Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807023732/pv2014sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807023732/pv2014Isup2.hkl |
CCDC reference: 651530
Key indicators
- Single-crystal X-ray study
- T = 296 K
- Mean (C-C) = 0.004 Å
- R factor = 0.056
- wR factor = 0.203
- Data-to-parameter ratio = 18.4
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
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.
H atoms were positioned geometrically (C - H = 0.93 - 0.97 Å) and refined as riding, with Uiso(H) = 1.2Ueq(C).
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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].
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).
Fig. 1. The molecular structure of (I), showing the atom-numbering scheme with 50% probability displacement ellipsoids; H atoms have been omitted for clarity. |
C17H16O5 | F(000) = 632 |
Mr = 300.30 | Dx = 1.337 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 4386 reflections |
a = 7.8597 (11) Å | θ = 2.7–23.6° |
b = 15.383 (3) Å | µ = 0.10 mm−1 |
c = 12.781 (2) Å | T = 296 K |
β = 105.117 (10)° | Plate, yellow |
V = 1491.8 (4) Å3 | 0.30 × 0.25 × 0.15 mm |
Z = 4 |
Bruker APEX2 CCD area-detector diffractometer | 3695 independent reflections |
Radiation source: fine-focus sealed tube | 2084 reflections with I > 2.0σ(I) |
Graphite monochromator | Rint = 0.024 |
φ and ω scans | θmax = 28.4°, θmin = 2.1° |
Absorption correction: multi-scan (APEX2 Software Suite; Bruker, 2005) | h = −10→10 |
Tmin = 0.971, Tmax = 0.985 | k = −13→20 |
14935 measured reflections | l = −17→16 |
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)] = 0.056 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.203 | H-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 parameters | Δρmax = 0.40 e Å−3 |
0 restraints | Δρmin = −0.16 e Å−3 |
C17H16O5 | V = 1491.8 (4) Å3 |
Mr = 300.30 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 7.8597 (11) Å | µ = 0.10 mm−1 |
b = 15.383 (3) Å | T = 296 K |
c = 12.781 (2) Å | 0.30 × 0.25 × 0.15 mm |
β = 105.117 (10)° |
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 = 0.985 | Rint = 0.024 |
14935 measured reflections |
R[F2 > 2σ(F2)] = 0.056 | 0 restraints |
wR(F2) = 0.203 | H-atom parameters constrained |
S = 0.94 | Δρmax = 0.40 e Å−3 |
3695 reflections | Δρmin = −0.16 e Å−3 |
201 parameters |
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. |
x | y | z | Uiso*/Ueq | ||
O1 | −0.1718 (3) | 0.82579 (16) | 1.02559 (15) | 0.0841 (6) | |
O2 | −0.3854 (2) | 0.80813 (15) | 0.86514 (16) | 0.0836 (6) | |
O3 | 0.5532 (3) | 1.07745 (17) | 0.87030 (18) | 0.0974 (7) | |
O4 | 0.4746 (2) | 1.07754 (12) | 0.68911 (16) | 0.0727 (5) | |
O5 | 0.3415 (3) | 1.05288 (15) | 0.51414 (17) | 0.0840 (6) | |
C7 | 0.0484 (3) | 0.89375 (17) | 0.94481 (19) | 0.0605 (6) | |
H2 | 0.1334 | 0.9009 | 1.0101 | 0.073* | |
C13 | 0.2597 (3) | 0.87611 (18) | 0.6060 (2) | 0.0622 (6) | |
C12 | 0.2982 (3) | 0.95405 (16) | 0.65540 (19) | 0.0572 (6) | |
C5 | −0.0529 (3) | 0.90996 (17) | 0.75049 (19) | 0.0608 (6) | |
H8 | −0.0318 | 0.9280 | 0.6856 | 0.073* | |
C6 | 0.0795 (3) | 0.91969 (16) | 0.84621 (19) | 0.0569 (6) | |
C2 | −0.1117 (3) | 0.85766 (16) | 0.94102 (19) | 0.0587 (6) | |
C3 | −0.2401 (3) | 0.84713 (16) | 0.8457 (2) | 0.0592 (6) | |
C11 | 0.3643 (3) | 1.02957 (18) | 0.6057 (2) | 0.0655 (7) | |
C4 | −0.2156 (3) | 0.87400 (19) | 0.7491 (2) | 0.0661 (7) | |
H14 | −0.3041 | 0.8685 | 0.6850 | 0.079* | |
C16 | 0.0476 (3) | 0.87491 (19) | 0.4242 (2) | 0.0713 (7) | |
H15A | −0.0283 | 0.8385 | 0.4547 | 0.086* | |
H15B | 0.0143 | 0.9350 | 0.4309 | 0.086* | |
C9 | 0.3288 (3) | 0.97795 (17) | 0.7705 (2) | 0.0614 (6) | |
C15 | 0.2383 (3) | 0.8619 (2) | 0.4888 (2) | 0.0719 (7) | |
H17A | 0.2752 | 0.8033 | 0.4773 | 0.086* | |
H17B | 0.3133 | 0.9021 | 0.4630 | 0.086* | |
C8 | 0.2473 (3) | 0.96253 (17) | 0.8495 (2) | 0.0619 (6) | |
H18 | 0.3080 | 0.9825 | 0.9176 | 0.074* | |
C10 | 0.4634 (3) | 1.04727 (19) | 0.7889 (2) | 0.0678 (7) | |
C14 | 0.2331 (4) | 0.79731 (18) | 0.6670 (2) | 0.0775 (8) | |
H20A | 0.2687 | 0.8093 | 0.7434 | 0.116* | |
H20B | 0.3026 | 0.7504 | 0.6507 | 0.116* | |
H20C | 0.1108 | 0.7813 | 0.6464 | 0.116* | |
C1 | −0.3455 (4) | 0.7941 (2) | 0.9778 (3) | 0.0824 (8) | |
H21A | −0.3519 | 0.7326 | 0.9928 | 0.099* | |
H21B | −0.4298 | 0.8245 | 1.0081 | 0.099* | |
C17 | 0.0189 (6) | 0.8531 (2) | 0.3058 (2) | 0.1014 (11) | |
H22A | 0.0941 | 0.8887 | 0.2753 | 0.152* | |
H22B | −0.1020 | 0.8637 | 0.2682 | 0.152* | |
H22C | 0.0462 | 0.7929 | 0.2985 | 0.152* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0716 (11) | 0.1183 (17) | 0.0632 (11) | −0.0185 (11) | 0.0189 (9) | 0.0098 (11) |
O2 | 0.0510 (9) | 0.1139 (17) | 0.0833 (13) | −0.0151 (10) | 0.0127 (8) | 0.0099 (11) |
O3 | 0.0794 (13) | 0.1191 (19) | 0.0881 (14) | −0.0453 (13) | 0.0117 (11) | −0.0243 (13) |
O4 | 0.0639 (10) | 0.0713 (12) | 0.0861 (13) | −0.0182 (9) | 0.0252 (9) | −0.0034 (10) |
O5 | 0.0748 (12) | 0.1033 (16) | 0.0788 (13) | −0.0082 (11) | 0.0288 (10) | 0.0186 (11) |
C7 | 0.0569 (12) | 0.0686 (16) | 0.0497 (12) | −0.0075 (11) | 0.0028 (10) | 0.0000 (11) |
C13 | 0.0421 (10) | 0.0699 (17) | 0.0715 (15) | −0.0003 (10) | 0.0090 (10) | −0.0049 (12) |
C12 | 0.0437 (10) | 0.0632 (15) | 0.0637 (14) | −0.0021 (10) | 0.0120 (9) | 0.0017 (11) |
C5 | 0.0562 (12) | 0.0693 (16) | 0.0525 (13) | −0.0033 (11) | 0.0067 (10) | 0.0061 (11) |
C6 | 0.0544 (12) | 0.0571 (14) | 0.0549 (13) | −0.0060 (10) | 0.0065 (10) | 0.0023 (10) |
C2 | 0.0573 (12) | 0.0636 (15) | 0.0547 (13) | −0.0010 (11) | 0.0137 (10) | 0.0038 (11) |
C3 | 0.0455 (11) | 0.0631 (15) | 0.0667 (14) | −0.0002 (10) | 0.0102 (10) | 0.0014 (11) |
C11 | 0.0480 (11) | 0.0743 (18) | 0.0766 (17) | −0.0036 (11) | 0.0207 (11) | −0.0002 (14) |
C4 | 0.0494 (11) | 0.0827 (19) | 0.0587 (14) | 0.0002 (12) | 0.0009 (10) | 0.0032 (12) |
C16 | 0.0633 (14) | 0.0708 (18) | 0.0796 (18) | 0.0047 (12) | 0.0182 (13) | −0.0089 (14) |
C9 | 0.0520 (11) | 0.0640 (15) | 0.0628 (14) | −0.0082 (11) | 0.0053 (10) | 0.0014 (11) |
C15 | 0.0547 (13) | 0.085 (2) | 0.0785 (17) | −0.0023 (12) | 0.0225 (12) | −0.0165 (14) |
C8 | 0.0558 (12) | 0.0678 (16) | 0.0552 (13) | −0.0112 (11) | 0.0019 (10) | 0.0020 (11) |
C10 | 0.0529 (12) | 0.0734 (18) | 0.0745 (17) | −0.0109 (12) | 0.0122 (12) | −0.0091 (14) |
C14 | 0.0718 (16) | 0.0621 (17) | 0.089 (2) | −0.0019 (13) | 0.0040 (14) | 0.0004 (14) |
C1 | 0.0666 (16) | 0.103 (2) | 0.0833 (19) | −0.0119 (15) | 0.0289 (14) | −0.0008 (17) |
C17 | 0.130 (3) | 0.090 (2) | 0.0701 (19) | 0.016 (2) | 0.0009 (18) | −0.0112 (16) |
O1—C2 | 1.377 (3) | C2—C3 | 1.374 (3) |
O1—C1 | 1.428 (3) | C3—C4 | 1.362 (3) |
O2—C3 | 1.369 (3) | C4—H14 | 0.9300 |
O2—C1 | 1.408 (4) | C16—C17 | 1.509 (4) |
O3—C10 | 1.189 (3) | C16—C15 | 1.524 (4) |
O4—C10 | 1.382 (3) | C16—H15A | 0.9700 |
O4—C11 | 1.396 (3) | C16—H15B | 0.9700 |
O5—C11 | 1.192 (3) | C9—C8 | 1.351 (3) |
C7—C2 | 1.365 (3) | C9—C10 | 1.477 (3) |
C7—C6 | 1.403 (3) | C15—H17A | 0.9700 |
C7—H2 | 0.9300 | C15—H17B | 0.9700 |
C13—C12 | 1.352 (3) | C8—H18 | 0.9300 |
C13—C15 | 1.480 (4) | C14—H20A | 0.9600 |
C13—C14 | 1.485 (4) | C14—H20B | 0.9600 |
C12—C9 | 1.473 (3) | C14—H20C | 0.9600 |
C12—C11 | 1.481 (4) | C1—H21A | 0.9700 |
C5—C4 | 1.389 (3) | C1—H21B | 0.9700 |
C5—C6 | 1.392 (3) | C17—H22A | 0.9600 |
C5—H8 | 0.9300 | C17—H22B | 0.9600 |
C6—C8 | 1.465 (3) | C17—H22C | 0.9600 |
C2—O1—C1 | 105.7 (2) | H15A—C16—H15B | 107.8 |
C3—O2—C1 | 106.2 (2) | C8—C9—C12 | 135.8 (2) |
C10—O4—C11 | 110.5 (2) | C8—C9—C10 | 117.9 (2) |
C2—C7—C6 | 117.3 (2) | C12—C9—C10 | 105.3 (2) |
C2—C7—H2 | 121.3 | C13—C15—C16 | 111.4 (2) |
C6—C7—H2 | 121.3 | C13—C15—H17A | 109.3 |
C12—C13—C15 | 123.8 (3) | C16—C15—H17A | 109.3 |
C12—C13—C14 | 121.6 (2) | C13—C15—H17B | 109.3 |
C15—C13—C14 | 114.6 (2) | C16—C15—H17B | 109.3 |
C13—C12—C9 | 130.2 (2) | H17A—C15—H17B | 108.0 |
C13—C12—C11 | 123.8 (2) | C9—C8—C6 | 131.1 (2) |
C9—C12—C11 | 104.3 (2) | C9—C8—H18 | 114.5 |
C4—C5—C6 | 121.9 (2) | C6—C8—H18 | 114.5 |
C4—C5—H8 | 119.1 | O3—C10—O4 | 120.7 (2) |
C6—C5—H8 | 119.1 | O3—C10—C9 | 131.2 (3) |
C5—C6—C7 | 119.6 (2) | O4—C10—C9 | 108.1 (2) |
C5—C6—C8 | 122.3 (2) | C13—C14—H20A | 109.5 |
C7—C6—C8 | 118.0 (2) | C13—C14—H20B | 109.5 |
C7—C2—C3 | 122.5 (2) | H20A—C14—H20B | 109.5 |
C7—C2—O1 | 128.2 (2) | C13—C14—H20C | 109.5 |
C3—C2—O1 | 109.3 (2) | H20A—C14—H20C | 109.5 |
C4—C3—O2 | 128.2 (2) | H20B—C14—H20C | 109.5 |
C4—C3—C2 | 121.5 (2) | O2—C1—O1 | 108.6 (2) |
O2—C3—C2 | 110.2 (2) | O2—C1—H21A | 110.0 |
O5—C11—O4 | 119.7 (2) | O1—C1—H21A | 110.0 |
O5—C11—C12 | 132.6 (3) | O2—C1—H21B | 110.0 |
O4—C11—C12 | 107.7 (2) | O1—C1—H21B | 110.0 |
C3—C4—C5 | 117.2 (2) | H21A—C1—H21B | 108.4 |
C3—C4—H14 | 121.4 | C16—C17—H22A | 109.5 |
C5—C4—H14 | 121.4 | C16—C17—H22B | 109.5 |
C17—C16—C15 | 112.5 (2) | H22A—C17—H22B | 109.5 |
C17—C16—H15A | 109.1 | C16—C17—H22C | 109.5 |
C15—C16—H15A | 109.1 | H22A—C17—H22C | 109.5 |
C17—C16—H15B | 109.1 | H22B—C17—H22C | 109.5 |
C15—C16—H15B | 109.1 | ||
C15—C13—C12—C9 | −177.9 (2) | C9—C12—C11—O4 | 18.3 (2) |
C14—C13—C12—C9 | 2.9 (4) | O2—C3—C4—C5 | −178.3 (3) |
C15—C13—C12—C11 | −14.8 (4) | C2—C3—C4—C5 | 2.1 (4) |
C14—C13—C12—C11 | 166.0 (2) | C6—C5—C4—C3 | −1.0 (4) |
C4—C5—C6—C7 | −0.9 (4) | C13—C12—C9—C8 | −47.3 (5) |
C4—C5—C6—C8 | −176.0 (2) | C11—C12—C9—C8 | 147.2 (3) |
C2—C7—C6—C5 | 1.6 (4) | C13—C12—C9—C10 | 145.7 (2) |
C2—C7—C6—C8 | 177.0 (2) | C11—C12—C9—C10 | −19.8 (2) |
C6—C7—C2—C3 | −0.6 (4) | C12—C13—C15—C16 | −90.1 (3) |
C6—C7—C2—O1 | 178.6 (2) | C14—C13—C15—C16 | 89.1 (3) |
C1—O1—C2—C7 | −179.0 (3) | C17—C16—C15—C13 | −174.9 (3) |
C1—O1—C2—C3 | 0.2 (3) | C12—C9—C8—C6 | −6.4 (5) |
C1—O2—C3—C4 | −179.4 (3) | C10—C9—C8—C6 | 159.5 (3) |
C1—O2—C3—C2 | 0.2 (3) | C5—C6—C8—C9 | −20.4 (5) |
C7—C2—C3—C4 | −1.4 (4) | C7—C6—C8—C9 | 164.4 (3) |
O1—C2—C3—C4 | 179.4 (2) | C11—O4—C10—O3 | 176.9 (3) |
C7—C2—C3—O2 | 179.0 (2) | C11—O4—C10—C9 | −3.5 (3) |
O1—C2—C3—O2 | −0.3 (3) | C8—C9—C10—O3 | 24.7 (5) |
C10—O4—C11—O5 | 171.4 (2) | C12—C9—C10—O3 | −165.5 (3) |
C10—O4—C11—C12 | −9.4 (3) | C8—C9—C10—O4 | −154.8 (2) |
C13—C12—C11—O5 | 30.6 (4) | C12—C9—C10—O4 | 15.0 (3) |
C9—C12—C11—O5 | −162.7 (3) | C3—O2—C1—O1 | −0.1 (3) |
C13—C12—C11—O4 | −148.4 (2) | C2—O1—C1—O2 | −0.1 (3) |
Experimental details
Crystal data | |
Chemical formula | C17H16O5 |
Mr | 300.30 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 296 |
a, b, c (Å) | 7.8597 (11), 15.383 (3), 12.781 (2) |
β (°) | 105.117 (10) |
V (Å3) | 1491.8 (4) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.10 |
Crystal size (mm) | 0.30 × 0.25 × 0.15 |
Data collection | |
Diffractometer | Bruker APEX2 CCD area-detector diffractometer |
Absorption correction | Multi-scan (APEX2 Software Suite; Bruker, 2005) |
Tmin, Tmax | 0.971, 0.985 |
No. of measured, independent and observed [I > 2.0σ(I)] reflections | 14935, 3695, 2084 |
Rint | 0.024 |
(sin θ/λ)max (Å−1) | 0.670 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.056, 0.203, 0.94 |
No. of reflections | 3695 |
No. of parameters | 201 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 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).
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).