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In the title compound, C17H16O5, the dihydrofuran ring adopts an envelope conformation while the methyl­enedioxy­phenyl ring system is essentially planar. The vinyl group is inclined to the dihydrofuran ring by 31.06 (18)o. The dihedral angle between the atoms defining the planar part of the dihydrofuran ring and the aryl ring is 24.86 (7)o.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807023732/pv2014sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536807023732/pv2014Isup2.hkl
Contains datablock I

CCDC reference: 651530

Key indicators

  • Single-crystal X-ray study
  • T = 296 K
  • Mean [sigma](C-C) = 0.004 Å
  • R factor = 0.056
  • wR factor = 0.203
  • Data-to-parameter ratio = 18.4

checkCIF/PLATON results

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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

Comment top

Organic photochromic compounds, such as fulgides are potential candidates for application in erasable optical information media, attempts have been made to improve their photochromic properties (Uchida et al., 1995; Asiri, 2003). In order to achieve certain desirable properties such as absorption at longer wavelengths and thus higher fatigue resistance to coloration-bleaching cycles, improvements have been made by modifying the fulgide frame (Heller et al., 2000). We report here the crystal structure of the title compound, (I).

Related literature top

For related literature, see: Asiri (2003); Heller et al. (2000); Uchida et al. (1995).

Experimental top

The 2-(benzo[d][1,3]dioxol-5-ylmethylene)-3-(pentan-2-ylidene)succinic acid (0.01 mmol) was dissolved in dichloromethane (10 ml), and to this mixture was added acetyl chloride (5 ml) dropwise with stirring at 273 K, and the mixture was stirred at room temperature for 5 h. After removal of the excess acetyl chloride and dichloromethane, the residue was purified using flash column chromatography on silica gel (petroleum ether/ethyl acetate = 2/1; v/v) and recrystallized with ethyl acetate to give a solid (yield 4%) as minor product. Crystals of (I) suitable for X-ray diffraction were obtained by slow evaporation of a solution of the solid in ethyl acetate at room temperature for 15 days.

Refinement top

H atoms were positioned geometrically (C - H = 0.93 - 0.97 Å) and refined as riding, with Uiso(H) = 1.2Ueq(C).

Structure description top

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# Following replaced by publCIF - tuesday May 8 16:03:35 2007

The stucture of the title compound, (I), is shown below. Dimensions are available in the archived CIF.

For related literature, see [type here to add references to related literature].

Computing details top

Data collection: APEX2 Software Suite (Bruker, 2005); cell refinement: APEX2 Software Suite; data reduction: APEX2 Software Suite; program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

Figures top
[Figure 1] Fig. 1. The molecular structure of (I), showing the atom-numbering scheme with 50% probability displacement ellipsoids; H atoms have been omitted for clarity.
(3E,4Z)-3-[1,3-Benzodioxol-5-yl)methylene]-4-(2-πentylidene)tetrahydrofuran-2,5-dione top
Crystal data top
C17H16O5F(000) = 632
Mr = 300.30Dx = 1.337 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 4386 reflections
a = 7.8597 (11) Åθ = 2.7–23.6°
b = 15.383 (3) ŵ = 0.10 mm1
c = 12.781 (2) ÅT = 296 K
β = 105.117 (10)°Plate, yellow
V = 1491.8 (4) Å30.30 × 0.25 × 0.15 mm
Z = 4
Data collection top
Bruker APEX2 CCD area-detector
diffractometer
3695 independent reflections
Radiation source: fine-focus sealed tube2084 reflections with I > 2.0σ(I)
Graphite monochromatorRint = 0.024
φ and ω scansθmax = 28.4°, θmin = 2.1°
Absorption correction: multi-scan
(APEX2 Software Suite; Bruker, 2005)
h = 1010
Tmin = 0.971, Tmax = 0.985k = 1320
14935 measured reflectionsl = 1716
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)] = 0.056Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.203H-atom parameters constrained
S = 0.94 w = 1/[σ2(Fo2) + (0.1P)2 + 0.6902P]
where P = (Fo2 + 2Fc2)/3
3695 reflections(Δ/σ)max < 0.001
201 parametersΔρmax = 0.40 e Å3
0 restraintsΔρmin = 0.16 e Å3
Crystal data top
C17H16O5V = 1491.8 (4) Å3
Mr = 300.30Z = 4
Monoclinic, P21/cMo Kα radiation
a = 7.8597 (11) ŵ = 0.10 mm1
b = 15.383 (3) ÅT = 296 K
c = 12.781 (2) Å0.30 × 0.25 × 0.15 mm
β = 105.117 (10)°
Data collection top
Bruker APEX2 CCD area-detector
diffractometer
3695 independent reflections
Absorption correction: multi-scan
(APEX2 Software Suite; Bruker, 2005)
2084 reflections with I > 2.0σ(I)
Tmin = 0.971, Tmax = 0.985Rint = 0.024
14935 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0560 restraints
wR(F2) = 0.203H-atom parameters constrained
S = 0.94Δρmax = 0.40 e Å3
3695 reflectionsΔρmin = 0.16 e Å3
201 parameters
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
O10.1718 (3)0.82579 (16)1.02559 (15)0.0841 (6)
O20.3854 (2)0.80813 (15)0.86514 (16)0.0836 (6)
O30.5532 (3)1.07745 (17)0.87030 (18)0.0974 (7)
O40.4746 (2)1.07754 (12)0.68911 (16)0.0727 (5)
O50.3415 (3)1.05288 (15)0.51414 (17)0.0840 (6)
C70.0484 (3)0.89375 (17)0.94481 (19)0.0605 (6)
H20.13340.90091.01010.073*
C130.2597 (3)0.87611 (18)0.6060 (2)0.0622 (6)
C120.2982 (3)0.95405 (16)0.65540 (19)0.0572 (6)
C50.0529 (3)0.90996 (17)0.75049 (19)0.0608 (6)
H80.03180.92800.68560.073*
C60.0795 (3)0.91969 (16)0.84621 (19)0.0569 (6)
C20.1117 (3)0.85766 (16)0.94102 (19)0.0587 (6)
C30.2401 (3)0.84713 (16)0.8457 (2)0.0592 (6)
C110.3643 (3)1.02957 (18)0.6057 (2)0.0655 (7)
C40.2156 (3)0.87400 (19)0.7491 (2)0.0661 (7)
H140.30410.86850.68500.079*
C160.0476 (3)0.87491 (19)0.4242 (2)0.0713 (7)
H15A0.02830.83850.45470.086*
H15B0.01430.93500.43090.086*
C90.3288 (3)0.97795 (17)0.7705 (2)0.0614 (6)
C150.2383 (3)0.8619 (2)0.4888 (2)0.0719 (7)
H17A0.27520.80330.47730.086*
H17B0.31330.90210.46300.086*
C80.2473 (3)0.96253 (17)0.8495 (2)0.0619 (6)
H180.30800.98250.91760.074*
C100.4634 (3)1.04727 (19)0.7889 (2)0.0678 (7)
C140.2331 (4)0.79731 (18)0.6670 (2)0.0775 (8)
H20A0.26870.80930.74340.116*
H20B0.30260.75040.65070.116*
H20C0.11080.78130.64640.116*
C10.3455 (4)0.7941 (2)0.9778 (3)0.0824 (8)
H21A0.35190.73260.99280.099*
H21B0.42980.82451.00810.099*
C170.0189 (6)0.8531 (2)0.3058 (2)0.1014 (11)
H22A0.09410.88870.27530.152*
H22B0.10200.86370.26820.152*
H22C0.04620.79290.29850.152*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0716 (11)0.1183 (17)0.0632 (11)0.0185 (11)0.0189 (9)0.0098 (11)
O20.0510 (9)0.1139 (17)0.0833 (13)0.0151 (10)0.0127 (8)0.0099 (11)
O30.0794 (13)0.1191 (19)0.0881 (14)0.0453 (13)0.0117 (11)0.0243 (13)
O40.0639 (10)0.0713 (12)0.0861 (13)0.0182 (9)0.0252 (9)0.0034 (10)
O50.0748 (12)0.1033 (16)0.0788 (13)0.0082 (11)0.0288 (10)0.0186 (11)
C70.0569 (12)0.0686 (16)0.0497 (12)0.0075 (11)0.0028 (10)0.0000 (11)
C130.0421 (10)0.0699 (17)0.0715 (15)0.0003 (10)0.0090 (10)0.0049 (12)
C120.0437 (10)0.0632 (15)0.0637 (14)0.0021 (10)0.0120 (9)0.0017 (11)
C50.0562 (12)0.0693 (16)0.0525 (13)0.0033 (11)0.0067 (10)0.0061 (11)
C60.0544 (12)0.0571 (14)0.0549 (13)0.0060 (10)0.0065 (10)0.0023 (10)
C20.0573 (12)0.0636 (15)0.0547 (13)0.0010 (11)0.0137 (10)0.0038 (11)
C30.0455 (11)0.0631 (15)0.0667 (14)0.0002 (10)0.0102 (10)0.0014 (11)
C110.0480 (11)0.0743 (18)0.0766 (17)0.0036 (11)0.0207 (11)0.0002 (14)
C40.0494 (11)0.0827 (19)0.0587 (14)0.0002 (12)0.0009 (10)0.0032 (12)
C160.0633 (14)0.0708 (18)0.0796 (18)0.0047 (12)0.0182 (13)0.0089 (14)
C90.0520 (11)0.0640 (15)0.0628 (14)0.0082 (11)0.0053 (10)0.0014 (11)
C150.0547 (13)0.085 (2)0.0785 (17)0.0023 (12)0.0225 (12)0.0165 (14)
C80.0558 (12)0.0678 (16)0.0552 (13)0.0112 (11)0.0019 (10)0.0020 (11)
C100.0529 (12)0.0734 (18)0.0745 (17)0.0109 (12)0.0122 (12)0.0091 (14)
C140.0718 (16)0.0621 (17)0.089 (2)0.0019 (13)0.0040 (14)0.0004 (14)
C10.0666 (16)0.103 (2)0.0833 (19)0.0119 (15)0.0289 (14)0.0008 (17)
C170.130 (3)0.090 (2)0.0701 (19)0.016 (2)0.0009 (18)0.0112 (16)
Geometric parameters (Å, º) top
O1—C21.377 (3)C2—C31.374 (3)
O1—C11.428 (3)C3—C41.362 (3)
O2—C31.369 (3)C4—H140.9300
O2—C11.408 (4)C16—C171.509 (4)
O3—C101.189 (3)C16—C151.524 (4)
O4—C101.382 (3)C16—H15A0.9700
O4—C111.396 (3)C16—H15B0.9700
O5—C111.192 (3)C9—C81.351 (3)
C7—C21.365 (3)C9—C101.477 (3)
C7—C61.403 (3)C15—H17A0.9700
C7—H20.9300C15—H17B0.9700
C13—C121.352 (3)C8—H180.9300
C13—C151.480 (4)C14—H20A0.9600
C13—C141.485 (4)C14—H20B0.9600
C12—C91.473 (3)C14—H20C0.9600
C12—C111.481 (4)C1—H21A0.9700
C5—C41.389 (3)C1—H21B0.9700
C5—C61.392 (3)C17—H22A0.9600
C5—H80.9300C17—H22B0.9600
C6—C81.465 (3)C17—H22C0.9600
C2—O1—C1105.7 (2)H15A—C16—H15B107.8
C3—O2—C1106.2 (2)C8—C9—C12135.8 (2)
C10—O4—C11110.5 (2)C8—C9—C10117.9 (2)
C2—C7—C6117.3 (2)C12—C9—C10105.3 (2)
C2—C7—H2121.3C13—C15—C16111.4 (2)
C6—C7—H2121.3C13—C15—H17A109.3
C12—C13—C15123.8 (3)C16—C15—H17A109.3
C12—C13—C14121.6 (2)C13—C15—H17B109.3
C15—C13—C14114.6 (2)C16—C15—H17B109.3
C13—C12—C9130.2 (2)H17A—C15—H17B108.0
C13—C12—C11123.8 (2)C9—C8—C6131.1 (2)
C9—C12—C11104.3 (2)C9—C8—H18114.5
C4—C5—C6121.9 (2)C6—C8—H18114.5
C4—C5—H8119.1O3—C10—O4120.7 (2)
C6—C5—H8119.1O3—C10—C9131.2 (3)
C5—C6—C7119.6 (2)O4—C10—C9108.1 (2)
C5—C6—C8122.3 (2)C13—C14—H20A109.5
C7—C6—C8118.0 (2)C13—C14—H20B109.5
C7—C2—C3122.5 (2)H20A—C14—H20B109.5
C7—C2—O1128.2 (2)C13—C14—H20C109.5
C3—C2—O1109.3 (2)H20A—C14—H20C109.5
C4—C3—O2128.2 (2)H20B—C14—H20C109.5
C4—C3—C2121.5 (2)O2—C1—O1108.6 (2)
O2—C3—C2110.2 (2)O2—C1—H21A110.0
O5—C11—O4119.7 (2)O1—C1—H21A110.0
O5—C11—C12132.6 (3)O2—C1—H21B110.0
O4—C11—C12107.7 (2)O1—C1—H21B110.0
C3—C4—C5117.2 (2)H21A—C1—H21B108.4
C3—C4—H14121.4C16—C17—H22A109.5
C5—C4—H14121.4C16—C17—H22B109.5
C17—C16—C15112.5 (2)H22A—C17—H22B109.5
C17—C16—H15A109.1C16—C17—H22C109.5
C15—C16—H15A109.1H22A—C17—H22C109.5
C17—C16—H15B109.1H22B—C17—H22C109.5
C15—C16—H15B109.1
C15—C13—C12—C9177.9 (2)C9—C12—C11—O418.3 (2)
C14—C13—C12—C92.9 (4)O2—C3—C4—C5178.3 (3)
C15—C13—C12—C1114.8 (4)C2—C3—C4—C52.1 (4)
C14—C13—C12—C11166.0 (2)C6—C5—C4—C31.0 (4)
C4—C5—C6—C70.9 (4)C13—C12—C9—C847.3 (5)
C4—C5—C6—C8176.0 (2)C11—C12—C9—C8147.2 (3)
C2—C7—C6—C51.6 (4)C13—C12—C9—C10145.7 (2)
C2—C7—C6—C8177.0 (2)C11—C12—C9—C1019.8 (2)
C6—C7—C2—C30.6 (4)C12—C13—C15—C1690.1 (3)
C6—C7—C2—O1178.6 (2)C14—C13—C15—C1689.1 (3)
C1—O1—C2—C7179.0 (3)C17—C16—C15—C13174.9 (3)
C1—O1—C2—C30.2 (3)C12—C9—C8—C66.4 (5)
C1—O2—C3—C4179.4 (3)C10—C9—C8—C6159.5 (3)
C1—O2—C3—C20.2 (3)C5—C6—C8—C920.4 (5)
C7—C2—C3—C41.4 (4)C7—C6—C8—C9164.4 (3)
O1—C2—C3—C4179.4 (2)C11—O4—C10—O3176.9 (3)
C7—C2—C3—O2179.0 (2)C11—O4—C10—C93.5 (3)
O1—C2—C3—O20.3 (3)C8—C9—C10—O324.7 (5)
C10—O4—C11—O5171.4 (2)C12—C9—C10—O3165.5 (3)
C10—O4—C11—C129.4 (3)C8—C9—C10—O4154.8 (2)
C13—C12—C11—O530.6 (4)C12—C9—C10—O415.0 (3)
C9—C12—C11—O5162.7 (3)C3—O2—C1—O10.1 (3)
C13—C12—C11—O4148.4 (2)C2—O1—C1—O20.1 (3)

Experimental details

Crystal data
Chemical formulaC17H16O5
Mr300.30
Crystal system, space groupMonoclinic, P21/c
Temperature (K)296
a, b, c (Å)7.8597 (11), 15.383 (3), 12.781 (2)
β (°) 105.117 (10)
V3)1491.8 (4)
Z4
Radiation typeMo Kα
µ (mm1)0.10
Crystal size (mm)0.30 × 0.25 × 0.15
Data collection
DiffractometerBruker APEX2 CCD area-detector
diffractometer
Absorption correctionMulti-scan
(APEX2 Software Suite; Bruker, 2005)
Tmin, Tmax0.971, 0.985
No. of measured, independent and
observed [I > 2.0σ(I)] reflections
14935, 3695, 2084
Rint0.024
(sin θ/λ)max1)0.670
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.056, 0.203, 0.94
No. of reflections3695
No. of parameters201
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.40, 0.16

Computer programs: APEX2 Software Suite (Bruker, 2005), APEX2 Software Suite, SIR97 (Altomare et al., 1999), SHELXL97 (Sheldrick, 1997), SHELXTL (Bruker, 1997), WinGX (Farrugia, 1999).

 

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