The molecule of the title compound, C
11H
12O
3, 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
CCDC reference: 647347
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (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
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
C11H12O3 | F(000) = 408 |
Mr = 192.21 | Dx = 1.247 Mg m−3 |
Orthorhombic, P212121 | Cu Kα radiation, λ = 1.54184 Å |
Hall symbol: P 2ac 2ab | Cell parameters from 2484 reflections |
a = 7.8751 (5) Å | θ = 4.8–74.5° |
b = 9.1651 (3) Å | µ = 0.75 mm−1 |
c = 14.1891 (6) Å | T = 293 K |
V = 1024.11 (9) Å3 | Prismatic, colorless |
Z = 4 | 0.26 × 0.18 × 0.09 mm |
Data collection top
Oxford Diffraction Model? CCD diffractometer | 1207 independent reflections |
Radiation source: Enhance (Cu) X-ray Source | 943 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.024 |
Detector resolution: 8.2640 pixels mm-1 | θmax = 74.9°, θmin = 5.8° |
ω scans | h = −6→9 |
Absorption correction: multi-scan (Scale3 Abspack; Oxford Diffraction, 2006) | k = −11→10 |
Tmin = 0.852, Tmax = 0.931 | l = −17→14 |
4806 measured reflections | |
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)] = 0.036 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.111 | H-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 parameters | Δρmax = 0.11 e Å−3 |
0 restraints | Δρmin = −0.12 e Å−3 |
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 | x | y | z | Uiso*/Ueq | |
O1 | 0.96353 (15) | 0.66124 (10) | 0.31185 (7) | 0.0785 (4) | |
O2 | 0.82413 (16) | 0.87193 (10) | −0.00923 (7) | 0.0896 (5) | |
O3 | 0.9948 (2) | 0.45202 (12) | −0.20236 (8) | 0.1027 (5) | |
C1 | 0.9713 (3) | 0.66784 (16) | 0.40765 (10) | 0.0856 (6) | |
C2 | 0.8979 (3) | 0.78917 (16) | 0.43943 (11) | 0.0862 (6) | |
C3 | 0.8400 (2) | 0.86507 (15) | 0.35994 (10) | 0.0748 (5) | |
C4 | 0.88060 (18) | 0.78571 (13) | 0.28350 (9) | 0.0643 (4) | |
C5 | 0.85609 (18) | 0.80832 (13) | 0.18496 (10) | 0.0638 (4) | |
C6 | 0.89982 (19) | 0.71786 (12) | 0.11535 (9) | 0.0646 (4) | |
C7 | 0.86828 (19) | 0.75098 (12) | 0.01615 (9) | 0.0643 (4) | |
C8 | 0.8968 (2) | 0.63014 (13) | −0.05299 (9) | 0.0700 (5) | |
C9 | 0.8603 (2) | 0.66923 (14) | −0.15378 (9) | 0.0721 (5) | |
C10 | 0.91406 (19) | 0.55955 (14) | −0.22480 (10) | 0.0681 (5) | |
C11 | 0.8729 (3) | 0.59242 (17) | −0.32512 (11) | 0.0882 (6) | |
H1 | 1.02110 | 0.59720 | 0.44570 | 0.1030* | |
H2 | 0.88710 | 0.81780 | 0.50200 | 0.1030* | |
H3 | 0.78370 | 0.95430 | 0.36000 | 0.0900* | |
H5 | 0.80420 | 0.89530 | 0.16740 | 0.0770* | |
H6 | 0.95250 | 0.63020 | 0.13060 | 0.0780* | |
H8A | 0.82570 | 0.54810 | −0.03540 | 0.0840* | |
H8B | 1.01410 | 0.59860 | −0.04830 | 0.0840* | |
H9A | 0.73910 | 0.68500 | −0.16040 | 0.0870* | |
H9B | 0.91640 | 0.76090 | −0.16790 | 0.0870* | |
H11A | 0.91400 | 0.51500 | −0.36450 | 0.1320* | |
H11B | 0.92600 | 0.68250 | −0.34310 | 0.1320* | |
H11C | 0.75210 | 0.60100 | −0.33230 | 0.1320* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1 | 0.1062 (8) | 0.0652 (5) | 0.0640 (6) | 0.0122 (5) | −0.0016 (5) | −0.0002 (4) |
O2 | 0.1391 (11) | 0.0618 (6) | 0.0680 (6) | 0.0188 (5) | −0.0066 (6) | 0.0008 (5) |
O3 | 0.1468 (11) | 0.0765 (6) | 0.0848 (8) | 0.0310 (7) | −0.0022 (8) | −0.0090 (5) |
C1 | 0.1196 (14) | 0.0774 (8) | 0.0599 (9) | −0.0012 (9) | −0.0021 (9) | 0.0081 (7) |
C2 | 0.1191 (14) | 0.0808 (8) | 0.0586 (8) | −0.0123 (10) | 0.0077 (9) | −0.0048 (7) |
C3 | 0.0908 (11) | 0.0623 (7) | 0.0714 (8) | −0.0041 (7) | 0.0090 (8) | −0.0059 (7) |
C4 | 0.0738 (9) | 0.0548 (6) | 0.0643 (8) | 0.0014 (6) | 0.0020 (7) | 0.0010 (5) |
C5 | 0.0677 (9) | 0.0574 (6) | 0.0664 (7) | −0.0003 (6) | −0.0010 (7) | 0.0033 (6) |
C6 | 0.0747 (9) | 0.0567 (5) | 0.0624 (8) | 0.0034 (6) | −0.0007 (6) | 0.0014 (6) |
C7 | 0.0724 (9) | 0.0562 (6) | 0.0642 (8) | 0.0033 (6) | 0.0009 (7) | 0.0032 (5) |
C8 | 0.0846 (10) | 0.0603 (6) | 0.0650 (8) | 0.0026 (7) | 0.0002 (7) | 0.0001 (6) |
C9 | 0.0853 (10) | 0.0688 (7) | 0.0623 (8) | 0.0066 (6) | −0.0036 (8) | −0.0025 (6) |
C10 | 0.0751 (9) | 0.0597 (7) | 0.0696 (8) | −0.0092 (6) | −0.0011 (7) | −0.0033 (6) |
C11 | 0.1115 (13) | 0.0874 (9) | 0.0657 (9) | −0.0054 (9) | −0.0059 (10) | −0.0088 (7) |
Geometric parameters (Å, º) top
O1—C1 | 1.3620 (17) | C10—C11 | 1.491 (2) |
O1—C4 | 1.3747 (16) | C1—H1 | 0.9300 |
O2—C7 | 1.2163 (15) | C2—H2 | 0.9300 |
O3—C10 | 1.2153 (18) | C3—H3 | 0.9300 |
C1—C2 | 1.332 (2) | C5—H5 | 0.9300 |
C2—C3 | 1.401 (2) | C6—H6 | 0.9300 |
C3—C4 | 1.3445 (19) | C8—H8A | 0.9700 |
C4—C5 | 1.4266 (19) | C8—H8B | 0.9700 |
C5—C6 | 1.3347 (18) | C9—H9A | 0.9700 |
C6—C7 | 1.4612 (18) | C9—H9B | 0.9700 |
C7—C8 | 1.4965 (17) | C11—H11A | 0.9600 |
C8—C9 | 1.5021 (18) | C11—H11B | 0.9600 |
C9—C10 | 1.4850 (19) | C11—H11C | 0.9600 |
| | | |
O2···C3i | 3.3056 (18) | H3···O2vi | 2.5900 |
O1···H6 | 2.5900 | H5···O2 | 2.5200 |
O2···H9A | 2.8300 | H5···O3ii | 2.8500 |
O2···H9B | 2.5800 | H6···O1 | 2.5900 |
O2···H5 | 2.5200 | H6···C3vii | 2.9300 |
O2···H3i | 2.5900 | H8A···O3 | 2.8600 |
O2···H8Bii | 2.5900 | H8B···O3 | 2.5700 |
O2···H1iii | 2.5600 | H8B···O2iv | 2.5900 |
O3···H8A | 2.8600 | H9A···O2 | 2.8300 |
O3···H8B | 2.5700 | H9A···H11C | 2.5600 |
O3···H5iv | 2.8500 | H9A···C5ii | 3.0400 |
O3···H9Bv | 2.6400 | H9A···C6ii | 2.8900 |
O3···H11Bv | 2.6300 | H9B···O2 | 2.5800 |
C3···O2vi | 3.3056 (18) | H9B···H11B | 2.5900 |
C3···H6iii | 2.9300 | H9B···O3ix | 2.6400 |
C5···H9Aiv | 3.0400 | H11B···H2x | 2.5400 |
C6···H9Aiv | 2.8900 | H11B···H9B | 2.5900 |
H1···O2vii | 2.5600 | H11B···O3ix | 2.6300 |
H2···H11Bviii | 2.5400 | H11C···H9A | 2.5600 |
| | | |
C1—O1—C4 | 106.05 (11) | C4—C3—H3 | 126.00 |
O1—C1—C2 | 110.82 (14) | C4—C5—H5 | 117.00 |
C1—C2—C3 | 106.45 (14) | C6—C5—H5 | 117.00 |
C2—C3—C4 | 107.66 (13) | C5—C6—H6 | 119.00 |
O1—C4—C3 | 109.02 (11) | C7—C6—H6 | 119.00 |
O1—C4—C5 | 118.14 (11) | C7—C8—H8A | 109.00 |
C3—C4—C5 | 132.84 (12) | C7—C8—H8B | 109.00 |
C4—C5—C6 | 126.88 (12) | C9—C8—H8A | 109.00 |
C5—C6—C7 | 122.68 (11) | C9—C8—H8B | 109.00 |
O2—C7—C6 | 121.54 (11) | H8A—C8—H8B | 108.00 |
O2—C7—C8 | 121.55 (12) | C8—C9—H9A | 108.00 |
C6—C7—C8 | 116.89 (10) | C8—C9—H9B | 108.00 |
C7—C8—C9 | 114.77 (11) | C10—C9—H9A | 108.00 |
C8—C9—C10 | 115.47 (11) | C10—C9—H9B | 108.00 |
O3—C10—C9 | 121.35 (13) | H9A—C9—H9B | 107.00 |
O3—C10—C11 | 121.86 (13) | C10—C11—H11A | 109.00 |
C9—C10—C11 | 116.69 (12) | C10—C11—H11B | 109.00 |
O1—C1—H1 | 125.00 | C10—C11—H11C | 109.00 |
C2—C1—H1 | 125.00 | H11A—C11—H11B | 110.00 |
C1—C2—H2 | 127.00 | H11A—C11—H11C | 109.00 |
C3—C2—H2 | 127.00 | H11B—C11—H11C | 109.00 |
C2—C3—H3 | 126.00 | | |
| | | |
C4—O1—C1—C2 | 0.0 (2) | C4—C5—C6—C7 | 179.70 (14) |
C1—O1—C4—C3 | 0.14 (18) | C5—C6—C7—O2 | 11.4 (2) |
C1—O1—C4—C5 | 179.30 (14) | C5—C6—C7—C8 | −170.02 (14) |
O1—C1—C2—C3 | −0.1 (2) | O2—C7—C8—C9 | −2.2 (2) |
C1—C2—C3—C4 | 0.2 (2) | C6—C7—C8—C9 | 179.20 (13) |
C2—C3—C4—O1 | −0.22 (18) | C7—C8—C9—C10 | 170.48 (13) |
C2—C3—C4—C5 | −179.21 (17) | C8—C9—C10—O3 | −6.0 (2) |
O1—C4—C5—C6 | 2.7 (2) | C8—C9—C10—C11 | 177.48 (15) |
C3—C4—C5—C6 | −178.35 (16) | | |
Symmetry codes: (i) −x+3/2, −y+2, z−1/2; (ii) x−1/2, −y+3/2, −z; (iii) −x+2, y+1/2, −z+1/2; (iv) x+1/2, −y+3/2, −z; (v) −x+2, y−1/2, −z−1/2; (vi) −x+3/2, −y+2, z+1/2; (vii) −x+2, y−1/2, −z+1/2; (viii) x, y, z+1; (ix) −x+2, y+1/2, −z−1/2; (x) x, y, z−1. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C1—H1···O2vii | 0.93 | 2.56 | 3.468 (2) | 165 |
C3—H3···O2vi | 0.93 | 2.59 | 3.3056 (18) | 134 |
C5—H5···O2 | 0.93 | 2.52 | 2.8276 (17) | 100 |
C8—H8B···O2iv | 0.97 | 2.59 | 3.479 (2) | 153 |
C5—H5···O3ii | 0.93 | 2.85 | 3.603 (2) | 139 |
C9—H9B···O3ix | 0.97 | 2.64 | 3.491 (2) | 147 |
C11—H11B···O3ix | 0.96 | 2.62 | 3.478 (2) | 148 |
Symmetry codes: (ii) x−1/2, −y+3/2, −z; (iv) x+1/2, −y+3/2, −z; (vi) −x+3/2, −y+2, z+1/2; (vii) −x+2, y−1/2, −z+1/2; (ix) −x+2, y+1/2, −z−1/2. |