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3-Furylfulgides are photochromic compounds showing high thermal stability in their closed forms. However, their photochromic properties in the solid state should be improved further to fabricate molecular devices. Understanding how the size and the flexibility of the non-aromatic alkylidene moiety alter the crystalline state photochromic properties is also important here, as the alkylidene group is directly involved in the photochromic ring closing and opening reactions. The synthesis of four 3-furylfulgides composed of different alkylidene groups (rigid isopropyl, flexible 2-butyl, rigid cyclopentyl and flexible cyclohexyl), their crystal structures and structure-photochromic property correlation in the crystalline state are reported here. Crystallographic data along with reaction cavity volumes calculated using the program CAVITY [Ohashi et al. (1981), J. Am. Chem. Soc. 103, 5805-5812] disclosed that fulgides with flexible groups at the ring closing site have more free volume around the reactive area in the crystal lattice, which can provide more space for the atomic movements in the reaction and flexibility can reduce the strain built up in the closed C-isomers by making conformations. According to UV-vis spectroscopic data, a higher yield of C-isomers and a better fatigue resistance were obtained for the 3-furylfulgide with the largest and flexible cyclohexyl group showing greater photochromic properties in the crystalline state than the fulgide containing the smallest and rigid isopropyl group.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S2052520615015267/gw5039sup1.cif
Contains datablocks 1E, 2E, 3E, 4E, publication_text

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2052520615015267/gw50391Esup2.hkl
Contains datablock 1E

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2052520615015267/gw50392Esup3.hkl
Contains datablock 2E

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2052520615015267/gw50393Esup4.hkl
Contains datablock 3E

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2052520615015267/gw50394Esup5.hkl
Contains datablock 4E

pdf

Portable Document Format (PDF) file https://doi.org/10.1107/S2052520615015267/gw5039sup6.pdf
Supporting figures

CCDC references: 1010419; 1010420; 1010421; 1010422

Computing details top

For all compounds, data collection: PROCESS-AUTO (Rigaku, 1998); cell refinement: PROCESS-AUTO; data reduction: TEXSAN (Rigaku, 1999). Program(s) used to solve structure: SHELXS97 (Sheldrick, 2008) for (1E); SHELXS97 (Sheldrick, 1990) for (2E), (4E); SHELXL97 (Sheldrick, 2008) for (3E). For all compounds, program(s) used to refine structure: SHELXL2013 (Sheldrick, 2013). Software used to prepare material for publication: SHELXL97 for (1E), (2E); SHELXL97 (Sheldrick, 2008) for (3E), (4E).

Figures top
[Figure 1]
[Figure 2]
[Figure 3]
(1E) 3-furylfulgide with isopropylidene-1E top
Crystal data top
C15H16O4F(000) = 552
Mr = 260.28Dx = 1.300 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71075 Å
a = 12.560 (7) ÅCell parameters from 2346 reflections
b = 7.667 (5) Åθ = 3.0–27.6°
c = 14.624 (9) ŵ = 0.09 mm1
β = 109.259 (16)°T = 173 K
V = 1329.5 (15) Å3Diamond, orange
Z = 40.18 × 0.10 × 0.10 mm
Data collection top
Rigaku RAXIS-RAPID Imaging Plate
diffractometer
2258 reflections with I > 2σ(I)
Oscillation Photograph scansRint = 0.023
Absorption correction: multi-scan
ABSCOR (Higashi, 1995)
θmax = 27.5°, θmin = 3.0°
Tmin = 0.814, Tmax = 0.942h = 1616
12492 measured reflectionsk = 99
3032 independent reflectionsl = 1818
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)] = 0.048Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.141H-atom parameters constrained
S = 1.08 w = 1/[σ2(Fo2) + (0.0861P)2 + 0.1234P]
where P = (Fo2 + 2Fc2)/3
3032 reflections(Δ/σ)max = 0.001
177 parametersΔρmax = 0.34 e Å3
1 restraintΔρmin = 0.24 e Å3
Crystal data top
C15H16O4V = 1329.5 (15) Å3
Mr = 260.28Z = 4
Monoclinic, P21/nMo Kα radiation
a = 12.560 (7) ŵ = 0.09 mm1
b = 7.667 (5) ÅT = 173 K
c = 14.624 (9) Å0.18 × 0.10 × 0.10 mm
β = 109.259 (16)°
Data collection top
Rigaku RAXIS-RAPID Imaging Plate
diffractometer
3032 independent reflections
Absorption correction: multi-scan
ABSCOR (Higashi, 1995)
2258 reflections with I > 2σ(I)
Tmin = 0.814, Tmax = 0.942Rint = 0.023
12492 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0481 restraint
wR(F2) = 0.141H-atom parameters constrained
S = 1.08Δρmax = 0.34 e Å3
3032 reflectionsΔρmin = 0.24 e Å3
177 parameters
Special details top

Experimental. 3-furylfugide with isopropylidene-1E

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
C120.35124 (12)0.2992 (2)0.38698 (11)0.0352 (4)
O10.20753 (11)0.3115 (2)0.09531 (9)0.0607 (4)
O20.39117 (10)0.31867 (17)0.07495 (8)0.0452 (3)
O30.57910 (11)0.31103 (19)0.01869 (9)0.0517 (4)
O40.44208 (8)0.38865 (14)0.37705 (7)0.0325 (3)
C10.30152 (15)0.2946 (2)0.04044 (11)0.0416 (4)
C20.34760 (13)0.2559 (2)0.06423 (10)0.0325 (3)
C30.46785 (13)0.21904 (19)0.08324 (10)0.0323 (3)
C40.49306 (15)0.2866 (2)0.00229 (12)0.0389 (4)
C50.54002 (13)0.1160 (2)0.14982 (11)0.0347 (3)
C60.66243 (14)0.0989 (3)0.15835 (14)0.0495 (5)
H6A0.66880.08950.09350.074*
H6B0.69420.00570.19590.074*
H6C0.70390.20200.19110.074*
C70.50383 (14)0.0090 (2)0.21955 (12)0.0405 (4)
H7A0.52910.06510.28330.061*
H7B0.53720.10760.22450.061*
H7C0.42140.00070.19660.061*
C80.28639 (12)0.28179 (19)0.12470 (10)0.0316 (3)
C90.15964 (13)0.3004 (2)0.08688 (12)0.0415 (4)
H9A0.13370.30460.01590.062*
H9B0.13780.40820.11210.062*
H9C0.12510.20040.10810.062*
C100.33577 (12)0.30032 (19)0.22981 (10)0.0295 (3)
C110.43111 (11)0.38823 (19)0.28075 (10)0.0286 (3)
C130.28431 (12)0.2456 (2)0.29990 (11)0.0346 (3)
H130.21560.18310.28670.042*
C140.51761 (12)0.4895 (2)0.25533 (11)0.0353 (3)
H14A0.58390.41590.26330.053*
H14B0.53950.59130.29800.053*
H14C0.48680.52830.18790.053*
C150.34712 (16)0.2848 (3)0.48690 (12)0.0500 (5)
H15A0.27570.23080.48510.075*
H15B0.35280.40140.51560.075*
H15C0.41010.21280.52600.075*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C120.0292 (7)0.0429 (9)0.0366 (8)0.0034 (6)0.0148 (6)0.0014 (6)
O10.0478 (7)0.0900 (11)0.0331 (6)0.0038 (7)0.0017 (6)0.0012 (6)
O20.0518 (7)0.0536 (8)0.0302 (6)0.0018 (6)0.0134 (5)0.0016 (5)
O30.0515 (7)0.0627 (9)0.0493 (7)0.0038 (6)0.0281 (6)0.0021 (6)
O40.0313 (5)0.0387 (6)0.0282 (5)0.0051 (4)0.0109 (4)0.0038 (4)
C10.0449 (9)0.0454 (10)0.0304 (8)0.0016 (7)0.0069 (7)0.0039 (7)
C20.0340 (7)0.0319 (8)0.0275 (7)0.0042 (6)0.0047 (6)0.0024 (6)
C30.0358 (7)0.0321 (7)0.0290 (7)0.0033 (6)0.0109 (6)0.0051 (6)
C40.0457 (8)0.0383 (8)0.0344 (7)0.0037 (7)0.0155 (7)0.0057 (6)
C50.0362 (8)0.0335 (8)0.0344 (7)0.0003 (6)0.0116 (6)0.0076 (6)
C60.0377 (9)0.0587 (12)0.0522 (10)0.0085 (8)0.0150 (8)0.0052 (8)
C70.0439 (8)0.0345 (8)0.0409 (8)0.0052 (7)0.0108 (7)0.0026 (7)
C80.0296 (7)0.0302 (7)0.0315 (7)0.0033 (5)0.0056 (6)0.0025 (6)
C90.0315 (8)0.0487 (10)0.0390 (8)0.0039 (7)0.0047 (7)0.0045 (7)
C100.0279 (7)0.0282 (7)0.0322 (7)0.0003 (5)0.0094 (6)0.0010 (5)
C110.0287 (7)0.0296 (7)0.0269 (6)0.0004 (5)0.0083 (5)0.0011 (5)
C130.0287 (7)0.0379 (8)0.0387 (8)0.0049 (6)0.0131 (6)0.0018 (6)
C140.0360 (8)0.0375 (8)0.0322 (7)0.0099 (6)0.0108 (6)0.0025 (6)
C150.0461 (9)0.0728 (13)0.0371 (9)0.0122 (9)0.0217 (8)0.0048 (8)
Geometric parameters (Å, º) top
C12—C131.338 (2)C7—H7A0.9800
C12—O41.3794 (18)C7—H7B0.9800
C12—C151.483 (2)C7—H7C0.9800
O1—C11.196 (2)C8—C101.462 (2)
O2—C41.389 (2)C8—C91.510 (2)
O2—C11.390 (2)C9—H9A0.9800
O3—C41.197 (2)C9—H9B0.9800
O4—C111.3690 (18)C9—H9C0.9800
C1—C21.477 (2)C10—C111.362 (2)
C2—C81.364 (2)C10—C131.443 (2)
C2—C31.470 (2)C11—C141.479 (2)
C3—C51.346 (2)C13—H130.9500
C3—C41.481 (2)C14—H14A0.9800
C5—C71.491 (2)C14—H14B0.9800
C5—C61.507 (2)C14—H14C0.9800
C6—H6A0.9800C15—H15A0.9800
C6—H6B0.9800C15—H15B0.9800
C6—H6C0.9800C15—H15C0.9800
C13—C12—O4109.52 (13)H7B—C7—H7C109.5
C13—C12—C15134.40 (15)C2—C8—C10124.14 (14)
O4—C12—C15116.08 (13)C2—C8—C9121.85 (14)
C4—O2—C1110.55 (13)C10—C8—C9113.98 (13)
C11—O4—C12107.53 (11)C8—C9—H9A109.5
O1—C1—O2118.74 (16)C8—C9—H9B109.5
O1—C1—C2132.84 (17)H9A—C9—H9B109.5
O2—C1—C2108.39 (14)C8—C9—H9C109.5
C8—C2—C3131.98 (14)H9A—C9—H9C109.5
C8—C2—C1122.04 (15)H9B—C9—H9C109.5
C3—C2—C1105.16 (13)C11—C10—C13105.93 (13)
C5—C3—C2130.86 (14)C11—C10—C8127.92 (13)
C5—C3—C4122.38 (15)C13—C10—C8125.77 (13)
C2—C3—C4105.40 (13)C10—C11—O4109.62 (12)
O3—C4—O2118.95 (16)C10—C11—C14135.12 (14)
O3—C4—C3133.07 (17)O4—C11—C14115.11 (12)
O2—C4—C3107.95 (14)C12—C13—C10107.40 (14)
C3—C5—C7122.20 (15)C12—C13—H13126.3
C3—C5—C6122.41 (15)C10—C13—H13126.3
C7—C5—C6115.38 (14)C11—C14—H14A109.5
C5—C6—H6A109.5C11—C14—H14B109.5
C5—C6—H6B109.5H14A—C14—H14B109.5
H6A—C6—H6B109.5C11—C14—H14C109.5
C5—C6—H6C109.5H14A—C14—H14C109.5
H6A—C6—H6C109.5H14B—C14—H14C109.5
H6B—C6—H6C109.5C12—C15—H15A109.5
C5—C7—H7A109.5C12—C15—H15B109.5
C5—C7—H7B109.5H15A—C15—H15B109.5
H7A—C7—H7B109.5C12—C15—H15C109.5
C5—C7—H7C109.5H15A—C15—H15C109.5
H7A—C7—H7C109.5H15B—C15—H15C109.5
C13—C12—O4—C110.70 (17)C2—C3—C5—C6178.79 (15)
C15—C12—O4—C11179.92 (14)C4—C3—C5—C616.6 (2)
C4—O2—C1—O1177.51 (16)C3—C2—C8—C108.5 (3)
C4—O2—C1—C24.22 (18)C1—C2—C8—C10159.55 (15)
O1—C1—C2—C819.9 (3)C3—C2—C8—C9173.80 (16)
O2—C1—C2—C8158.01 (15)C1—C2—C8—C918.2 (2)
O1—C1—C2—C3169.3 (2)C2—C8—C10—C1140.0 (2)
O2—C1—C2—C312.78 (17)C9—C8—C10—C11137.88 (16)
C8—C2—C3—C539.8 (3)C2—C8—C10—C13148.17 (16)
C1—C2—C3—C5150.70 (17)C9—C8—C10—C1333.9 (2)
C8—C2—C3—C4153.59 (17)C13—C10—C11—O40.87 (16)
C1—C2—C3—C415.89 (16)C8—C10—C11—O4173.97 (13)
C1—O2—C4—O3175.88 (16)C13—C10—C11—C14174.18 (16)
C1—O2—C4—C36.14 (18)C8—C10—C11—C141.1 (3)
C5—C3—C4—O323.5 (3)C12—O4—C11—C100.16 (16)
C2—C3—C4—O3168.50 (19)C12—O4—C11—C14175.99 (13)
C5—C3—C4—O2154.10 (15)O4—C12—C13—C101.22 (18)
C2—C3—C4—O213.92 (16)C15—C12—C13—C10179.76 (19)
C2—C3—C5—C71.9 (3)C11—C10—C13—C121.29 (17)
C4—C3—C5—C7162.72 (14)C8—C10—C13—C12174.58 (14)
(2E) 3-furylfulgide with-2-butylidene-2E top
Crystal data top
C16H18O4F(000) = 584
Mr = 274.30Dx = 1.269 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71075 Å
a = 12.6826 (9) ÅCell parameters from 9442 reflections
b = 7.9499 (6) Åθ = 3.1–30.5°
c = 14.9392 (11) ŵ = 0.09 mm1
β = 107.531 (2)°T = 173 K
V = 1436.29 (18) Å3Rods, yellow
Z = 40.13 × 0.09 × 0.03 mm
Data collection top
Rigaku RAXIS-RAPID Imaging Plate
diffractometer
1772 reflections with I > 2σ(I)
Oscillation Photograph scansRint = 0.052
Absorption correction: multi-scan
ABSCOR (Higashi, 1995)
θmax = 27.5°, θmin = 3.1°
Tmin = 0.886, Tmax = 0.946h = 1516
13610 measured reflectionsk = 1010
3305 independent reflectionsl = 1919
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)] = 0.061H-atom parameters constrained
wR(F2) = 0.207 w = 1/[σ2(Fo2) + (0.1169P)2]
where P = (Fo2 + 2Fc2)/3
S = 1.01(Δ/σ)max < 0.001
3305 reflectionsΔρmax = 0.24 e Å3
201 parametersΔρmin = 0.24 e Å3
1 restraintExtinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.016 (5)
Crystal data top
C16H18O4V = 1436.29 (18) Å3
Mr = 274.30Z = 4
Monoclinic, P21/nMo Kα radiation
a = 12.6826 (9) ŵ = 0.09 mm1
b = 7.9499 (6) ÅT = 173 K
c = 14.9392 (11) Å0.13 × 0.09 × 0.03 mm
β = 107.531 (2)°
Data collection top
Rigaku RAXIS-RAPID Imaging Plate
diffractometer
3305 independent reflections
Absorption correction: multi-scan
ABSCOR (Higashi, 1995)
1772 reflections with I > 2σ(I)
Tmin = 0.886, Tmax = 0.946Rint = 0.052
13610 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0611 restraint
wR(F2) = 0.207H-atom parameters constrained
S = 1.01Δρmax = 0.24 e Å3
3305 reflectionsΔρmin = 0.24 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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
O10.18822 (17)0.3387 (4)0.08316 (15)0.0893 (8)
C10.4688 (2)0.2975 (3)0.00784 (17)0.0530 (6)
O20.36756 (15)0.3378 (2)0.07351 (12)0.0608 (5)
C20.4470 (2)0.2337 (3)0.07742 (17)0.0491 (6)
O30.55203 (16)0.3155 (2)0.02922 (13)0.0641 (5)
C30.3299 (2)0.2755 (3)0.06657 (17)0.0507 (6)
O40.42893 (13)0.3929 (2)0.37383 (11)0.0514 (5)
C40.2817 (2)0.3174 (4)0.03401 (19)0.0617 (7)
C50.2721 (2)0.2995 (3)0.12939 (18)0.0496 (6)
C60.1475 (2)0.3200 (4)0.0978 (2)0.0617 (7)
H6A0.11930.30670.02950.093*
H6B0.12840.43220.11520.093*
H6C0.11440.23440.12810.093*
C70.32192 (18)0.3129 (3)0.23120 (16)0.0463 (6)
C100.41742 (18)0.3940 (3)0.27924 (17)0.0470 (6)
C90.3387 (2)0.3096 (3)0.38577 (18)0.0520 (6)
C80.2721 (2)0.2613 (3)0.30193 (18)0.0518 (6)
H80.20390.20310.29090.062*
C110.5039 (2)0.4892 (3)0.25283 (19)0.0560 (7)
H11A0.56840.41670.25970.084*
H11B0.52570.58750.29380.084*
H11C0.47480.52630.18740.084*
C120.3348 (2)0.2954 (4)0.4840 (2)0.0699 (8)
H12A0.26320.24890.48390.105*
H12B0.34440.40700.51320.105*
H12C0.39420.22090.51970.105*
C130.5179 (2)0.1271 (3)0.13674 (17)0.0538 (6)
C140.6333 (2)0.0937 (4)0.1321 (2)0.0675 (8)
H14A0.65840.01720.16090.081*0.7
H14B0.63150.08810.06540.081*0.7
H14C0.63010.06380.06770.101*0.22
H14D0.66620.00060.17430.101*0.22
H14E0.67860.19490.15120.101*0.22
H14F0.63070.02290.07690.081*0.08
H14G0.67090.20070.12690.081*0.08
C160.4869 (2)0.0293 (4)0.2115 (2)0.0646 (7)
H16A0.53140.06850.27360.097*0.78
H16B0.50090.09070.20500.097*0.78
H16C0.40830.04640.20450.097*0.78
H16D0.48130.10360.26300.077*0.22
H16E0.41610.03110.18520.077*0.22
C150.7138 (3)0.2232 (5)0.1802 (3)0.0580 (10)0.7
H15A0.68950.33340.15220.087*0.7
H15B0.78650.19660.17350.087*0.7
H15C0.71890.22550.24700.087*0.7
C170.5772 (11)0.0852 (17)0.2428 (11)0.073 (4)*0.22
H17A0.56050.18860.20550.109*0.22
H17B0.58910.11190.30920.109*0.22
H17C0.64420.03350.23530.109*0.22
C180.6921 (17)0.007 (3)0.2186 (11)0.031 (5)*0.08
H18A0.72160.08920.26860.046*0.08
H18B0.75300.05890.20870.046*0.08
H18C0.64100.06900.23680.046*0.08
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0675 (13)0.142 (2)0.0474 (12)0.0004 (13)0.0010 (10)0.0071 (13)
C10.0604 (15)0.0667 (15)0.0358 (13)0.0013 (12)0.0201 (12)0.0008 (11)
O20.0715 (12)0.0766 (12)0.0342 (9)0.0007 (10)0.0158 (9)0.0037 (8)
C20.0544 (14)0.0591 (14)0.0365 (13)0.0033 (11)0.0178 (11)0.0022 (11)
O30.0759 (12)0.0793 (13)0.0464 (11)0.0014 (10)0.0324 (10)0.0058 (9)
C30.0522 (13)0.0616 (14)0.0370 (13)0.0071 (11)0.0116 (11)0.0000 (11)
O40.0507 (9)0.0707 (11)0.0378 (9)0.0055 (8)0.0208 (7)0.0058 (8)
C40.0624 (16)0.0774 (18)0.0421 (15)0.0034 (14)0.0111 (13)0.0017 (13)
C50.0476 (12)0.0573 (14)0.0442 (14)0.0032 (11)0.0143 (11)0.0003 (11)
C60.0489 (13)0.0805 (18)0.0547 (16)0.0050 (13)0.0138 (12)0.0023 (14)
C70.0436 (11)0.0586 (13)0.0395 (13)0.0032 (10)0.0168 (10)0.0003 (11)
C100.0466 (12)0.0616 (14)0.0379 (13)0.0009 (11)0.0201 (10)0.0014 (11)
C90.0502 (13)0.0674 (15)0.0450 (14)0.0003 (12)0.0246 (11)0.0023 (12)
C80.0488 (13)0.0629 (14)0.0493 (15)0.0031 (11)0.0232 (12)0.0011 (12)
C110.0537 (14)0.0728 (16)0.0460 (14)0.0127 (13)0.0219 (12)0.0061 (13)
C120.0687 (18)0.103 (2)0.0474 (16)0.0059 (16)0.0324 (14)0.0003 (15)
C130.0589 (15)0.0675 (15)0.0389 (13)0.0040 (12)0.0208 (12)0.0010 (11)
C140.0710 (18)0.0850 (19)0.0557 (17)0.0184 (15)0.0329 (14)0.0125 (15)
C160.0757 (17)0.0739 (18)0.0516 (16)0.0135 (15)0.0306 (14)0.0160 (14)
C150.0474 (19)0.086 (3)0.045 (2)0.0088 (18)0.0206 (16)0.0034 (19)
Geometric parameters (Å, º) top
O1—C41.204 (3)C12—H12C0.9800
C1—O31.200 (3)C13—C161.507 (4)
C1—O21.398 (3)C13—C141.511 (4)
C1—C21.472 (3)C14—C181.458 (10)
O2—C41.396 (3)C14—C151.476 (5)
C2—C131.353 (3)C14—H14A0.9900
C2—C31.483 (3)C14—H14B0.9900
C3—C51.367 (3)C14—H14C0.9800
C3—C41.480 (4)C14—H14D0.9800
O4—C101.376 (3)C14—H14E0.9800
O4—C91.380 (3)C14—H14F0.9900
C5—C71.465 (3)C14—H14G0.9900
C5—C61.515 (3)C16—C171.427 (13)
C6—H6A0.9800C16—H16A0.9800
C6—H6B0.9800C16—H16B0.9800
C6—H6C0.9800C16—H16C0.9800
C7—C101.369 (3)C16—H16D0.9900
C7—C81.445 (3)C16—H16E0.9900
C10—C111.480 (3)C15—H15A0.9800
C9—C81.339 (4)C15—H15B0.9800
C9—C121.488 (4)C15—H15C0.9800
C8—H80.9500C17—H17A0.9800
C11—H11A0.9800C17—H17B0.9800
C11—H11B0.9800C17—H17C0.9800
C11—H11C0.9800C18—H18A0.9800
C12—H12A0.9800C18—H18B0.9800
C12—H12B0.9800C18—H18C0.9800
O3—C1—O2118.8 (2)C16—C13—C14114.6 (2)
O3—C1—C2132.9 (2)C18—C14—C13106.6 (9)
O2—C1—C2108.3 (2)C15—C14—C13113.1 (3)
C4—O2—C1110.2 (2)C15—C14—H14A109.0
C13—C2—C1121.5 (2)C13—C14—H14A109.0
C13—C2—C3131.1 (2)C15—C14—H14B109.0
C1—C2—C3105.7 (2)C13—C14—H14B109.0
C5—C3—C4121.5 (2)H14A—C14—H14B107.8
C5—C3—C2133.1 (2)C13—C14—H14C109.5
C4—C3—C2104.8 (2)C13—C14—H14D109.5
C10—O4—C9107.47 (18)H14C—C14—H14D109.5
O1—C4—O2118.4 (3)C13—C14—H14E109.5
O1—C4—C3132.9 (3)H14C—C14—H14E109.5
O2—C4—C3108.6 (2)H14D—C14—H14E109.5
C3—C5—C7124.7 (2)C18—C14—H14F110.4
C3—C5—C6121.7 (2)C13—C14—H14F110.4
C7—C5—C6113.6 (2)C18—C14—H14G110.4
C5—C6—H6A109.5C13—C14—H14G110.4
C5—C6—H6B109.5H14F—C14—H14G108.6
H6A—C6—H6B109.5C17—C16—C13102.1 (6)
C5—C6—H6C109.5C13—C16—H16A109.5
H6A—C6—H6C109.5C13—C16—H16B109.5
H6B—C6—H6C109.5H16A—C16—H16B109.5
C10—C7—C8105.3 (2)C13—C16—H16C109.5
C10—C7—C5128.0 (2)H16A—C16—H16C109.5
C8—C7—C5126.3 (2)H16B—C16—H16C109.5
C7—C10—O4109.80 (19)C17—C16—H16D111.3
C7—C10—C11135.3 (2)C13—C16—H16D111.3
O4—C10—C11114.8 (2)C17—C16—H16E111.3
C8—C9—O4109.3 (2)C13—C16—H16E111.3
C8—C9—C12134.6 (2)H16D—C16—H16E109.2
O4—C9—C12116.1 (2)C14—C15—H15A109.5
C9—C8—C7108.1 (2)C14—C15—H15B109.5
C9—C8—H8125.9H15A—C15—H15B109.5
C7—C8—H8125.9C14—C15—H15C109.5
C10—C11—H11A109.5H15A—C15—H15C109.5
C10—C11—H11B109.5H15B—C15—H15C109.5
H11A—C11—H11B109.5C16—C17—H17A109.5
C10—C11—H11C109.5C16—C17—H17B109.5
H11A—C11—H11C109.5H17A—C17—H17B109.5
H11B—C11—H11C109.5C16—C17—H17C109.5
C9—C12—H12A109.5H17A—C17—H17C109.5
C9—C12—H12B109.5H17B—C17—H17C109.5
H12A—C12—H12B109.5C14—C18—H18A109.5
C9—C12—H12C109.5C14—C18—H18B109.5
H12A—C12—H12C109.5H18A—C18—H18B109.5
H12B—C12—H12C109.5C14—C18—H18C109.5
C2—C13—C16122.6 (2)H18A—C18—H18C109.5
C2—C13—C14122.8 (2)H18B—C18—H18C109.5
O3—C1—O2—C4176.7 (2)C6—C5—C7—C832.6 (3)
C2—C1—O2—C44.8 (3)C8—C7—C10—O40.7 (3)
O3—C1—C2—C1324.3 (4)C5—C7—C10—O4173.3 (2)
O2—C1—C2—C13153.9 (2)C8—C7—C10—C11174.3 (3)
O3—C1—C2—C3169.0 (3)C5—C7—C10—C111.7 (5)
O2—C1—C2—C312.7 (3)C9—O4—C10—C70.1 (3)
C13—C2—C3—C539.6 (5)C9—O4—C10—C11176.1 (2)
C1—C2—C3—C5155.5 (3)C10—O4—C9—C80.6 (3)
C13—C2—C3—C4149.5 (3)C10—O4—C9—C12179.6 (2)
C1—C2—C3—C415.3 (3)O4—C9—C8—C71.0 (3)
C1—O2—C4—O1176.2 (3)C12—C9—C8—C7179.8 (3)
C1—O2—C4—C35.3 (3)C10—C7—C8—C91.1 (3)
C5—C3—C4—O119.1 (5)C5—C7—C8—C9173.8 (2)
C2—C3—C4—O1168.8 (3)C1—C2—C13—C16165.7 (3)
C5—C3—C4—O2159.2 (2)C3—C2—C13—C162.9 (4)
C2—C3—C4—O213.0 (3)C1—C2—C13—C1412.9 (4)
C4—C3—C5—C7159.8 (2)C3—C2—C13—C14175.8 (3)
C2—C3—C5—C79.7 (4)C2—C13—C14—C18166.8 (10)
C4—C3—C5—C618.4 (4)C16—C13—C14—C1814.4 (10)
C2—C3—C5—C6172.1 (3)C2—C13—C14—C1582.2 (4)
C3—C5—C7—C1039.8 (4)C16—C13—C14—C1599.1 (3)
C6—C5—C7—C10138.6 (3)C2—C13—C16—C17169.6 (7)
C3—C5—C7—C8149.1 (3)C14—C13—C16—C179.1 (7)
(3E) 3-furylfulgide with cyclopentylidene-3E top
Crystal data top
C17H18O4F(000) = 608
Mr = 286.31Dx = 1.299 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71075 Å
a = 12.3175 (7) ÅCell parameters from 11394 reflections
b = 8.1863 (4) Åθ = 3.0–27.4°
c = 15.1293 (8) ŵ = 0.09 mm1
β = 106.327 (1)°T = 173 K
V = 1464.04 (13) Å3Rods, yellow
Z = 40.29 × 0.19 × 0.11 mm
Data collection top
Rigaku RAXIS-RAPID Imaging Plate
diffractometer
2764 reflections with I > 2σ(I)
Oscillation Photograph scansRint = 0.027
Absorption correction: multi scan
ABSCOR (Higashi, 1995)
θmax = 27.4°, θmin = 3.0°
Tmin = 0.860, Tmax = 0.968h = 1415
13814 measured reflectionsk = 1010
3340 independent reflectionsl = 1919
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)] = 0.045Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.127H-atom parameters constrained
S = 1.08 w = 1/[σ2(Fo2) + (0.0782P)2 + 0.1612P]
where P = (Fo2 + 2Fc2)/3
3340 reflections(Δ/σ)max < 0.001
193 parametersΔρmax = 0.35 e Å3
0 restraintsΔρmin = 0.18 e Å3
Crystal data top
C17H18O4V = 1464.04 (13) Å3
Mr = 286.31Z = 4
Monoclinic, P21/nMo Kα radiation
a = 12.3175 (7) ŵ = 0.09 mm1
b = 8.1863 (4) ÅT = 173 K
c = 15.1293 (8) Å0.29 × 0.19 × 0.11 mm
β = 106.327 (1)°
Data collection top
Rigaku RAXIS-RAPID Imaging Plate
diffractometer
3340 independent reflections
Absorption correction: multi scan
ABSCOR (Higashi, 1995)
2764 reflections with I > 2σ(I)
Tmin = 0.860, Tmax = 0.968Rint = 0.027
13814 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0450 restraints
wR(F2) = 0.127H-atom parameters constrained
S = 1.08Δρmax = 0.35 e Å3
3340 reflectionsΔρmin = 0.18 e Å3
193 parameters
Special details top

Experimental. 3-furylfulgide with cyclopentylidene-3E

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. 3-furylfulgide with cyclopentylidene-3E

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O10.17754 (10)0.3614 (2)0.07081 (7)0.0641 (4)
O20.35993 (8)0.34821 (13)0.06750 (6)0.0395 (3)
O30.54775 (9)0.31349 (14)0.02929 (6)0.0410 (3)
O40.42652 (7)0.40079 (12)0.37465 (6)0.0317 (2)
C10.27252 (12)0.3355 (2)0.02548 (9)0.0397 (3)
C20.32283 (10)0.29451 (16)0.07301 (8)0.0293 (3)
C30.44113 (10)0.25109 (15)0.08094 (7)0.0265 (3)
C40.46269 (11)0.30594 (16)0.00575 (8)0.0317 (3)
C50.51535 (10)0.15205 (15)0.13956 (8)0.0260 (3)
C60.63082 (10)0.10485 (17)0.13030 (8)0.0323 (3)
H6A0.67850.20290.13240.039*
H6B0.62350.04650.07160.039*
C70.68212 (11)0.00743 (18)0.21294 (9)0.0363 (3)
H7A0.72930.09360.19640.044*
H7B0.72910.05570.26570.044*
C80.57941 (11)0.08147 (16)0.23591 (9)0.0336 (3)
H8A0.59910.11820.30080.040*
H8B0.54900.17530.19520.040*
C90.49383 (10)0.06003 (16)0.21902 (8)0.0282 (3)
H9A0.41530.01820.20300.034*
H9B0.50700.13060.27420.034*
C100.26377 (10)0.31375 (16)0.13661 (8)0.0292 (3)
C110.13623 (11)0.3329 (2)0.10719 (10)0.0401 (3)
H11A0.11670.44750.11360.060*
H11B0.10340.26450.14620.060*
H11C0.10620.29930.04280.060*
C120.31553 (10)0.32528 (15)0.23606 (8)0.0270 (3)
C130.26423 (11)0.27481 (17)0.30698 (9)0.0320 (3)
H130.19410.21940.29760.038*
C140.33400 (11)0.32072 (18)0.38825 (9)0.0343 (3)
C150.33068 (14)0.3057 (3)0.48586 (10)0.0538 (5)
H15A0.25670.26360.48720.081*
H15B0.34310.41320.51550.081*
H15C0.39010.23030.51900.081*
C160.50322 (11)0.49045 (17)0.25283 (9)0.0355 (3)
H16A0.56480.41480.25260.053*
H16B0.53260.57980.29600.053*
H16C0.47140.53510.19080.053*
C170.41391 (10)0.40237 (15)0.28159 (8)0.0276 (3)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0412 (6)0.1118 (12)0.0321 (5)0.0099 (6)0.0015 (4)0.0151 (6)
O20.0444 (6)0.0524 (6)0.0213 (4)0.0011 (4)0.0088 (4)0.0049 (4)
O30.0458 (6)0.0523 (6)0.0309 (5)0.0026 (4)0.0209 (4)0.0039 (4)
O40.0300 (5)0.0421 (5)0.0249 (4)0.0027 (4)0.0106 (3)0.0043 (4)
C10.0391 (7)0.0528 (9)0.0253 (6)0.0006 (6)0.0061 (5)0.0034 (6)
C20.0280 (6)0.0354 (7)0.0228 (5)0.0020 (5)0.0044 (4)0.0010 (5)
C30.0298 (6)0.0305 (6)0.0206 (5)0.0051 (5)0.0094 (4)0.0025 (5)
C40.0405 (7)0.0339 (6)0.0218 (5)0.0032 (5)0.0107 (5)0.0010 (5)
C50.0277 (6)0.0297 (6)0.0215 (5)0.0052 (4)0.0084 (4)0.0049 (4)
C60.0298 (6)0.0399 (7)0.0297 (6)0.0014 (5)0.0128 (5)0.0038 (5)
C70.0316 (6)0.0455 (8)0.0312 (6)0.0055 (5)0.0077 (5)0.0042 (6)
C80.0403 (7)0.0317 (7)0.0288 (6)0.0027 (5)0.0097 (5)0.0007 (5)
C90.0288 (6)0.0321 (6)0.0246 (5)0.0016 (5)0.0092 (4)0.0015 (5)
C100.0262 (6)0.0332 (6)0.0275 (6)0.0023 (5)0.0065 (4)0.0004 (5)
C110.0262 (6)0.0564 (9)0.0364 (7)0.0004 (6)0.0066 (5)0.0013 (6)
C120.0250 (6)0.0303 (6)0.0275 (6)0.0013 (4)0.0102 (4)0.0000 (5)
C130.0260 (6)0.0402 (7)0.0330 (6)0.0006 (5)0.0133 (5)0.0009 (5)
C140.0292 (6)0.0471 (8)0.0305 (6)0.0009 (5)0.0147 (5)0.0009 (5)
C150.0434 (9)0.0924 (14)0.0307 (7)0.0052 (8)0.0187 (6)0.0003 (8)
C160.0362 (7)0.0381 (7)0.0342 (6)0.0113 (5)0.0131 (5)0.0049 (5)
C170.0293 (6)0.0306 (6)0.0245 (5)0.0001 (5)0.0100 (4)0.0016 (5)
Geometric parameters (Å, º) top
O1—C11.1970 (18)C8—H8B0.9900
O2—C41.3891 (16)C9—H9A0.9900
O2—C11.3995 (17)C9—H9B0.9900
O3—C41.1993 (16)C10—C121.4629 (16)
O4—C171.3724 (14)C10—C111.5158 (17)
O4—C141.3793 (16)C11—H11A0.9800
C1—C21.4826 (17)C11—H11B0.9800
C2—C101.3687 (17)C11—H11C0.9800
C2—C31.4717 (17)C12—C171.3681 (17)
C3—C51.3505 (17)C12—C131.4500 (16)
C3—C41.4793 (15)C13—C141.3407 (19)
C5—C91.5040 (16)C13—H130.9500
C5—C61.5178 (17)C14—C151.4939 (18)
C6—C71.5372 (19)C15—H15A0.9800
C6—H6A0.9900C15—H15B0.9800
C6—H6B0.9900C15—H15C0.9800
C7—C81.5283 (19)C16—C171.4794 (17)
C7—H7A0.9900C16—H16A0.9800
C7—H7B0.9900C16—H16B0.9800
C8—C91.5385 (18)C16—H16C0.9800
C8—H8A0.9900
C4—O2—C1110.36 (9)C8—C9—H9A110.9
C17—O4—C14107.31 (9)C5—C9—H9B110.9
O1—C1—O2118.65 (12)C8—C9—H9B110.9
O1—C1—C2132.92 (14)H9A—C9—H9B109.0
O2—C1—C2108.41 (11)C2—C10—C12124.50 (11)
C10—C2—C3132.86 (11)C2—C10—C11121.16 (11)
C10—C2—C1121.73 (12)C12—C10—C11114.29 (11)
C3—C2—C1105.14 (10)C10—C11—H11A109.5
C5—C3—C2132.11 (11)C10—C11—H11B109.5
C5—C3—C4120.49 (11)H11A—C11—H11B109.5
C2—C3—C4105.95 (10)C10—C11—H11C109.5
O3—C4—O2119.63 (11)H11A—C11—H11C109.5
O3—C4—C3131.95 (12)H11B—C11—H11C109.5
O2—C4—C3108.37 (10)C17—C12—C13105.52 (10)
C3—C5—C9125.93 (11)C17—C12—C10128.01 (11)
C3—C5—C6124.83 (10)C13—C12—C10126.02 (11)
C9—C5—C6109.06 (10)C14—C13—C12107.36 (11)
C5—C6—C7104.99 (10)C14—C13—H13126.3
C5—C6—H6A110.7C12—C13—H13126.3
C7—C6—H6A110.7C13—C14—O4109.87 (11)
C5—C6—H6B110.7C13—C14—C15134.01 (13)
C7—C6—H6B110.7O4—C14—C15116.11 (12)
H6A—C6—H6B108.8C14—C15—H15A109.5
C8—C7—C6104.17 (10)C14—C15—H15B109.5
C8—C7—H7A110.9H15A—C15—H15B109.5
C6—C7—H7A110.9C14—C15—H15C109.5
C8—C7—H7B110.9H15A—C15—H15C109.5
C6—C7—H7B110.9H15B—C15—H15C109.5
H7A—C7—H7B108.9C17—C16—H16A109.5
C7—C8—C9103.65 (10)C17—C16—H16B109.5
C7—C8—H8A111.0H16A—C16—H16B109.5
C9—C8—H8A111.0C17—C16—H16C109.5
C7—C8—H8B111.0H16A—C16—H16C109.5
C9—C8—H8B111.0H16B—C16—H16C109.5
H8A—C8—H8B109.0C12—C17—O4109.93 (10)
C5—C9—C8104.09 (10)C12—C17—C16134.70 (11)
C5—C9—H9A110.9O4—C17—C16115.29 (10)
C4—O2—C1—O1176.97 (15)C3—C5—C9—C8157.19 (12)
C4—O2—C1—C24.72 (16)C6—C5—C9—C817.99 (13)
O1—C1—C2—C1014.6 (3)C7—C8—C9—C534.04 (12)
O2—C1—C2—C10163.41 (12)C3—C2—C10—C1212.9 (2)
O1—C1—C2—C3170.66 (19)C1—C2—C10—C12160.20 (13)
O2—C1—C2—C311.36 (15)C3—C2—C10—C11170.02 (13)
C10—C2—C3—C533.5 (2)C1—C2—C10—C1116.9 (2)
C1—C2—C3—C5152.53 (13)C2—C10—C12—C1737.9 (2)
C10—C2—C3—C4160.61 (14)C11—C10—C12—C17139.35 (14)
C1—C2—C3—C413.32 (14)C2—C10—C12—C13150.94 (13)
C1—O2—C4—O3178.23 (13)C11—C10—C12—C1331.81 (18)
C1—O2—C4—C33.96 (15)C17—C12—C13—C141.10 (15)
C5—C3—C4—O320.6 (2)C10—C12—C13—C14173.88 (13)
C2—C3—C4—O3171.56 (14)C12—C13—C14—O41.16 (15)
C5—C3—C4—O2156.84 (11)C12—C13—C14—C15179.96 (17)
C2—C3—C4—O211.01 (13)C17—O4—C14—C130.78 (15)
C2—C3—C5—C92.5 (2)C17—O4—C14—C15179.82 (13)
C4—C3—C5—C9166.64 (11)C13—C12—C17—O40.63 (14)
C2—C3—C5—C6171.98 (12)C10—C12—C17—O4173.22 (11)
C4—C3—C5—C67.81 (18)C13—C12—C17—C16175.92 (14)
C3—C5—C6—C7179.76 (11)C10—C12—C17—C163.3 (2)
C9—C5—C6—C74.99 (13)C14—O4—C17—C120.05 (14)
C5—C6—C7—C826.19 (13)C14—O4—C17—C16177.34 (11)
C6—C7—C8—C937.36 (12)
(4E) 3-furylfulgide with cyclohexylidene-4E top
Crystal data top
C18H20O4F(000) = 640
Mr = 300.34Dx = 1.262 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71075 Å
a = 9.6047 (7) ÅCell parameters from 8916 reflections
b = 14.4631 (10) Åθ = 3.1–27.4°
c = 11.3814 (8) ŵ = 0.09 mm1
β = 91.355 (2)°T = 173 K
V = 1580.59 (19) Å3Plates, white
Z = 40.31 × 0.17 × 0.07 mm
Data collection top
Rigaku RAXIS-RAPID Imaging Plate
diffractometer
1915 reflections with I > 2σ(I)
Oscillation Photograph scansRint = 0.047
Absorption correction: multi-scan
ABSCOR (Higashi, 1995)
θmax = 27.4°, θmin = 3.1°
Tmin = 0.872, Tmax = 0.894h = 1212
15155 measured reflectionsk = 1818
3582 independent reflectionsl = 1414
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)] = 0.042Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.130H-atom parameters constrained
S = 1.04 w = 1/[σ2(Fo2) + (0.0606P)2 + 0.064P]
where P = (Fo2 + 2Fc2)/3
3582 reflections(Δ/σ)max < 0.001
202 parametersΔρmax = 0.18 e Å3
0 restraintsΔρmin = 0.18 e Å3
Crystal data top
C18H20O4V = 1580.59 (19) Å3
Mr = 300.34Z = 4
Monoclinic, P21/nMo Kα radiation
a = 9.6047 (7) ŵ = 0.09 mm1
b = 14.4631 (10) ÅT = 173 K
c = 11.3814 (8) Å0.31 × 0.17 × 0.07 mm
β = 91.355 (2)°
Data collection top
Rigaku RAXIS-RAPID Imaging Plate
diffractometer
3582 independent reflections
Absorption correction: multi-scan
ABSCOR (Higashi, 1995)
1915 reflections with I > 2σ(I)
Tmin = 0.872, Tmax = 0.894Rint = 0.047
15155 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0420 restraints
wR(F2) = 0.130H-atom parameters constrained
S = 1.04Δρmax = 0.18 e Å3
3582 reflectionsΔρmin = 0.18 e Å3
202 parameters
Special details top

Experimental. 3-furylfulgide with cyclohexylidene-4E

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. 3-furylfulgide with cyclohexylidene-4E

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O10.07867 (15)0.91017 (10)0.34554 (11)0.0724 (4)
O20.02297 (17)0.78884 (12)0.26017 (12)0.0878 (5)
O30.17927 (17)1.00915 (10)0.46856 (14)0.0867 (5)
O40.08630 (12)0.68720 (8)0.80884 (9)0.0547 (3)
C10.0387 (2)0.81726 (16)0.34344 (16)0.0622 (5)
C20.09090 (17)0.77254 (12)0.45014 (14)0.0495 (4)
C30.12909 (17)0.84941 (12)0.52834 (14)0.0489 (4)
C40.1382 (2)0.93195 (15)0.45264 (17)0.0622 (5)
C50.13068 (17)0.85484 (11)0.64775 (15)0.0495 (4)
C60.1895 (2)0.93696 (13)0.71089 (17)0.0698 (6)
H6A0.11420.96970.75300.105*
H6B0.25840.91590.76710.105*
H6C0.23430.97870.65370.105*
C70.06896 (17)0.78333 (11)0.72474 (14)0.0472 (4)
C80.05817 (18)0.74326 (12)0.71333 (14)0.0487 (4)
C90.17005 (19)0.75015 (14)0.62634 (16)0.0607 (5)
H9A0.16130.69900.57010.091*
H9B0.26100.74690.66700.091*
H9C0.16180.80910.58430.091*
C100.12098 (19)0.75029 (13)0.83461 (15)0.0551 (5)
H100.20730.76670.86790.066*
C110.02661 (19)0.69245 (13)0.88156 (14)0.0543 (4)
C120.0147 (2)0.63655 (16)0.99144 (17)0.0762 (6)
H12A0.04250.66991.04990.114*
H12B0.02890.57700.97420.114*
H12C0.10770.62601.02240.114*
C130.12334 (18)0.68165 (13)0.45707 (14)0.0523 (4)
C140.2131 (2)0.64378 (13)0.55156 (15)0.0590 (5)
H14A0.25290.69560.59670.071*
H14B0.15540.60590.60640.071*
C150.3317 (2)0.58429 (14)0.49970 (18)0.0689 (6)
H15A0.38560.55730.56440.083*
H15B0.39540.62380.45190.083*
C160.2764 (3)0.50747 (14)0.4238 (2)0.0839 (7)
H16A0.21700.46580.47240.101*
H16B0.35520.47080.39090.101*
C170.1928 (3)0.54651 (16)0.32525 (19)0.0859 (7)
H17A0.25540.58180.27140.103*
H17B0.15220.49500.28010.103*
C180.0752 (2)0.61012 (15)0.37018 (17)0.0725 (6)
H18A0.00140.57190.40800.087*
H18B0.03410.64210.30240.087*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0685 (9)0.0853 (10)0.0629 (8)0.0112 (8)0.0077 (7)0.0252 (7)
O20.0784 (10)0.1305 (14)0.0551 (8)0.0160 (10)0.0132 (7)0.0013 (8)
O30.0918 (12)0.0604 (9)0.1071 (11)0.0091 (8)0.0149 (9)0.0195 (8)
O40.0490 (7)0.0611 (7)0.0537 (7)0.0021 (6)0.0027 (6)0.0060 (6)
C10.0494 (11)0.0877 (15)0.0492 (11)0.0106 (10)0.0078 (9)0.0052 (10)
C20.0408 (9)0.0636 (11)0.0437 (9)0.0014 (8)0.0060 (7)0.0010 (8)
C30.0406 (9)0.0528 (10)0.0531 (9)0.0002 (8)0.0047 (7)0.0064 (8)
C40.0520 (11)0.0639 (13)0.0700 (12)0.0042 (10)0.0143 (9)0.0122 (10)
C50.0422 (9)0.0491 (9)0.0571 (10)0.0011 (8)0.0016 (8)0.0030 (8)
C60.0757 (14)0.0612 (12)0.0726 (12)0.0102 (10)0.0045 (11)0.0090 (10)
C70.0437 (9)0.0514 (9)0.0463 (9)0.0022 (8)0.0031 (7)0.0035 (7)
C80.0468 (10)0.0532 (10)0.0458 (9)0.0018 (8)0.0042 (7)0.0006 (7)
C90.0473 (10)0.0758 (13)0.0591 (11)0.0048 (9)0.0032 (9)0.0049 (9)
C100.0446 (10)0.0693 (12)0.0514 (9)0.0006 (9)0.0019 (8)0.0013 (8)
C110.0490 (10)0.0642 (11)0.0497 (9)0.0055 (9)0.0002 (8)0.0023 (8)
C120.0683 (14)0.0907 (16)0.0695 (12)0.0004 (12)0.0023 (10)0.0244 (11)
C130.0496 (10)0.0606 (11)0.0462 (9)0.0031 (9)0.0097 (8)0.0039 (8)
C140.0672 (12)0.0554 (11)0.0541 (10)0.0048 (9)0.0063 (9)0.0010 (8)
C150.0706 (14)0.0610 (12)0.0746 (12)0.0107 (10)0.0122 (10)0.0066 (10)
C160.1003 (18)0.0614 (13)0.0884 (15)0.0061 (12)0.0312 (14)0.0047 (12)
C170.1041 (19)0.0776 (15)0.0748 (14)0.0061 (14)0.0209 (13)0.0245 (12)
C180.0769 (15)0.0754 (13)0.0650 (12)0.0109 (11)0.0039 (10)0.0160 (11)
Geometric parameters (Å, º) top
O1—C41.395 (2)C10—C111.336 (3)
O1—C11.398 (3)C10—H100.9500
O2—C11.202 (2)C11—C121.491 (2)
O3—C41.199 (2)C12—H12A0.9800
O4—C81.3777 (19)C12—H12B0.9800
O4—C111.382 (2)C12—H12C0.9800
C1—C21.474 (2)C13—C141.498 (2)
C2—C131.354 (2)C13—C181.511 (2)
C2—C31.476 (2)C14—C151.534 (3)
C3—C51.362 (2)C14—H14A0.9900
C3—C41.474 (3)C14—H14B0.9900
C5—C71.471 (2)C15—C161.511 (3)
C5—C61.505 (2)C15—H15A0.9900
C6—H6A0.9800C15—H15B0.9900
C6—H6B0.9800C16—C171.505 (3)
C6—H6C0.9800C16—H16A0.9900
C7—C81.361 (2)C16—H16B0.9900
C7—C101.439 (2)C17—C181.535 (3)
C8—C91.482 (2)C17—H17A0.9900
C9—H9A0.9800C17—H17B0.9900
C9—H9B0.9800C18—H18A0.9900
C9—H9C0.9800C18—H18B0.9900
C4—O1—C1110.53 (14)O4—C11—C12115.26 (16)
C8—O4—C11107.35 (13)C11—C12—H12A109.5
O2—C1—O1118.88 (18)C11—C12—H12B109.5
O2—C1—C2133.1 (2)H12A—C12—H12B109.5
O1—C1—C2107.97 (16)C11—C12—H12C109.5
C13—C2—C1123.86 (16)H12A—C12—H12C109.5
C13—C2—C3129.47 (15)H12B—C12—H12C109.5
C1—C2—C3105.10 (16)C2—C13—C14122.28 (16)
C5—C3—C4122.34 (16)C2—C13—C18123.53 (17)
C5—C3—C2130.84 (15)C14—C13—C18114.18 (16)
C4—C3—C2105.66 (15)C13—C14—C15111.31 (14)
O3—C4—O1119.04 (18)C13—C14—H14A109.4
O3—C4—C3132.9 (2)C15—C14—H14A109.4
O1—C4—C3107.95 (17)C13—C14—H14B109.4
C3—C5—C7122.69 (15)C15—C14—H14B109.4
C3—C5—C6122.35 (16)H14A—C14—H14B108.0
C7—C5—C6114.89 (15)C16—C15—C14111.38 (18)
C5—C6—H6A109.5C16—C15—H15A109.4
C5—C6—H6B109.5C14—C15—H15A109.4
H6A—C6—H6B109.5C16—C15—H15B109.4
C5—C6—H6C109.5C14—C15—H15B109.4
H6A—C6—H6C109.5H15A—C15—H15B108.0
H6B—C6—H6C109.5C17—C16—C15110.55 (17)
C8—C7—C10105.79 (15)C17—C16—H16A109.5
C8—C7—C5126.34 (16)C15—C16—H16A109.5
C10—C7—C5127.42 (16)C17—C16—H16B109.5
C7—C8—O4109.58 (14)C15—C16—H16B109.5
C7—C8—C9134.57 (16)H16A—C16—H16B108.1
O4—C8—C9115.78 (14)C16—C17—C18112.20 (17)
C8—C9—H9A109.5C16—C17—H17A109.2
C8—C9—H9B109.5C18—C17—H17A109.2
H9A—C9—H9B109.5C16—C17—H17B109.2
C8—C9—H9C109.5C18—C17—H17B109.2
H9A—C9—H9C109.5H17A—C17—H17B107.9
H9B—C9—H9C109.5C13—C18—C17113.23 (18)
C11—C10—C7108.02 (16)C13—C18—H18A108.9
C11—C10—H10126.0C17—C18—H18A108.9
C7—C10—H10126.0C13—C18—H18B108.9
C10—C11—O4109.24 (15)C17—C18—H18B108.9
C10—C11—C12135.47 (18)H18A—C18—H18B107.7
C4—O1—C1—O2175.07 (17)C10—C7—C8—O40.56 (19)
C4—O1—C1—C27.3 (2)C5—C7—C8—O4173.34 (15)
O2—C1—C2—C1325.2 (3)C10—C7—C8—C9176.35 (19)
O1—C1—C2—C13151.91 (17)C5—C7—C8—C93.6 (3)
O2—C1—C2—C3167.9 (2)C11—O4—C8—C70.10 (18)
O1—C1—C2—C314.98 (18)C11—O4—C8—C9177.66 (15)
C13—C2—C3—C543.2 (3)C8—C7—C10—C111.0 (2)
C1—C2—C3—C5150.96 (18)C5—C7—C10—C11173.72 (16)
C13—C2—C3—C4149.22 (18)C7—C10—C11—O41.1 (2)
C1—C2—C3—C416.65 (18)C7—C10—C11—C12179.3 (2)
C1—O1—C4—O3179.44 (18)C8—O4—C11—C100.78 (19)
C1—O1—C4—C33.5 (2)C8—O4—C11—C12179.38 (16)
C5—C3—C4—O320.3 (3)C1—C2—C13—C14161.83 (17)
C2—C3—C4—O3170.7 (2)C3—C2—C13—C141.7 (3)
C5—C3—C4—O1156.12 (16)C1—C2—C13—C1817.0 (3)
C2—C3—C4—O112.80 (18)C3—C2—C13—C18179.45 (17)
C4—C3—C5—C7155.36 (17)C2—C13—C14—C15129.21 (18)
C2—C3—C5—C710.5 (3)C18—C13—C14—C1549.8 (2)
C4—C3—C5—C621.5 (3)C13—C14—C15—C1655.6 (2)
C2—C3—C5—C6172.65 (17)C14—C15—C16—C1758.5 (2)
C3—C5—C7—C846.0 (3)C15—C16—C17—C1854.9 (3)
C6—C5—C7—C8131.09 (19)C2—C13—C18—C17132.1 (2)
C3—C5—C7—C10142.76 (18)C14—C13—C18—C1746.9 (2)
C6—C5—C7—C1040.1 (2)C16—C17—C18—C1349.1 (3)

Experimental details

(1E)(2E)(3E)(4E)
Crystal data
Chemical formulaC15H16O4C16H18O4C17H18O4C18H20O4
Mr260.28274.30286.31300.34
Crystal system, space groupMonoclinic, P21/nMonoclinic, P21/nMonoclinic, P21/nMonoclinic, P21/n
Temperature (K)173173173173
a, b, c (Å)12.560 (7), 7.667 (5), 14.624 (9)12.6826 (9), 7.9499 (6), 14.9392 (11)12.3175 (7), 8.1863 (4), 15.1293 (8)9.6047 (7), 14.4631 (10), 11.3814 (8)
β (°) 109.259 (16) 107.531 (2) 106.327 (1) 91.355 (2)
V3)1329.5 (15)1436.29 (18)1464.04 (13)1580.59 (19)
Z4444
Radiation typeMo KαMo KαMo KαMo Kα
µ (mm1)0.090.090.090.09
Crystal size (mm)0.18 × 0.10 × 0.100.13 × 0.09 × 0.030.29 × 0.19 × 0.110.31 × 0.17 × 0.07
Data collection
DiffractometerRigaku RAXIS-RAPID Imaging Plate
diffractometer
Rigaku RAXIS-RAPID Imaging Plate
diffractometer
Rigaku RAXIS-RAPID Imaging Plate
diffractometer
Rigaku RAXIS-RAPID Imaging Plate
diffractometer
Absorption correctionMulti-scan
ABSCOR (Higashi, 1995)
Multi-scan
ABSCOR (Higashi, 1995)
Multi scan
ABSCOR (Higashi, 1995)
Multi-scan
ABSCOR (Higashi, 1995)
Tmin, Tmax0.814, 0.9420.886, 0.9460.860, 0.9680.872, 0.894
No. of measured, independent and
observed [I > 2σ(I)] reflections
12492, 3032, 2258 13610, 3305, 1772 13814, 3340, 2764 15155, 3582, 1915
Rint0.0230.0520.0270.047
(sin θ/λ)max1)0.6490.6490.6480.647
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.048, 0.141, 1.08 0.061, 0.207, 1.01 0.045, 0.127, 1.08 0.042, 0.130, 1.04
No. of reflections3032330533403582
No. of parameters177201193202
No. of restraints1100
H-atom treatmentH-atom parameters constrainedH-atom parameters constrainedH-atom parameters constrainedH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.34, 0.240.24, 0.240.35, 0.180.18, 0.18

Computer programs: PROCESS-AUTO (Rigaku, 1998), PROCESS-AUTO, TEXSAN (Rigaku, 1999), SHELXS97 (Sheldrick, 2008), SHELXS97 (Sheldrick, 1990), SHELXL97 (Sheldrick, 2008), SHELXL2013 (Sheldrick, 2013), SHELXL97.

 

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