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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

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805002941/is6044sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536805002941/is6044Isup2.hkl
Contains datablock I

CCDC reference: 269791

Key indicators

  • Single-crystal X-ray study
  • T = 295 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.041
  • wR factor = 0.137
  • Data-to-parameter ratio = 16.8

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT152_ALERT_1_C Supplied and Calc Volume s.u. Inconsistent ..... ? PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C2
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 2 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 1 ALERT type 2 Indicator that the structure model may be wrong or deficient 0 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion

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
C13H14O4F(000) = 992
Mr = 234.24Dx = 1.295 Mg m3
Monoclinic, C2/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2ycCell parameters from 1017 reflections
a = 20.792 (3) Åθ = 2.7–27.0°
b = 8.247 (1) ŵ = 0.10 mm1
c = 15.097 (2) ÅT = 295 K
β = 111.778 (2)°Block, yellow
V = 2403.7 (5) Å30.50 × 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 tubeRint = 0.013
Graphite monochromatorθmax = 27.1°, θmin = 2.1°
φ and ω scansh = 2326
7252 measured reflectionsk = 106
2649 independent reflectionsl = 1919
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.041Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.137H-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 parametersΔρmax = 0.18 e Å3
0 restraintsΔρmin = 0.15 e Å3
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O10.2366 (1)0.6901 (2)0.6869 (1)0.0752 (4)
O20.0720 (1)0.7002 (2)0.5236 (1)0.0717 (4)
O30.4270 (1)0.3703 (2)0.4380 (1)0.0580 (3)
O40.4768 (1)0.2309 (2)0.6091 (1)0.0614 (3)
C10.1596 (1)0.4766 (3)0.6798 (1)0.0759 (5)
C20.1949 (1)0.5934 (2)0.6382 (1)0.0473 (3)
C30.1766 (1)0.5916 (2)0.5321 (1)0.0410 (3)
C40.1072 (1)0.6590 (2)0.4788 (1)0.0504 (3)
C50.0809 (1)0.6794 (3)0.3731 (1)0.0762 (6)
C60.2182 (1)0.5392 (2)0.4882 (1)0.0451 (3)
C70.2859 (1)0.4610 (2)0.5252 (1)0.0419 (3)
C80.3227 (1)0.4551 (2)0.4638 (1)0.0443 (3)
C90.3867 (1)0.3821 (2)0.4915 (1)0.0424 (3)
C100.4151 (1)0.3088 (2)0.5810 (1)0.0439 (3)
C110.3791 (1)0.3132 (2)0.6419 (1)0.0491 (3)
C120.3153 (1)0.3885 (2)0.6146 (1)0.0467 (3)
C130.4039 (1)0.4496 (2)0.3482 (1)0.0582 (4)
H40.49340.23800.56550.092*
H1a0.17800.36990.67960.114*
H1b0.11080.47650.64260.114*
H1c0.16720.50770.74420.114*
H5a0.03570.72780.35160.114*
H5b0.07810.57530.34340.114*
H5c0.11180.74810.35630.114*
H60.20080.55570.42260.054*
H80.30350.50130.40350.053*
H110.39810.26510.70180.059*
H120.29180.39070.65630.056*
H13a0.36110.40190.30700.087*
H13b0.43810.43790.32000.087*
H13c0.39680.56260.35670.087*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0804 (8)0.0735 (8)0.0575 (7)0.0029 (6)0.0093 (6)0.0181 (6)
O20.0539 (6)0.0953 (9)0.0761 (8)0.0270 (6)0.0361 (6)0.0040 (6)
O30.0458 (5)0.0844 (8)0.0534 (6)0.0178 (5)0.0295 (5)0.0114 (5)
O40.0475 (6)0.0842 (8)0.0561 (6)0.0260 (5)0.0235 (5)0.0125 (5)
C10.091 (1)0.083 (1)0.069 (1)0.011 (1)0.047 (1)0.018 (1)
C20.050 (1)0.049 (1)0.045 (1)0.014 (1)0.020 (1)0.003 (1)
C30.038 (1)0.045 (1)0.043 (1)0.004 (1)0.017 (1)0.001 (1)
C40.042 (1)0.057 (1)0.054 (1)0.010 (1)0.020 (1)0.001 (1)
C50.059 (1)0.108 (2)0.055 (1)0.032 (1)0.012 (1)0.008 (1)
C60.040 (1)0.057 (1)0.040 (1)0.007 (1)0.017 (1)0.001 (1)
C70.038 (1)0.048 (1)0.043 (1)0.004 (1)0.019 (1)0.003 (1)
C80.039 (1)0.055 (1)0.041 (1)0.006 (1)0.018 (1)0.003 (1)
C90.038 (1)0.050 (1)0.044 (1)0.002 (1)0.021 (1)0.002 (1)
C100.038 (1)0.049 (1)0.046 (1)0.007 (1)0.016 (1)0.002 (1)
C110.051 (1)0.057 (1)0.042 (1)0.012 (1)0.021 (1)0.006 (1)
C120.047 (1)0.055 (1)0.045 (1)0.009 (1)0.025 (1)0.001 (1)
C130.062 (1)0.071 (1)0.054 (1)0.007 (1)0.035 (1)0.007 (1)
Geometric parameters (Å, º) top
O1—C21.206 (2)C11—C121.382 (2)
O2—C41.215 (2)O4—H40.85
O3—C91.366 (2)C1—H1a0.96
O3—C131.419 (2)C1—H1b0.96
O4—C101.354 (2)C1—H1c0.96
C1—C21.484 (2)C5—H5a0.96
C2—C31.503 (2)C5—H5b0.96
C3—C61.342 (2)C5—H5c0.96
C3—C41.477 (2)C6—H60.93
C4—C51.492 (2)C8—H80.93
C6—C71.458 (2)C11—H110.93
C7—C121.392 (2)C12—H120.93
C7—C81.405 (2)C13—H13a0.96
C8—C91.376 (2)C13—H13b0.96
C9—C101.396 (2)C13—H13c0.96
C10—C111.385 (2)
C9—O3—C13117.9 (1)C2—C1—H1b109.5
O1—C2—C1121.9 (1)H1a—C1—H1b109.5
O1—C2—C3119.7 (1)C2—C1—H1c109.5
C1—C2—C3118.4 (1)H1a—C1—H1c109.5
C4—C3—C6122.1 (1)H1b—C1—H1c109.5
C2—C3—C4112.8 (1)C4—C5—H5a109.5
C2—C3—C6125.2 (1)C4—C5—H5b109.5
O2—C4—C3118.0 (1)H5a—C5—H5b109.5
O2—C4—C5120.5 (1)C4—C5—H5c109.5
C3—C4—C5121.5 (1)H5a—C5—H5c109.5
C3—C6—C7131.3 (1)H5b—C5—H5c109.5
C6—C7—C12125.2 (1)C3—C6—H6114.3
C8—C7—C12118.2 (1)C7—C6—H6114.3
C6—C7—C8116.5 (1)C9—C8—H8119.4
C7—C8—C9121.1 (1)C7—C8—H8119.4
O3—C9—C8126.0 (1)C12—C11—H11119.7
O3—C9—C10114.1 (1)C10—C11—H11119.7
C8—C9—C10119.9 (1)C11—C12—H12119.6
O4—C10—C11119.1 (1)C7—C12—H12119.7
O4—C10—C9121.4 (1)O3—C13—H13a109.5
C9—C10—C11119.5 (1)O3—C13—H13b109.5
C10—C11—C12120.6 (1)H13a—C13—H13b109.5
C7—C12—C11120.7 (1)O3—C13—H13c109.5
C10—O4—H4109.5H13a—C13—H13c109.5
C2—C1—H1a109.5H13b—C13—H13c109.5
O1—C2—C3—C671.9 (2)C13—O3—C9—C84.7 (2)
C1—C2—C3—C6109.3 (2)C13—O3—C9—C10176.4 (1)
O1—C2—C3—C4106.5 (2)C7—C8—C9—O3179.6 (1)
C1—C2—C3—C472.4 (2)C7—C8—C9—C101.6 (2)
O2—C4—C3—C6178.3 (2)O3—C9—C10—O41.3 (2)
C2—C3—C4—O23.3 (2)C8—C9—C10—O4177.6 (1)
C6—C3—C4—C52.8 (2)O3—C9—C10—C11179.8 (1)
C2—C3—C4—C5175.6 (2)C8—C9—C10—C111.3 (2)
C4—C3—C6—C7176.0 (1)O4—C10—C11—C12178.5 (1)
C2—C3—C6—C75.8 (3)C9—C10—C11—C120.4 (2)
C3—C6—C7—C1216.3 (3)C10—C11—C12—C70.1 (2)
C3—C6—C7—C8165.8 (2)C8—C7—C12—C110.2 (2)
C12—C7—C8—C91.0 (2)C6—C7—C12—C11178.1 (1)
C6—C7—C8—C9179.2 (1)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O4—H4···O2i0.851.982.746 (2)149
Symmetry code: (i) x+1/2, y1/2, z.
 

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