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In the almost planar molecule of the title compound, C13H14O3, the dihedral angle between the benzofuran fused ring system and the acrylate unit is 1.51 (7)°.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807013827/hb2339sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536807013827/hb2339Isup2.hkl
Contains datablock I

CCDC reference: 643018

Key indicators

  • Single-crystal X-ray study
  • T = 294 K
  • Mean [sigma](C-C) = 0.002 Å
  • R factor = 0.043
  • wR factor = 0.108
  • Data-to-parameter ratio = 16.0

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ?
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 1 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 0 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 0 ALERT type 5 Informative message, check

Computing details top

Data collection: SMART (Bruker, 1999); 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: SHELXTL (Bruker, 1997); software used to prepare material for publication: SHELXTL.

(I) top
Crystal data top
C13H14O3F(000) = 464
Mr = 218.24Dx = 1.258 Mg m3
Monoclinic, P21/cMelting point: 329 K
Hall symbol: -P 2ybcMo Kα radiation, λ = 0.71073 Å
a = 7.7498 (12) ÅCell parameters from 2021 reflections
b = 20.334 (4) Åθ = 2.8–24.1°
c = 7.7582 (13) ŵ = 0.09 mm1
β = 109.544 (10)°T = 294 K
V = 1152.1 (4) Å3Block, colorless
Z = 40.30 × 0.28 × 0.26 mm
Data collection top
Bruker Smart 1000 CCD
diffractometer
2353 independent reflections
Radiation source: fine-focus sealed tube1439 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.051
ω scansθmax = 26.4°, θmin = 2.0°
Absorption correction: multi-scan
SADABS (Sheldrick, 1998)
h = 79
Tmin = 0.974, Tmax = 0.977k = 2524
6521 measured reflectionsl = 97
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.043H-atom parameters constrained
wR(F2) = 0.109 w = 1/[σ2(Fo2) + (0.043P)2 + 0.1475P]
where P = (Fo2 + 2Fc2)/3
S = 1.03(Δ/σ)max = 0.001
2353 reflectionsΔρmax = 0.26 e Å3
147 parametersΔρmin = 0.23 e Å3
0 restraintsExtinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.029 (3)
Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O10.58324 (18)0.65676 (6)1.34747 (15)0.0749 (4)
O20.01394 (16)0.65596 (5)0.16230 (15)0.0650 (3)
O30.0525 (2)0.55682 (6)0.26556 (17)0.0934 (5)
C10.5861 (3)0.59447 (9)1.4398 (2)0.0731 (5)
H1A0.54030.60021.54090.088*
H1B0.71030.57771.48780.088*
C20.4644 (2)0.54643 (8)1.2997 (2)0.0639 (5)
H2A0.53120.50701.29030.077*
H2B0.35730.53421.33060.077*
C30.4124 (2)0.58581 (7)1.1260 (2)0.0510 (4)
C40.3101 (2)0.57040 (7)0.9487 (2)0.0532 (4)
H40.26130.52840.92080.064*
C50.2786 (2)0.61746 (7)0.8097 (2)0.0506 (4)
C60.3555 (2)0.68010 (7)0.8572 (2)0.0560 (4)
H60.33610.71190.76640.067*
C70.4588 (2)0.69599 (8)1.0342 (2)0.0599 (4)
H70.50930.73771.06370.072*
C80.4851 (2)0.64823 (8)1.1662 (2)0.0541 (4)
C90.1670 (2)0.59998 (8)0.6225 (2)0.0558 (4)
H90.12010.55750.60650.067*
C100.1240 (2)0.63648 (8)0.4734 (2)0.0613 (5)
H100.16660.67950.48220.074*
C110.0107 (2)0.61108 (8)0.2941 (2)0.0599 (4)
C120.1210 (2)0.63665 (8)0.0220 (2)0.0617 (5)
H12A0.24240.62270.02710.074*
H12B0.06230.60040.06200.074*
C130.1336 (3)0.69518 (9)0.1415 (2)0.0755 (5)
H13A0.19460.73030.10230.113*
H13B0.20160.68390.26590.113*
H13C0.01260.70900.13320.113*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0934 (9)0.0675 (8)0.0565 (8)0.0119 (6)0.0152 (7)0.0086 (6)
O20.0727 (8)0.0591 (7)0.0551 (7)0.0034 (6)0.0106 (6)0.0028 (6)
O30.1228 (12)0.0619 (8)0.0731 (9)0.0288 (8)0.0030 (8)0.0036 (6)
C10.0791 (13)0.0795 (13)0.0593 (11)0.0050 (10)0.0215 (10)0.0033 (9)
C20.0789 (12)0.0564 (10)0.0579 (11)0.0068 (8)0.0248 (9)0.0012 (8)
C30.0544 (9)0.0471 (9)0.0545 (10)0.0039 (7)0.0223 (8)0.0014 (7)
C40.0581 (10)0.0416 (8)0.0600 (10)0.0008 (7)0.0200 (8)0.0022 (8)
C50.0491 (9)0.0463 (9)0.0572 (10)0.0031 (7)0.0190 (8)0.0027 (7)
C60.0617 (10)0.0472 (9)0.0615 (11)0.0015 (7)0.0236 (9)0.0052 (8)
C70.0683 (11)0.0472 (9)0.0652 (11)0.0087 (8)0.0237 (9)0.0071 (8)
C80.0558 (9)0.0541 (9)0.0533 (10)0.0010 (7)0.0195 (8)0.0071 (8)
C90.0568 (10)0.0476 (9)0.0615 (11)0.0020 (7)0.0177 (8)0.0003 (8)
C100.0663 (11)0.0484 (9)0.0629 (11)0.0023 (8)0.0131 (9)0.0005 (8)
C110.0605 (11)0.0536 (10)0.0620 (11)0.0010 (8)0.0156 (9)0.0031 (8)
C120.0564 (10)0.0692 (11)0.0553 (10)0.0018 (8)0.0134 (8)0.0054 (8)
C130.0785 (13)0.0783 (12)0.0632 (12)0.0070 (10)0.0151 (10)0.0061 (10)
Geometric parameters (Å, º) top
O1—C81.3675 (19)C5—C91.463 (2)
O1—C11.452 (2)C6—C71.377 (2)
O2—C111.3358 (19)C6—H60.9300
O2—C121.4470 (19)C7—C81.376 (2)
O3—C111.1976 (19)C7—H70.9300
C1—C21.530 (2)C9—C101.320 (2)
C1—H1A0.9700C9—H90.9300
C1—H1B0.9700C10—C111.468 (2)
C2—C31.502 (2)C10—H100.9300
C2—H2A0.9700C12—C131.492 (2)
C2—H2B0.9700C12—H12A0.9700
C3—C41.374 (2)C12—H12B0.9700
C3—C81.382 (2)C13—H13A0.9600
C4—C51.401 (2)C13—H13B0.9600
C4—H40.9300C13—H13C0.9600
C5—C61.402 (2)
C8—O1—C1107.96 (12)C8—C7—H7121.0
C11—O2—C12117.33 (13)C6—C7—H7121.0
O1—C1—C2107.60 (13)O1—C8—C7124.66 (14)
O1—C1—H1A110.2O1—C8—C3113.17 (14)
C2—C1—H1A110.2C7—C8—C3122.17 (15)
O1—C1—H1B110.2C10—C9—C5128.69 (15)
C2—C1—H1B110.2C10—C9—H9115.7
H1A—C1—H1B108.5C5—C9—H9115.7
C3—C2—C1102.35 (13)C9—C10—C11121.89 (16)
C3—C2—H2A111.3C9—C10—H10119.1
C1—C2—H2A111.3C11—C10—H10119.1
C3—C2—H2B111.3O3—C11—O2122.88 (16)
C1—C2—H2B111.3O3—C11—C10125.27 (16)
H2A—C2—H2B109.2O2—C11—C10111.84 (15)
C4—C3—C8119.39 (14)O2—C12—C13107.11 (14)
C4—C3—C2131.93 (14)O2—C12—H12A110.3
C8—C3—C2108.67 (14)C13—C12—H12A110.3
C3—C4—C5120.56 (14)O2—C12—H12B110.3
C3—C4—H4119.7C13—C12—H12B110.3
C5—C4—H4119.7H12A—C12—H12B108.5
C4—C5—C6117.96 (14)C12—C13—H13A109.5
C4—C5—C9119.40 (14)C12—C13—H13B109.5
C6—C5—C9122.64 (14)H13A—C13—H13B109.5
C7—C6—C5121.96 (15)C12—C13—H13C109.5
C7—C6—H6119.0H13A—C13—H13C109.5
C5—C6—H6119.0H13B—C13—H13C109.5
C8—C7—C6117.95 (14)
C8—O1—C1—C24.81 (18)C6—C7—C8—C30.3 (2)
O1—C1—C2—C34.88 (18)C4—C3—C8—O1179.87 (13)
C1—C2—C3—C4177.45 (16)C2—C3—C8—O10.56 (19)
C1—C2—C3—C83.36 (18)C4—C3—C8—C70.0 (2)
C8—C3—C4—C50.4 (2)C2—C3—C8—C7179.32 (15)
C2—C3—C4—C5178.76 (16)C4—C5—C9—C10178.91 (16)
C3—C4—C5—C60.4 (2)C6—C5—C9—C101.5 (3)
C3—C4—C5—C9179.15 (14)C5—C9—C10—C11179.50 (15)
C4—C5—C6—C70.2 (2)C12—O2—C11—O30.5 (3)
C9—C5—C6—C7179.40 (14)C12—O2—C11—C10179.01 (13)
C5—C6—C7—C80.2 (2)C9—C10—C11—O30.3 (3)
C1—O1—C8—C7177.39 (16)C9—C10—C11—O2179.26 (15)
C1—O1—C8—C32.74 (19)C11—O2—C12—C13178.25 (14)
C6—C7—C8—O1179.59 (15)
 

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