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The mol­ecule of the title compound, C11H12O3, is essentially planar, the maximum deviation from the least-squares plane through all non-H atoms being 0.37 (1) Å for the methyl group. The mol­ecular packing is made up of a network of C—H...O hydrogen-bonding inter­actions involving the carbonyl groups.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807013876/su2006sup1.cif
Contains datablocks global, II

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536807013876/su2006IIsup2.hkl
Contains datablock II

CCDC reference: 647347

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.002 Å
  • R factor = 0.036
  • wR factor = 0.111
  • Data-to-parameter ratio = 9.5

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low ....... 0.98 PLAT230_ALERT_2_C Hirshfeld Test Diff for O1 - C4 .. 5.51 su PLAT230_ALERT_2_C Hirshfeld Test Diff for C5 - C6 .. 5.04 su PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C10 PLAT380_ALERT_4_C Check Incorrectly? Oriented X(sp2)-Methyl Moiety C11 PLAT480_ALERT_4_C Long H...A H-Bond Reported H5 .. O3 .. 2.85 Ang. PLAT480_ALERT_4_C Long H...A H-Bond Reported H9B .. O3 .. 2.64 Ang. PLAT480_ALERT_4_C Long H...A H-Bond Reported H11B .. O3 .. 2.62 Ang.
Alert level G REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is correct. If it is not, please give the correct count in the _publ_section_exptl_refinement section of the submitted CIF. From the CIF: _diffrn_reflns_theta_max 74.87 From the CIF: _reflns_number_total 1207 Count of symmetry unique reflns 1236 Completeness (_total/calc) 97.65% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 0 Fraction of Friedel pairs measured 0.000 Are heavy atom types Z>Si present no PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature 293 K PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature . 293 K
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 8 ALERT level C = Check and explain 3 ALERT level G = General alerts; check 2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 3 ALERT type 2 Indicator that the structure model may be wrong or deficient 1 ALERT type 3 Indicator that the structure quality may be low 5 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Computing details top

Data collection: CrysAlis CCD (Oxford Diffraction, 2006); cell refinement: CrysAlis RED (Oxford Diffraction, 2006); data reduction: CrysAlis RED; program(s) used to solve structure: SIR2004 (Burla et al., 2005); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX publication routines (Farrugia, 1999).

E-7-(2-furyl)heptan-6-ene-2,5-dione top
Crystal data top
C11H12O3F(000) = 408
Mr = 192.21Dx = 1.247 Mg m3
Orthorhombic, P212121Cu Kα radiation, λ = 1.54184 Å
Hall symbol: P 2ac 2abCell parameters from 2484 reflections
a = 7.8751 (5) Åθ = 4.8–74.5°
b = 9.1651 (3) ŵ = 0.75 mm1
c = 14.1891 (6) ÅT = 293 K
V = 1024.11 (9) Å3Prismatic, colorless
Z = 40.26 × 0.18 × 0.09 mm
Data collection top
Oxford Diffraction Model? CCD
diffractometer
1207 independent reflections
Radiation source: Enhance (Cu) X-ray Source943 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.024
Detector resolution: 8.2640 pixels mm-1θmax = 74.9°, θmin = 5.8°
ω scansh = 69
Absorption correction: multi-scan
(Scale3 Abspack; Oxford Diffraction, 2006)
k = 1110
Tmin = 0.852, Tmax = 0.931l = 1714
4806 measured reflections
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)] = 0.036Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.111H-atom parameters constrained
S = 1.10 w = 1/[σ2(Fo2) + (0.0679P)2 + 0.2503P]
where P = (Fo2 + 2Fc2)/3
1207 reflections(Δ/σ)max < 0.001
127 parametersΔρmax = 0.11 e Å3
0 restraintsΔρmin = 0.12 e Å3
Special details top

Experimental. Scale3 Abspack program including interframe scaling, empirical absorption correction (Blessing) and detector sensitivity correction. (Oxford Diffraction, 2006)

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

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
O10.96353 (15)0.66124 (10)0.31185 (7)0.0785 (4)
O20.82413 (16)0.87193 (10)0.00923 (7)0.0896 (5)
O30.9948 (2)0.45202 (12)0.20236 (8)0.1027 (5)
C10.9713 (3)0.66784 (16)0.40765 (10)0.0856 (6)
C20.8979 (3)0.78917 (16)0.43943 (11)0.0862 (6)
C30.8400 (2)0.86507 (15)0.35994 (10)0.0748 (5)
C40.88060 (18)0.78571 (13)0.28350 (9)0.0643 (4)
C50.85609 (18)0.80832 (13)0.18496 (10)0.0638 (4)
C60.89982 (19)0.71786 (12)0.11535 (9)0.0646 (4)
C70.86828 (19)0.75098 (12)0.01615 (9)0.0643 (4)
C80.8968 (2)0.63014 (13)0.05299 (9)0.0700 (5)
C90.8603 (2)0.66923 (14)0.15378 (9)0.0721 (5)
C100.91406 (19)0.55955 (14)0.22480 (10)0.0681 (5)
C110.8729 (3)0.59242 (17)0.32512 (11)0.0882 (6)
H11.021100.597200.445700.1030*
H20.887100.817800.502000.1030*
H30.783700.954300.360000.0900*
H50.804200.895300.167400.0770*
H60.952500.630200.130600.0780*
H8A0.825700.548100.035400.0840*
H8B1.014100.598600.048300.0840*
H9A0.739100.685000.160400.0870*
H9B0.916400.760900.167900.0870*
H11A0.914000.515000.364500.1320*
H11B0.926000.682500.343100.1320*
H11C0.752100.601000.332300.1320*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.1062 (8)0.0652 (5)0.0640 (6)0.0122 (5)0.0016 (5)0.0002 (4)
O20.1391 (11)0.0618 (6)0.0680 (6)0.0188 (5)0.0066 (6)0.0008 (5)
O30.1468 (11)0.0765 (6)0.0848 (8)0.0310 (7)0.0022 (8)0.0090 (5)
C10.1196 (14)0.0774 (8)0.0599 (9)0.0012 (9)0.0021 (9)0.0081 (7)
C20.1191 (14)0.0808 (8)0.0586 (8)0.0123 (10)0.0077 (9)0.0048 (7)
C30.0908 (11)0.0623 (7)0.0714 (8)0.0041 (7)0.0090 (8)0.0059 (7)
C40.0738 (9)0.0548 (6)0.0643 (8)0.0014 (6)0.0020 (7)0.0010 (5)
C50.0677 (9)0.0574 (6)0.0664 (7)0.0003 (6)0.0010 (7)0.0033 (6)
C60.0747 (9)0.0567 (5)0.0624 (8)0.0034 (6)0.0007 (6)0.0014 (6)
C70.0724 (9)0.0562 (6)0.0642 (8)0.0033 (6)0.0009 (7)0.0032 (5)
C80.0846 (10)0.0603 (6)0.0650 (8)0.0026 (7)0.0002 (7)0.0001 (6)
C90.0853 (10)0.0688 (7)0.0623 (8)0.0066 (6)0.0036 (8)0.0025 (6)
C100.0751 (9)0.0597 (7)0.0696 (8)0.0092 (6)0.0011 (7)0.0033 (6)
C110.1115 (13)0.0874 (9)0.0657 (9)0.0054 (9)0.0059 (10)0.0088 (7)
Geometric parameters (Å, º) top
O1—C11.3620 (17)C10—C111.491 (2)
O1—C41.3747 (16)C1—H10.9300
O2—C71.2163 (15)C2—H20.9300
O3—C101.2153 (18)C3—H30.9300
C1—C21.332 (2)C5—H50.9300
C2—C31.401 (2)C6—H60.9300
C3—C41.3445 (19)C8—H8A0.9700
C4—C51.4266 (19)C8—H8B0.9700
C5—C61.3347 (18)C9—H9A0.9700
C6—C71.4612 (18)C9—H9B0.9700
C7—C81.4965 (17)C11—H11A0.9600
C8—C91.5021 (18)C11—H11B0.9600
C9—C101.4850 (19)C11—H11C0.9600
O2···C3i3.3056 (18)H3···O2vi2.5900
O1···H62.5900H5···O22.5200
O2···H9A2.8300H5···O3ii2.8500
O2···H9B2.5800H6···O12.5900
O2···H52.5200H6···C3vii2.9300
O2···H3i2.5900H8A···O32.8600
O2···H8Bii2.5900H8B···O32.5700
O2···H1iii2.5600H8B···O2iv2.5900
O3···H8A2.8600H9A···O22.8300
O3···H8B2.5700H9A···H11C2.5600
O3···H5iv2.8500H9A···C5ii3.0400
O3···H9Bv2.6400H9A···C6ii2.8900
O3···H11Bv2.6300H9B···O22.5800
C3···O2vi3.3056 (18)H9B···H11B2.5900
C3···H6iii2.9300H9B···O3ix2.6400
C5···H9Aiv3.0400H11B···H2x2.5400
C6···H9Aiv2.8900H11B···H9B2.5900
H1···O2vii2.5600H11B···O3ix2.6300
H2···H11Bviii2.5400H11C···H9A2.5600
C1—O1—C4106.05 (11)C4—C3—H3126.00
O1—C1—C2110.82 (14)C4—C5—H5117.00
C1—C2—C3106.45 (14)C6—C5—H5117.00
C2—C3—C4107.66 (13)C5—C6—H6119.00
O1—C4—C3109.02 (11)C7—C6—H6119.00
O1—C4—C5118.14 (11)C7—C8—H8A109.00
C3—C4—C5132.84 (12)C7—C8—H8B109.00
C4—C5—C6126.88 (12)C9—C8—H8A109.00
C5—C6—C7122.68 (11)C9—C8—H8B109.00
O2—C7—C6121.54 (11)H8A—C8—H8B108.00
O2—C7—C8121.55 (12)C8—C9—H9A108.00
C6—C7—C8116.89 (10)C8—C9—H9B108.00
C7—C8—C9114.77 (11)C10—C9—H9A108.00
C8—C9—C10115.47 (11)C10—C9—H9B108.00
O3—C10—C9121.35 (13)H9A—C9—H9B107.00
O3—C10—C11121.86 (13)C10—C11—H11A109.00
C9—C10—C11116.69 (12)C10—C11—H11B109.00
O1—C1—H1125.00C10—C11—H11C109.00
C2—C1—H1125.00H11A—C11—H11B110.00
C1—C2—H2127.00H11A—C11—H11C109.00
C3—C2—H2127.00H11B—C11—H11C109.00
C2—C3—H3126.00
C4—O1—C1—C20.0 (2)C4—C5—C6—C7179.70 (14)
C1—O1—C4—C30.14 (18)C5—C6—C7—O211.4 (2)
C1—O1—C4—C5179.30 (14)C5—C6—C7—C8170.02 (14)
O1—C1—C2—C30.1 (2)O2—C7—C8—C92.2 (2)
C1—C2—C3—C40.2 (2)C6—C7—C8—C9179.20 (13)
C2—C3—C4—O10.22 (18)C7—C8—C9—C10170.48 (13)
C2—C3—C4—C5179.21 (17)C8—C9—C10—O36.0 (2)
O1—C4—C5—C62.7 (2)C8—C9—C10—C11177.48 (15)
C3—C4—C5—C6178.35 (16)
Symmetry codes: (i) x+3/2, y+2, z1/2; (ii) x1/2, y+3/2, z; (iii) x+2, y+1/2, z+1/2; (iv) x+1/2, y+3/2, z; (v) x+2, y1/2, z1/2; (vi) x+3/2, y+2, z+1/2; (vii) x+2, y1/2, z+1/2; (viii) x, y, z+1; (ix) x+2, y+1/2, z1/2; (x) x, y, z1.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C1—H1···O2vii0.932.563.468 (2)165
C3—H3···O2vi0.932.593.3056 (18)134
C5—H5···O20.932.522.8276 (17)100
C8—H8B···O2iv0.972.593.479 (2)153
C5—H5···O3ii0.932.853.603 (2)139
C9—H9B···O3ix0.972.643.491 (2)147
C11—H11B···O3ix0.962.623.478 (2)148
Symmetry codes: (ii) x1/2, y+3/2, z; (iv) x+1/2, y+3/2, z; (vi) x+3/2, y+2, z+1/2; (vii) x+2, y1/2, z+1/2; (ix) x+2, y+1/2, z1/2.
 

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