—C8—H8 | 119.4 |
C7—C8—C9 | 121.1 (1) | C7—C8—H8 | 119.4 |
O3—C9—C8 | 126.0 (1) | C12—C11—H11 | 119.7 |
O3—C9—C10 | 114.1 (1) | C10—C11—H11 | 119.7 |
C8—C9—C10 | 119.9 (1) | C11—C12—H12 | 119.6 |
O4—C10—C11 | 119.1 (1) | C7—C12—H12 | 119.7 |
O4—C10—C9 | 121.4 (1) | O3—C13—H13a | 109.5 |
C9—C10—C11 | 119.5 (1) | O3—C13—H13b | 109.5 |
C10—C11—C12 | 120.6 (1) | H13a—C13—H13b | 109.5 |
C7—C12—C11 | 120.7 (1) | O3—C13—H13c | 109.5 |
C10—O4—H4 | 109.5 | H13a—C13—H13c | 109.5 |
C2—C1—H1a | 109.5 | H13b—C13—H13c | 109.5 |
O1—C2—C3—C6 | 71.9 (2) | C13—O3—C9—C8 | 4.7 (2) |
C1—C2—C3—C6 | −109.3 (2) | C13—O3—C9—C10 | −176.4 (1) |
O1—C2—C3—C4 | −106.5 (2) | C7—C8—C9—O3 | −179.6 (1) |
C1—C2—C3—C4 | 72.4 (2) | C7—C8—C9—C10 | 1.6 (2) |
O2—C4—C3—C6 | 178.3 (2) | O3—C9—C10—O4 | −1.3 (2) |
C2—C3—C4—O2 | −3.3 (2) | C8—C9—C10—O4 | 177.6 (1) |
C6—C3—C4—C5 | −2.8 (2) | O3—C9—C10—C11 | 179.8 (1) |
C2—C3—C4—C5 | 175.6 (2) | C8—C9—C10—C11 | −1.3 (2) |
C4—C3—C6—C7 | −176.0 (1) | O4—C10—C11—C12 | −178.5 (1) |
C2—C3—C6—C7 | 5.8 (3) | C9—C10—C11—C12 | 0.4 (2) |
C3—C6—C7—C12 | 16.3 (3) | C10—C11—C12—C7 | 0.1 (2) |
C3—C6—C7—C8 | −165.8 (2) | C8—C7—C12—C11 | 0.2 (2) |
C12—C7—C8—C9 | −1.0 (2) | C6—C7—C12—C11 | 178.1 (1) |
C6—C7—C8—C9 | −179.2 (1) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O4—H4···O2i | 0.85 | 1.98 | 2.746 (2) | 149 |
Symmetry code: (i) x+1/2, y−1/2, z. |