Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S2052520615015267/gw5039sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S2052520615015267/gw50391Esup2.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S2052520615015267/gw50392Esup3.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S2052520615015267/gw50393Esup4.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S2052520615015267/gw50394Esup5.hkl | |
Portable Document Format (PDF) file https://doi.org/10.1107/S2052520615015267/gw5039sup6.pdf |
CCDC references: 1010419; 1010420; 1010421; 1010422
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).
C15H16O4 | F(000) = 552 |
Mr = 260.28 | Dx = 1.300 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71075 Å |
a = 12.560 (7) Å | Cell parameters from 2346 reflections |
b = 7.667 (5) Å | θ = 3.0–27.6° |
c = 14.624 (9) Å | µ = 0.09 mm−1 |
β = 109.259 (16)° | T = 173 K |
V = 1329.5 (15) Å3 | Diamond, orange |
Z = 4 | 0.18 × 0.10 × 0.10 mm |
Rigaku RAXIS-RAPID Imaging Plate diffractometer | 2258 reflections with I > 2σ(I) |
Oscillation Photograph scans | Rint = 0.023 |
Absorption correction: multi-scan ABSCOR (Higashi, 1995) | θmax = 27.5°, θmin = 3.0° |
Tmin = 0.814, Tmax = 0.942 | h = −16→16 |
12492 measured reflections | k = −9→9 |
3032 independent reflections | l = −18→18 |
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)] = 0.048 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.141 | H-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 parameters | Δρmax = 0.34 e Å−3 |
1 restraint | Δρmin = −0.24 e Å−3 |
C15H16O4 | V = 1329.5 (15) Å3 |
Mr = 260.28 | Z = 4 |
Monoclinic, P21/n | Mo Kα radiation |
a = 12.560 (7) Å | µ = 0.09 mm−1 |
b = 7.667 (5) Å | T = 173 K |
c = 14.624 (9) Å | 0.18 × 0.10 × 0.10 mm |
β = 109.259 (16)° |
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 = 0.942 | Rint = 0.023 |
12492 measured reflections |
R[F2 > 2σ(F2)] = 0.048 | 1 restraint |
wR(F2) = 0.141 | H-atom parameters constrained |
S = 1.08 | Δρmax = 0.34 e Å−3 |
3032 reflections | Δρmin = −0.24 e Å−3 |
177 parameters |
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. |
x | y | z | Uiso*/Ueq | ||
C12 | 0.35124 (12) | 0.2992 (2) | 0.38698 (11) | 0.0352 (4) | |
O1 | 0.20753 (11) | 0.3115 (2) | −0.09531 (9) | 0.0607 (4) | |
O2 | 0.39117 (10) | 0.31867 (17) | −0.07495 (8) | 0.0452 (3) | |
O3 | 0.57910 (11) | 0.31103 (19) | −0.01869 (9) | 0.0517 (4) | |
O4 | 0.44208 (8) | 0.38865 (14) | 0.37705 (7) | 0.0325 (3) | |
C1 | 0.30152 (15) | 0.2946 (2) | −0.04044 (11) | 0.0416 (4) | |
C2 | 0.34760 (13) | 0.2559 (2) | 0.06423 (10) | 0.0325 (3) | |
C3 | 0.46785 (13) | 0.21904 (19) | 0.08324 (10) | 0.0323 (3) | |
C4 | 0.49306 (15) | 0.2866 (2) | −0.00229 (12) | 0.0389 (4) | |
C5 | 0.54002 (13) | 0.1160 (2) | 0.14982 (11) | 0.0347 (3) | |
C6 | 0.66243 (14) | 0.0989 (3) | 0.15835 (14) | 0.0495 (5) | |
H6A | 0.6688 | 0.0895 | 0.0935 | 0.074* | |
H6B | 0.6942 | −0.0057 | 0.1959 | 0.074* | |
H6C | 0.7039 | 0.2020 | 0.1911 | 0.074* | |
C7 | 0.50383 (14) | 0.0090 (2) | 0.21955 (12) | 0.0405 (4) | |
H7A | 0.5291 | 0.0651 | 0.2833 | 0.061* | |
H7B | 0.5372 | −0.1076 | 0.2245 | 0.061* | |
H7C | 0.4214 | −0.0007 | 0.1966 | 0.061* | |
C8 | 0.28639 (12) | 0.28179 (19) | 0.12470 (10) | 0.0316 (3) | |
C9 | 0.15964 (13) | 0.3004 (2) | 0.08688 (12) | 0.0415 (4) | |
H9A | 0.1337 | 0.3046 | 0.0159 | 0.062* | |
H9B | 0.1378 | 0.4082 | 0.1121 | 0.062* | |
H9C | 0.1251 | 0.2004 | 0.1081 | 0.062* | |
C10 | 0.33577 (12) | 0.30032 (19) | 0.22981 (10) | 0.0295 (3) | |
C11 | 0.43111 (11) | 0.38823 (19) | 0.28075 (10) | 0.0286 (3) | |
C13 | 0.28431 (12) | 0.2456 (2) | 0.29990 (11) | 0.0346 (3) | |
H13 | 0.2156 | 0.1831 | 0.2867 | 0.042* | |
C14 | 0.51761 (12) | 0.4895 (2) | 0.25533 (11) | 0.0353 (3) | |
H14A | 0.5839 | 0.4159 | 0.2633 | 0.053* | |
H14B | 0.5395 | 0.5913 | 0.2980 | 0.053* | |
H14C | 0.4868 | 0.5283 | 0.1879 | 0.053* | |
C15 | 0.34712 (16) | 0.2848 (3) | 0.48690 (12) | 0.0500 (5) | |
H15A | 0.2757 | 0.2308 | 0.4851 | 0.075* | |
H15B | 0.3528 | 0.4014 | 0.5156 | 0.075* | |
H15C | 0.4101 | 0.2128 | 0.5260 | 0.075* |
U11 | U22 | U33 | U12 | U13 | U23 | |
C12 | 0.0292 (7) | 0.0429 (9) | 0.0366 (8) | −0.0034 (6) | 0.0148 (6) | −0.0014 (6) |
O1 | 0.0478 (7) | 0.0900 (11) | 0.0331 (6) | 0.0038 (7) | −0.0017 (6) | 0.0012 (6) |
O2 | 0.0518 (7) | 0.0536 (8) | 0.0302 (6) | −0.0018 (6) | 0.0134 (5) | 0.0016 (5) |
O3 | 0.0515 (7) | 0.0627 (9) | 0.0493 (7) | −0.0038 (6) | 0.0281 (6) | 0.0021 (6) |
O4 | 0.0313 (5) | 0.0387 (6) | 0.0282 (5) | −0.0051 (4) | 0.0109 (4) | −0.0038 (4) |
C1 | 0.0449 (9) | 0.0454 (10) | 0.0304 (8) | −0.0016 (7) | 0.0069 (7) | −0.0039 (7) |
C2 | 0.0340 (7) | 0.0319 (8) | 0.0275 (7) | −0.0042 (6) | 0.0047 (6) | −0.0024 (6) |
C3 | 0.0358 (7) | 0.0321 (7) | 0.0290 (7) | −0.0033 (6) | 0.0109 (6) | −0.0051 (6) |
C4 | 0.0457 (8) | 0.0383 (8) | 0.0344 (7) | −0.0037 (7) | 0.0155 (7) | −0.0057 (6) |
C5 | 0.0362 (8) | 0.0335 (8) | 0.0344 (7) | −0.0003 (6) | 0.0116 (6) | −0.0076 (6) |
C6 | 0.0377 (9) | 0.0587 (12) | 0.0522 (10) | 0.0085 (8) | 0.0150 (8) | −0.0052 (8) |
C7 | 0.0439 (8) | 0.0345 (8) | 0.0409 (8) | 0.0052 (7) | 0.0108 (7) | 0.0026 (7) |
C8 | 0.0296 (7) | 0.0302 (7) | 0.0315 (7) | −0.0033 (5) | 0.0056 (6) | −0.0025 (6) |
C9 | 0.0315 (8) | 0.0487 (10) | 0.0390 (8) | −0.0039 (7) | 0.0047 (7) | −0.0045 (7) |
C10 | 0.0279 (7) | 0.0282 (7) | 0.0322 (7) | 0.0003 (5) | 0.0094 (6) | −0.0010 (5) |
C11 | 0.0287 (7) | 0.0296 (7) | 0.0269 (6) | 0.0004 (5) | 0.0083 (5) | −0.0011 (5) |
C13 | 0.0287 (7) | 0.0379 (8) | 0.0387 (8) | −0.0049 (6) | 0.0131 (6) | −0.0018 (6) |
C14 | 0.0360 (8) | 0.0375 (8) | 0.0322 (7) | −0.0099 (6) | 0.0108 (6) | −0.0025 (6) |
C15 | 0.0461 (9) | 0.0728 (13) | 0.0371 (9) | −0.0122 (9) | 0.0217 (8) | −0.0048 (8) |
C12—C13 | 1.338 (2) | C7—H7A | 0.9800 |
C12—O4 | 1.3794 (18) | C7—H7B | 0.9800 |
C12—C15 | 1.483 (2) | C7—H7C | 0.9800 |
O1—C1 | 1.196 (2) | C8—C10 | 1.462 (2) |
O2—C4 | 1.389 (2) | C8—C9 | 1.510 (2) |
O2—C1 | 1.390 (2) | C9—H9A | 0.9800 |
O3—C4 | 1.197 (2) | C9—H9B | 0.9800 |
O4—C11 | 1.3690 (18) | C9—H9C | 0.9800 |
C1—C2 | 1.477 (2) | C10—C11 | 1.362 (2) |
C2—C8 | 1.364 (2) | C10—C13 | 1.443 (2) |
C2—C3 | 1.470 (2) | C11—C14 | 1.479 (2) |
C3—C5 | 1.346 (2) | C13—H13 | 0.9500 |
C3—C4 | 1.481 (2) | C14—H14A | 0.9800 |
C5—C7 | 1.491 (2) | C14—H14B | 0.9800 |
C5—C6 | 1.507 (2) | C14—H14C | 0.9800 |
C6—H6A | 0.9800 | C15—H15A | 0.9800 |
C6—H6B | 0.9800 | C15—H15B | 0.9800 |
C6—H6C | 0.9800 | C15—H15C | 0.9800 |
C13—C12—O4 | 109.52 (13) | H7B—C7—H7C | 109.5 |
C13—C12—C15 | 134.40 (15) | C2—C8—C10 | 124.14 (14) |
O4—C12—C15 | 116.08 (13) | C2—C8—C9 | 121.85 (14) |
C4—O2—C1 | 110.55 (13) | C10—C8—C9 | 113.98 (13) |
C11—O4—C12 | 107.53 (11) | C8—C9—H9A | 109.5 |
O1—C1—O2 | 118.74 (16) | C8—C9—H9B | 109.5 |
O1—C1—C2 | 132.84 (17) | H9A—C9—H9B | 109.5 |
O2—C1—C2 | 108.39 (14) | C8—C9—H9C | 109.5 |
C8—C2—C3 | 131.98 (14) | H9A—C9—H9C | 109.5 |
C8—C2—C1 | 122.04 (15) | H9B—C9—H9C | 109.5 |
C3—C2—C1 | 105.16 (13) | C11—C10—C13 | 105.93 (13) |
C5—C3—C2 | 130.86 (14) | C11—C10—C8 | 127.92 (13) |
C5—C3—C4 | 122.38 (15) | C13—C10—C8 | 125.77 (13) |
C2—C3—C4 | 105.40 (13) | C10—C11—O4 | 109.62 (12) |
O3—C4—O2 | 118.95 (16) | C10—C11—C14 | 135.12 (14) |
O3—C4—C3 | 133.07 (17) | O4—C11—C14 | 115.11 (12) |
O2—C4—C3 | 107.95 (14) | C12—C13—C10 | 107.40 (14) |
C3—C5—C7 | 122.20 (15) | C12—C13—H13 | 126.3 |
C3—C5—C6 | 122.41 (15) | C10—C13—H13 | 126.3 |
C7—C5—C6 | 115.38 (14) | C11—C14—H14A | 109.5 |
C5—C6—H6A | 109.5 | C11—C14—H14B | 109.5 |
C5—C6—H6B | 109.5 | H14A—C14—H14B | 109.5 |
H6A—C6—H6B | 109.5 | C11—C14—H14C | 109.5 |
C5—C6—H6C | 109.5 | H14A—C14—H14C | 109.5 |
H6A—C6—H6C | 109.5 | H14B—C14—H14C | 109.5 |
H6B—C6—H6C | 109.5 | C12—C15—H15A | 109.5 |
C5—C7—H7A | 109.5 | C12—C15—H15B | 109.5 |
C5—C7—H7B | 109.5 | H15A—C15—H15B | 109.5 |
H7A—C7—H7B | 109.5 | C12—C15—H15C | 109.5 |
C5—C7—H7C | 109.5 | H15A—C15—H15C | 109.5 |
H7A—C7—H7C | 109.5 | H15B—C15—H15C | 109.5 |
C13—C12—O4—C11 | −0.70 (17) | C2—C3—C5—C6 | −178.79 (15) |
C15—C12—O4—C11 | −179.92 (14) | C4—C3—C5—C6 | 16.6 (2) |
C4—O2—C1—O1 | −177.51 (16) | C3—C2—C8—C10 | 8.5 (3) |
C4—O2—C1—C2 | 4.22 (18) | C1—C2—C8—C10 | −159.55 (15) |
O1—C1—C2—C8 | −19.9 (3) | C3—C2—C8—C9 | −173.80 (16) |
O2—C1—C2—C8 | 158.01 (15) | C1—C2—C8—C9 | 18.2 (2) |
O1—C1—C2—C3 | 169.3 (2) | C2—C8—C10—C11 | 40.0 (2) |
O2—C1—C2—C3 | −12.78 (17) | C9—C8—C10—C11 | −137.88 (16) |
C8—C2—C3—C5 | 39.8 (3) | C2—C8—C10—C13 | −148.17 (16) |
C1—C2—C3—C5 | −150.70 (17) | C9—C8—C10—C13 | 33.9 (2) |
C8—C2—C3—C4 | −153.59 (17) | C13—C10—C11—O4 | 0.87 (16) |
C1—C2—C3—C4 | 15.89 (16) | C8—C10—C11—O4 | 173.97 (13) |
C1—O2—C4—O3 | −175.88 (16) | C13—C10—C11—C14 | −174.18 (16) |
C1—O2—C4—C3 | 6.14 (18) | C8—C10—C11—C14 | −1.1 (3) |
C5—C3—C4—O3 | −23.5 (3) | C12—O4—C11—C10 | −0.16 (16) |
C2—C3—C4—O3 | 168.50 (19) | C12—O4—C11—C14 | 175.99 (13) |
C5—C3—C4—O2 | 154.10 (15) | O4—C12—C13—C10 | 1.22 (18) |
C2—C3—C4—O2 | −13.92 (16) | C15—C12—C13—C10 | −179.76 (19) |
C2—C3—C5—C7 | 1.9 (3) | C11—C10—C13—C12 | −1.29 (17) |
C4—C3—C5—C7 | −162.72 (14) | C8—C10—C13—C12 | −174.58 (14) |
C16H18O4 | F(000) = 584 |
Mr = 274.30 | Dx = 1.269 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71075 Å |
a = 12.6826 (9) Å | Cell parameters from 9442 reflections |
b = 7.9499 (6) Å | θ = 3.1–30.5° |
c = 14.9392 (11) Å | µ = 0.09 mm−1 |
β = 107.531 (2)° | T = 173 K |
V = 1436.29 (18) Å3 | Rods, yellow |
Z = 4 | 0.13 × 0.09 × 0.03 mm |
Rigaku RAXIS-RAPID Imaging Plate diffractometer | 1772 reflections with I > 2σ(I) |
Oscillation Photograph scans | Rint = 0.052 |
Absorption correction: multi-scan ABSCOR (Higashi, 1995) | θmax = 27.5°, θmin = 3.1° |
Tmin = 0.886, Tmax = 0.946 | h = −15→16 |
13610 measured reflections | k = −10→10 |
3305 independent reflections | l = −19→19 |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.061 | H-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 reflections | Δρmax = 0.24 e Å−3 |
201 parameters | Δρmin = −0.24 e Å−3 |
1 restraint | Extinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.016 (5) |
C16H18O4 | V = 1436.29 (18) Å3 |
Mr = 274.30 | Z = 4 |
Monoclinic, P21/n | Mo Kα radiation |
a = 12.6826 (9) Å | µ = 0.09 mm−1 |
b = 7.9499 (6) Å | T = 173 K |
c = 14.9392 (11) Å | 0.13 × 0.09 × 0.03 mm |
β = 107.531 (2)° |
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 = 0.946 | Rint = 0.052 |
13610 measured reflections |
R[F2 > 2σ(F2)] = 0.061 | 1 restraint |
wR(F2) = 0.207 | H-atom parameters constrained |
S = 1.01 | Δρmax = 0.24 e Å−3 |
3305 reflections | Δρmin = −0.24 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. |
x | y | z | Uiso*/Ueq | Occ. (<1) | |
O1 | 0.18822 (17) | 0.3387 (4) | −0.08316 (15) | 0.0893 (8) | |
C1 | 0.4688 (2) | 0.2975 (3) | −0.00784 (17) | 0.0530 (6) | |
O2 | 0.36756 (15) | 0.3378 (2) | −0.07351 (12) | 0.0608 (5) | |
C2 | 0.4470 (2) | 0.2337 (3) | 0.07742 (17) | 0.0491 (6) | |
O3 | 0.55203 (16) | 0.3155 (2) | −0.02922 (13) | 0.0641 (5) | |
C3 | 0.3299 (2) | 0.2755 (3) | 0.06657 (17) | 0.0507 (6) | |
O4 | 0.42893 (13) | 0.3929 (2) | 0.37383 (11) | 0.0514 (5) | |
C4 | 0.2817 (2) | 0.3174 (4) | −0.03401 (19) | 0.0617 (7) | |
C5 | 0.2721 (2) | 0.2995 (3) | 0.12939 (18) | 0.0496 (6) | |
C6 | 0.1475 (2) | 0.3200 (4) | 0.0978 (2) | 0.0617 (7) | |
H6A | 0.1193 | 0.3067 | 0.0295 | 0.093* | |
H6B | 0.1284 | 0.4322 | 0.1152 | 0.093* | |
H6C | 0.1144 | 0.2344 | 0.1281 | 0.093* | |
C7 | 0.32192 (18) | 0.3129 (3) | 0.23120 (16) | 0.0463 (6) | |
C10 | 0.41742 (18) | 0.3940 (3) | 0.27924 (17) | 0.0470 (6) | |
C9 | 0.3387 (2) | 0.3096 (3) | 0.38577 (18) | 0.0520 (6) | |
C8 | 0.2721 (2) | 0.2613 (3) | 0.30193 (18) | 0.0518 (6) | |
H8 | 0.2039 | 0.2031 | 0.2909 | 0.062* | |
C11 | 0.5039 (2) | 0.4892 (3) | 0.25283 (19) | 0.0560 (7) | |
H11A | 0.5684 | 0.4167 | 0.2597 | 0.084* | |
H11B | 0.5257 | 0.5875 | 0.2938 | 0.084* | |
H11C | 0.4748 | 0.5263 | 0.1874 | 0.084* | |
C12 | 0.3348 (2) | 0.2954 (4) | 0.4840 (2) | 0.0699 (8) | |
H12A | 0.2632 | 0.2489 | 0.4839 | 0.105* | |
H12B | 0.3444 | 0.4070 | 0.5132 | 0.105* | |
H12C | 0.3942 | 0.2209 | 0.5197 | 0.105* | |
C13 | 0.5179 (2) | 0.1271 (3) | 0.13674 (17) | 0.0538 (6) | |
C14 | 0.6333 (2) | 0.0937 (4) | 0.1321 (2) | 0.0675 (8) | |
H14A | 0.6584 | −0.0172 | 0.1609 | 0.081* | 0.7 |
H14B | 0.6315 | 0.0881 | 0.0654 | 0.081* | 0.7 |
H14C | 0.6301 | 0.0638 | 0.0677 | 0.101* | 0.22 |
H14D | 0.6662 | 0.0006 | 0.1743 | 0.101* | 0.22 |
H14E | 0.6786 | 0.1949 | 0.1512 | 0.101* | 0.22 |
H14F | 0.6307 | 0.0229 | 0.0769 | 0.081* | 0.08 |
H14G | 0.6709 | 0.2007 | 0.1269 | 0.081* | 0.08 |
C16 | 0.4869 (2) | 0.0293 (4) | 0.2115 (2) | 0.0646 (7) | |
H16A | 0.5314 | 0.0685 | 0.2736 | 0.097* | 0.78 |
H16B | 0.5009 | −0.0907 | 0.2050 | 0.097* | 0.78 |
H16C | 0.4083 | 0.0464 | 0.2045 | 0.097* | 0.78 |
H16D | 0.4813 | 0.1036 | 0.2630 | 0.077* | 0.22 |
H16E | 0.4161 | −0.0311 | 0.1852 | 0.077* | 0.22 |
C15 | 0.7138 (3) | 0.2232 (5) | 0.1802 (3) | 0.0580 (10) | 0.7 |
H15A | 0.6895 | 0.3334 | 0.1522 | 0.087* | 0.7 |
H15B | 0.7865 | 0.1966 | 0.1735 | 0.087* | 0.7 |
H15C | 0.7189 | 0.2255 | 0.2470 | 0.087* | 0.7 |
C17 | 0.5772 (11) | −0.0852 (17) | 0.2428 (11) | 0.073 (4)* | 0.22 |
H17A | 0.5605 | −0.1886 | 0.2055 | 0.109* | 0.22 |
H17B | 0.5891 | −0.1119 | 0.3092 | 0.109* | 0.22 |
H17C | 0.6442 | −0.0335 | 0.2353 | 0.109* | 0.22 |
C18 | 0.6921 (17) | 0.007 (3) | 0.2186 (11) | 0.031 (5)* | 0.08 |
H18A | 0.7216 | 0.0892 | 0.2686 | 0.046* | 0.08 |
H18B | 0.7530 | −0.0589 | 0.2087 | 0.046* | 0.08 |
H18C | 0.6410 | −0.0690 | 0.2368 | 0.046* | 0.08 |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0675 (13) | 0.142 (2) | 0.0474 (12) | 0.0004 (13) | 0.0010 (10) | 0.0071 (13) |
C1 | 0.0604 (15) | 0.0667 (15) | 0.0358 (13) | −0.0013 (12) | 0.0201 (12) | −0.0008 (11) |
O2 | 0.0715 (12) | 0.0766 (12) | 0.0342 (9) | −0.0007 (10) | 0.0158 (9) | 0.0037 (8) |
C2 | 0.0544 (14) | 0.0591 (14) | 0.0365 (13) | −0.0033 (11) | 0.0178 (11) | −0.0022 (11) |
O3 | 0.0759 (12) | 0.0793 (13) | 0.0464 (11) | 0.0014 (10) | 0.0324 (10) | 0.0058 (9) |
C3 | 0.0522 (13) | 0.0616 (14) | 0.0370 (13) | −0.0071 (11) | 0.0116 (11) | 0.0000 (11) |
O4 | 0.0507 (9) | 0.0707 (11) | 0.0378 (9) | −0.0055 (8) | 0.0208 (7) | −0.0058 (8) |
C4 | 0.0624 (16) | 0.0774 (18) | 0.0421 (15) | −0.0034 (14) | 0.0111 (13) | 0.0017 (13) |
C5 | 0.0476 (12) | 0.0573 (14) | 0.0442 (14) | −0.0032 (11) | 0.0143 (11) | 0.0003 (11) |
C6 | 0.0489 (13) | 0.0805 (18) | 0.0547 (16) | −0.0050 (13) | 0.0138 (12) | 0.0023 (14) |
C7 | 0.0436 (11) | 0.0586 (13) | 0.0395 (13) | −0.0032 (10) | 0.0168 (10) | 0.0003 (11) |
C10 | 0.0466 (12) | 0.0616 (14) | 0.0379 (13) | −0.0009 (11) | 0.0201 (10) | −0.0014 (11) |
C9 | 0.0502 (13) | 0.0674 (15) | 0.0450 (14) | −0.0003 (12) | 0.0246 (11) | 0.0023 (12) |
C8 | 0.0488 (13) | 0.0629 (14) | 0.0493 (15) | −0.0031 (11) | 0.0232 (12) | 0.0011 (12) |
C11 | 0.0537 (14) | 0.0728 (16) | 0.0460 (14) | −0.0127 (13) | 0.0219 (12) | −0.0061 (13) |
C12 | 0.0687 (18) | 0.103 (2) | 0.0474 (16) | −0.0059 (16) | 0.0324 (14) | −0.0003 (15) |
C13 | 0.0589 (15) | 0.0675 (15) | 0.0389 (13) | 0.0040 (12) | 0.0208 (12) | −0.0010 (11) |
C14 | 0.0710 (18) | 0.0850 (19) | 0.0557 (17) | 0.0184 (15) | 0.0329 (14) | 0.0125 (15) |
C16 | 0.0757 (17) | 0.0739 (18) | 0.0516 (16) | 0.0135 (15) | 0.0306 (14) | 0.0160 (14) |
C15 | 0.0474 (19) | 0.086 (3) | 0.045 (2) | 0.0088 (18) | 0.0206 (16) | −0.0034 (19) |
O1—C4 | 1.204 (3) | C12—H12C | 0.9800 |
C1—O3 | 1.200 (3) | C13—C16 | 1.507 (4) |
C1—O2 | 1.398 (3) | C13—C14 | 1.511 (4) |
C1—C2 | 1.472 (3) | C14—C18 | 1.458 (10) |
O2—C4 | 1.396 (3) | C14—C15 | 1.476 (5) |
C2—C13 | 1.353 (3) | C14—H14A | 0.9900 |
C2—C3 | 1.483 (3) | C14—H14B | 0.9900 |
C3—C5 | 1.367 (3) | C14—H14C | 0.9800 |
C3—C4 | 1.480 (4) | C14—H14D | 0.9800 |
O4—C10 | 1.376 (3) | C14—H14E | 0.9800 |
O4—C9 | 1.380 (3) | C14—H14F | 0.9900 |
C5—C7 | 1.465 (3) | C14—H14G | 0.9900 |
C5—C6 | 1.515 (3) | C16—C17 | 1.427 (13) |
C6—H6A | 0.9800 | C16—H16A | 0.9800 |
C6—H6B | 0.9800 | C16—H16B | 0.9800 |
C6—H6C | 0.9800 | C16—H16C | 0.9800 |
C7—C10 | 1.369 (3) | C16—H16D | 0.9900 |
C7—C8 | 1.445 (3) | C16—H16E | 0.9900 |
C10—C11 | 1.480 (3) | C15—H15A | 0.9800 |
C9—C8 | 1.339 (4) | C15—H15B | 0.9800 |
C9—C12 | 1.488 (4) | C15—H15C | 0.9800 |
C8—H8 | 0.9500 | C17—H17A | 0.9800 |
C11—H11A | 0.9800 | C17—H17B | 0.9800 |
C11—H11B | 0.9800 | C17—H17C | 0.9800 |
C11—H11C | 0.9800 | C18—H18A | 0.9800 |
C12—H12A | 0.9800 | C18—H18B | 0.9800 |
C12—H12B | 0.9800 | C18—H18C | 0.9800 |
O3—C1—O2 | 118.8 (2) | C16—C13—C14 | 114.6 (2) |
O3—C1—C2 | 132.9 (2) | C18—C14—C13 | 106.6 (9) |
O2—C1—C2 | 108.3 (2) | C15—C14—C13 | 113.1 (3) |
C4—O2—C1 | 110.2 (2) | C15—C14—H14A | 109.0 |
C13—C2—C1 | 121.5 (2) | C13—C14—H14A | 109.0 |
C13—C2—C3 | 131.1 (2) | C15—C14—H14B | 109.0 |
C1—C2—C3 | 105.7 (2) | C13—C14—H14B | 109.0 |
C5—C3—C4 | 121.5 (2) | H14A—C14—H14B | 107.8 |
C5—C3—C2 | 133.1 (2) | C13—C14—H14C | 109.5 |
C4—C3—C2 | 104.8 (2) | C13—C14—H14D | 109.5 |
C10—O4—C9 | 107.47 (18) | H14C—C14—H14D | 109.5 |
O1—C4—O2 | 118.4 (3) | C13—C14—H14E | 109.5 |
O1—C4—C3 | 132.9 (3) | H14C—C14—H14E | 109.5 |
O2—C4—C3 | 108.6 (2) | H14D—C14—H14E | 109.5 |
C3—C5—C7 | 124.7 (2) | C18—C14—H14F | 110.4 |
C3—C5—C6 | 121.7 (2) | C13—C14—H14F | 110.4 |
C7—C5—C6 | 113.6 (2) | C18—C14—H14G | 110.4 |
C5—C6—H6A | 109.5 | C13—C14—H14G | 110.4 |
C5—C6—H6B | 109.5 | H14F—C14—H14G | 108.6 |
H6A—C6—H6B | 109.5 | C17—C16—C13 | 102.1 (6) |
C5—C6—H6C | 109.5 | C13—C16—H16A | 109.5 |
H6A—C6—H6C | 109.5 | C13—C16—H16B | 109.5 |
H6B—C6—H6C | 109.5 | H16A—C16—H16B | 109.5 |
C10—C7—C8 | 105.3 (2) | C13—C16—H16C | 109.5 |
C10—C7—C5 | 128.0 (2) | H16A—C16—H16C | 109.5 |
C8—C7—C5 | 126.3 (2) | H16B—C16—H16C | 109.5 |
C7—C10—O4 | 109.80 (19) | C17—C16—H16D | 111.3 |
C7—C10—C11 | 135.3 (2) | C13—C16—H16D | 111.3 |
O4—C10—C11 | 114.8 (2) | C17—C16—H16E | 111.3 |
C8—C9—O4 | 109.3 (2) | C13—C16—H16E | 111.3 |
C8—C9—C12 | 134.6 (2) | H16D—C16—H16E | 109.2 |
O4—C9—C12 | 116.1 (2) | C14—C15—H15A | 109.5 |
C9—C8—C7 | 108.1 (2) | C14—C15—H15B | 109.5 |
C9—C8—H8 | 125.9 | H15A—C15—H15B | 109.5 |
C7—C8—H8 | 125.9 | C14—C15—H15C | 109.5 |
C10—C11—H11A | 109.5 | H15A—C15—H15C | 109.5 |
C10—C11—H11B | 109.5 | H15B—C15—H15C | 109.5 |
H11A—C11—H11B | 109.5 | C16—C17—H17A | 109.5 |
C10—C11—H11C | 109.5 | C16—C17—H17B | 109.5 |
H11A—C11—H11C | 109.5 | H17A—C17—H17B | 109.5 |
H11B—C11—H11C | 109.5 | C16—C17—H17C | 109.5 |
C9—C12—H12A | 109.5 | H17A—C17—H17C | 109.5 |
C9—C12—H12B | 109.5 | H17B—C17—H17C | 109.5 |
H12A—C12—H12B | 109.5 | C14—C18—H18A | 109.5 |
C9—C12—H12C | 109.5 | C14—C18—H18B | 109.5 |
H12A—C12—H12C | 109.5 | H18A—C18—H18B | 109.5 |
H12B—C12—H12C | 109.5 | C14—C18—H18C | 109.5 |
C2—C13—C16 | 122.6 (2) | H18A—C18—H18C | 109.5 |
C2—C13—C14 | 122.8 (2) | H18B—C18—H18C | 109.5 |
O3—C1—O2—C4 | −176.7 (2) | C6—C5—C7—C8 | 32.6 (3) |
C2—C1—O2—C4 | 4.8 (3) | C8—C7—C10—O4 | 0.7 (3) |
O3—C1—C2—C13 | −24.3 (4) | C5—C7—C10—O4 | 173.3 (2) |
O2—C1—C2—C13 | 153.9 (2) | C8—C7—C10—C11 | −174.3 (3) |
O3—C1—C2—C3 | 169.0 (3) | C5—C7—C10—C11 | −1.7 (5) |
O2—C1—C2—C3 | −12.7 (3) | C9—O4—C10—C7 | −0.1 (3) |
C13—C2—C3—C5 | 39.6 (5) | C9—O4—C10—C11 | 176.1 (2) |
C1—C2—C3—C5 | −155.5 (3) | C10—O4—C9—C8 | −0.6 (3) |
C13—C2—C3—C4 | −149.5 (3) | C10—O4—C9—C12 | −179.6 (2) |
C1—C2—C3—C4 | 15.3 (3) | O4—C9—C8—C7 | 1.0 (3) |
C1—O2—C4—O1 | −176.2 (3) | C12—C9—C8—C7 | 179.8 (3) |
C1—O2—C4—C3 | 5.3 (3) | C10—C7—C8—C9 | −1.1 (3) |
C5—C3—C4—O1 | −19.1 (5) | C5—C7—C8—C9 | −173.8 (2) |
C2—C3—C4—O1 | 168.8 (3) | C1—C2—C13—C16 | −165.7 (3) |
C5—C3—C4—O2 | 159.2 (2) | C3—C2—C13—C16 | −2.9 (4) |
C2—C3—C4—O2 | −13.0 (3) | C1—C2—C13—C14 | 12.9 (4) |
C4—C3—C5—C7 | −159.8 (2) | C3—C2—C13—C14 | 175.8 (3) |
C2—C3—C5—C7 | 9.7 (4) | C2—C13—C14—C18 | 166.8 (10) |
C4—C3—C5—C6 | 18.4 (4) | C16—C13—C14—C18 | −14.4 (10) |
C2—C3—C5—C6 | −172.1 (3) | C2—C13—C14—C15 | 82.2 (4) |
C3—C5—C7—C10 | 39.8 (4) | C16—C13—C14—C15 | −99.1 (3) |
C6—C5—C7—C10 | −138.6 (3) | C2—C13—C16—C17 | 169.6 (7) |
C3—C5—C7—C8 | −149.1 (3) | C14—C13—C16—C17 | −9.1 (7) |
C17H18O4 | F(000) = 608 |
Mr = 286.31 | Dx = 1.299 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71075 Å |
a = 12.3175 (7) Å | Cell parameters from 11394 reflections |
b = 8.1863 (4) Å | θ = 3.0–27.4° |
c = 15.1293 (8) Å | µ = 0.09 mm−1 |
β = 106.327 (1)° | T = 173 K |
V = 1464.04 (13) Å3 | Rods, yellow |
Z = 4 | 0.29 × 0.19 × 0.11 mm |
Rigaku RAXIS-RAPID Imaging Plate diffractometer | 2764 reflections with I > 2σ(I) |
Oscillation Photograph scans | Rint = 0.027 |
Absorption correction: multi scan ABSCOR (Higashi, 1995) | θmax = 27.4°, θmin = 3.0° |
Tmin = 0.860, Tmax = 0.968 | h = −14→15 |
13814 measured reflections | k = −10→10 |
3340 independent reflections | l = −19→19 |
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)] = 0.045 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.127 | H-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 parameters | Δρmax = 0.35 e Å−3 |
0 restraints | Δρmin = −0.18 e Å−3 |
C17H18O4 | V = 1464.04 (13) Å3 |
Mr = 286.31 | Z = 4 |
Monoclinic, P21/n | Mo Kα radiation |
a = 12.3175 (7) Å | µ = 0.09 mm−1 |
b = 8.1863 (4) Å | T = 173 K |
c = 15.1293 (8) Å | 0.29 × 0.19 × 0.11 mm |
β = 106.327 (1)° |
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 = 0.968 | Rint = 0.027 |
13814 measured reflections |
R[F2 > 2σ(F2)] = 0.045 | 0 restraints |
wR(F2) = 0.127 | H-atom parameters constrained |
S = 1.08 | Δρmax = 0.35 e Å−3 |
3340 reflections | Δρmin = −0.18 e Å−3 |
193 parameters |
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 |
x | y | z | Uiso*/Ueq | ||
O1 | 0.17754 (10) | 0.3614 (2) | −0.07081 (7) | 0.0641 (4) | |
O2 | 0.35993 (8) | 0.34821 (13) | −0.06750 (6) | 0.0395 (3) | |
O3 | 0.54775 (9) | 0.31349 (14) | −0.02929 (6) | 0.0410 (3) | |
O4 | 0.42652 (7) | 0.40079 (12) | 0.37465 (6) | 0.0317 (2) | |
C1 | 0.27252 (12) | 0.3355 (2) | −0.02548 (9) | 0.0397 (3) | |
C2 | 0.32283 (10) | 0.29451 (16) | 0.07301 (8) | 0.0293 (3) | |
C3 | 0.44113 (10) | 0.25109 (15) | 0.08094 (7) | 0.0265 (3) | |
C4 | 0.46269 (11) | 0.30594 (16) | −0.00575 (8) | 0.0317 (3) | |
C5 | 0.51535 (10) | 0.15205 (15) | 0.13956 (8) | 0.0260 (3) | |
C6 | 0.63082 (10) | 0.10485 (17) | 0.13030 (8) | 0.0323 (3) | |
H6A | 0.6785 | 0.2029 | 0.1324 | 0.039* | |
H6B | 0.6235 | 0.0465 | 0.0716 | 0.039* | |
C7 | 0.68212 (11) | −0.00743 (18) | 0.21294 (9) | 0.0363 (3) | |
H7A | 0.7293 | −0.0936 | 0.1964 | 0.044* | |
H7B | 0.7291 | 0.0557 | 0.2657 | 0.044* | |
C8 | 0.57941 (11) | −0.08147 (16) | 0.23591 (9) | 0.0336 (3) | |
H8A | 0.5991 | −0.1182 | 0.3008 | 0.040* | |
H8B | 0.5490 | −0.1753 | 0.1952 | 0.040* | |
C9 | 0.49383 (10) | 0.06003 (16) | 0.21902 (8) | 0.0282 (3) | |
H9A | 0.4153 | 0.0182 | 0.2030 | 0.034* | |
H9B | 0.5070 | 0.1306 | 0.2742 | 0.034* | |
C10 | 0.26377 (10) | 0.31375 (16) | 0.13661 (8) | 0.0292 (3) | |
C11 | 0.13623 (11) | 0.3329 (2) | 0.10719 (10) | 0.0401 (3) | |
H11A | 0.1167 | 0.4475 | 0.1136 | 0.060* | |
H11B | 0.1034 | 0.2645 | 0.1462 | 0.060* | |
H11C | 0.1062 | 0.2993 | 0.0428 | 0.060* | |
C12 | 0.31553 (10) | 0.32528 (15) | 0.23606 (8) | 0.0270 (3) | |
C13 | 0.26423 (11) | 0.27481 (17) | 0.30698 (9) | 0.0320 (3) | |
H13 | 0.1941 | 0.2194 | 0.2976 | 0.038* | |
C14 | 0.33400 (11) | 0.32072 (18) | 0.38825 (9) | 0.0343 (3) | |
C15 | 0.33068 (14) | 0.3057 (3) | 0.48586 (10) | 0.0538 (5) | |
H15A | 0.2567 | 0.2636 | 0.4872 | 0.081* | |
H15B | 0.3431 | 0.4132 | 0.5155 | 0.081* | |
H15C | 0.3901 | 0.2303 | 0.5190 | 0.081* | |
C16 | 0.50322 (11) | 0.49045 (17) | 0.25283 (9) | 0.0355 (3) | |
H16A | 0.5648 | 0.4148 | 0.2526 | 0.053* | |
H16B | 0.5326 | 0.5798 | 0.2960 | 0.053* | |
H16C | 0.4714 | 0.5351 | 0.1908 | 0.053* | |
C17 | 0.41391 (10) | 0.40237 (15) | 0.28159 (8) | 0.0276 (3) |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0412 (6) | 0.1118 (12) | 0.0321 (5) | 0.0099 (6) | −0.0015 (4) | 0.0151 (6) |
O2 | 0.0444 (6) | 0.0524 (6) | 0.0213 (4) | 0.0011 (4) | 0.0088 (4) | 0.0049 (4) |
O3 | 0.0458 (6) | 0.0523 (6) | 0.0309 (5) | −0.0026 (4) | 0.0209 (4) | 0.0039 (4) |
O4 | 0.0300 (5) | 0.0421 (5) | 0.0249 (4) | −0.0027 (4) | 0.0106 (3) | −0.0043 (4) |
C1 | 0.0391 (7) | 0.0528 (9) | 0.0253 (6) | 0.0006 (6) | 0.0061 (5) | 0.0034 (6) |
C2 | 0.0280 (6) | 0.0354 (7) | 0.0228 (5) | −0.0020 (5) | 0.0044 (4) | 0.0010 (5) |
C3 | 0.0298 (6) | 0.0305 (6) | 0.0206 (5) | −0.0051 (5) | 0.0094 (4) | −0.0025 (5) |
C4 | 0.0405 (7) | 0.0339 (6) | 0.0218 (5) | −0.0032 (5) | 0.0107 (5) | −0.0010 (5) |
C5 | 0.0277 (6) | 0.0297 (6) | 0.0215 (5) | −0.0052 (4) | 0.0084 (4) | −0.0049 (4) |
C6 | 0.0298 (6) | 0.0399 (7) | 0.0297 (6) | −0.0014 (5) | 0.0128 (5) | −0.0038 (5) |
C7 | 0.0316 (6) | 0.0455 (8) | 0.0312 (6) | 0.0055 (5) | 0.0077 (5) | −0.0042 (6) |
C8 | 0.0403 (7) | 0.0317 (7) | 0.0288 (6) | 0.0027 (5) | 0.0097 (5) | 0.0007 (5) |
C9 | 0.0288 (6) | 0.0321 (6) | 0.0246 (5) | −0.0016 (5) | 0.0092 (4) | 0.0015 (5) |
C10 | 0.0262 (6) | 0.0332 (6) | 0.0275 (6) | −0.0023 (5) | 0.0065 (4) | 0.0004 (5) |
C11 | 0.0262 (6) | 0.0564 (9) | 0.0364 (7) | 0.0004 (6) | 0.0066 (5) | 0.0013 (6) |
C12 | 0.0250 (6) | 0.0303 (6) | 0.0275 (6) | 0.0013 (4) | 0.0102 (4) | 0.0000 (5) |
C13 | 0.0260 (6) | 0.0402 (7) | 0.0330 (6) | −0.0006 (5) | 0.0133 (5) | 0.0009 (5) |
C14 | 0.0292 (6) | 0.0471 (8) | 0.0305 (6) | 0.0009 (5) | 0.0147 (5) | 0.0009 (5) |
C15 | 0.0434 (9) | 0.0924 (14) | 0.0307 (7) | −0.0052 (8) | 0.0187 (6) | 0.0003 (8) |
C16 | 0.0362 (7) | 0.0381 (7) | 0.0342 (6) | −0.0113 (5) | 0.0131 (5) | −0.0049 (5) |
C17 | 0.0293 (6) | 0.0306 (6) | 0.0245 (5) | 0.0001 (5) | 0.0100 (4) | −0.0016 (5) |
O1—C1 | 1.1970 (18) | C8—H8B | 0.9900 |
O2—C4 | 1.3891 (16) | C9—H9A | 0.9900 |
O2—C1 | 1.3995 (17) | C9—H9B | 0.9900 |
O3—C4 | 1.1993 (16) | C10—C12 | 1.4629 (16) |
O4—C17 | 1.3724 (14) | C10—C11 | 1.5158 (17) |
O4—C14 | 1.3793 (16) | C11—H11A | 0.9800 |
C1—C2 | 1.4826 (17) | C11—H11B | 0.9800 |
C2—C10 | 1.3687 (17) | C11—H11C | 0.9800 |
C2—C3 | 1.4717 (17) | C12—C17 | 1.3681 (17) |
C3—C5 | 1.3505 (17) | C12—C13 | 1.4500 (16) |
C3—C4 | 1.4793 (15) | C13—C14 | 1.3407 (19) |
C5—C9 | 1.5040 (16) | C13—H13 | 0.9500 |
C5—C6 | 1.5178 (17) | C14—C15 | 1.4939 (18) |
C6—C7 | 1.5372 (19) | C15—H15A | 0.9800 |
C6—H6A | 0.9900 | C15—H15B | 0.9800 |
C6—H6B | 0.9900 | C15—H15C | 0.9800 |
C7—C8 | 1.5283 (19) | C16—C17 | 1.4794 (17) |
C7—H7A | 0.9900 | C16—H16A | 0.9800 |
C7—H7B | 0.9900 | C16—H16B | 0.9800 |
C8—C9 | 1.5385 (18) | C16—H16C | 0.9800 |
C8—H8A | 0.9900 | ||
C4—O2—C1 | 110.36 (9) | C8—C9—H9A | 110.9 |
C17—O4—C14 | 107.31 (9) | C5—C9—H9B | 110.9 |
O1—C1—O2 | 118.65 (12) | C8—C9—H9B | 110.9 |
O1—C1—C2 | 132.92 (14) | H9A—C9—H9B | 109.0 |
O2—C1—C2 | 108.41 (11) | C2—C10—C12 | 124.50 (11) |
C10—C2—C3 | 132.86 (11) | C2—C10—C11 | 121.16 (11) |
C10—C2—C1 | 121.73 (12) | C12—C10—C11 | 114.29 (11) |
C3—C2—C1 | 105.14 (10) | C10—C11—H11A | 109.5 |
C5—C3—C2 | 132.11 (11) | C10—C11—H11B | 109.5 |
C5—C3—C4 | 120.49 (11) | H11A—C11—H11B | 109.5 |
C2—C3—C4 | 105.95 (10) | C10—C11—H11C | 109.5 |
O3—C4—O2 | 119.63 (11) | H11A—C11—H11C | 109.5 |
O3—C4—C3 | 131.95 (12) | H11B—C11—H11C | 109.5 |
O2—C4—C3 | 108.37 (10) | C17—C12—C13 | 105.52 (10) |
C3—C5—C9 | 125.93 (11) | C17—C12—C10 | 128.01 (11) |
C3—C5—C6 | 124.83 (10) | C13—C12—C10 | 126.02 (11) |
C9—C5—C6 | 109.06 (10) | C14—C13—C12 | 107.36 (11) |
C5—C6—C7 | 104.99 (10) | C14—C13—H13 | 126.3 |
C5—C6—H6A | 110.7 | C12—C13—H13 | 126.3 |
C7—C6—H6A | 110.7 | C13—C14—O4 | 109.87 (11) |
C5—C6—H6B | 110.7 | C13—C14—C15 | 134.01 (13) |
C7—C6—H6B | 110.7 | O4—C14—C15 | 116.11 (12) |
H6A—C6—H6B | 108.8 | C14—C15—H15A | 109.5 |
C8—C7—C6 | 104.17 (10) | C14—C15—H15B | 109.5 |
C8—C7—H7A | 110.9 | H15A—C15—H15B | 109.5 |
C6—C7—H7A | 110.9 | C14—C15—H15C | 109.5 |
C8—C7—H7B | 110.9 | H15A—C15—H15C | 109.5 |
C6—C7—H7B | 110.9 | H15B—C15—H15C | 109.5 |
H7A—C7—H7B | 108.9 | C17—C16—H16A | 109.5 |
C7—C8—C9 | 103.65 (10) | C17—C16—H16B | 109.5 |
C7—C8—H8A | 111.0 | H16A—C16—H16B | 109.5 |
C9—C8—H8A | 111.0 | C17—C16—H16C | 109.5 |
C7—C8—H8B | 111.0 | H16A—C16—H16C | 109.5 |
C9—C8—H8B | 111.0 | H16B—C16—H16C | 109.5 |
H8A—C8—H8B | 109.0 | C12—C17—O4 | 109.93 (10) |
C5—C9—C8 | 104.09 (10) | C12—C17—C16 | 134.70 (11) |
C5—C9—H9A | 110.9 | O4—C17—C16 | 115.29 (10) |
C4—O2—C1—O1 | −176.97 (15) | C3—C5—C9—C8 | 157.19 (12) |
C4—O2—C1—C2 | 4.72 (16) | C6—C5—C9—C8 | −17.99 (13) |
O1—C1—C2—C10 | −14.6 (3) | C7—C8—C9—C5 | 34.04 (12) |
O2—C1—C2—C10 | 163.41 (12) | C3—C2—C10—C12 | 12.9 (2) |
O1—C1—C2—C3 | 170.66 (19) | C1—C2—C10—C12 | −160.20 (13) |
O2—C1—C2—C3 | −11.36 (15) | C3—C2—C10—C11 | −170.02 (13) |
C10—C2—C3—C5 | 33.5 (2) | C1—C2—C10—C11 | 16.9 (2) |
C1—C2—C3—C5 | −152.53 (13) | C2—C10—C12—C17 | 37.9 (2) |
C10—C2—C3—C4 | −160.61 (14) | C11—C10—C12—C17 | −139.35 (14) |
C1—C2—C3—C4 | 13.32 (14) | C2—C10—C12—C13 | −150.94 (13) |
C1—O2—C4—O3 | −178.23 (13) | C11—C10—C12—C13 | 31.81 (18) |
C1—O2—C4—C3 | 3.96 (15) | C17—C12—C13—C14 | −1.10 (15) |
C5—C3—C4—O3 | −20.6 (2) | C10—C12—C13—C14 | −173.88 (13) |
C2—C3—C4—O3 | 171.56 (14) | C12—C13—C14—O4 | 1.16 (15) |
C5—C3—C4—O2 | 156.84 (11) | C12—C13—C14—C15 | 179.96 (17) |
C2—C3—C4—O2 | −11.01 (13) | C17—O4—C14—C13 | −0.78 (15) |
C2—C3—C5—C9 | −2.5 (2) | C17—O4—C14—C15 | −179.82 (13) |
C4—C3—C5—C9 | −166.64 (11) | C13—C12—C17—O4 | 0.63 (14) |
C2—C3—C5—C6 | 171.98 (12) | C10—C12—C17—O4 | 173.22 (11) |
C4—C3—C5—C6 | 7.81 (18) | C13—C12—C17—C16 | −175.92 (14) |
C3—C5—C6—C7 | 179.76 (11) | C10—C12—C17—C16 | −3.3 (2) |
C9—C5—C6—C7 | −4.99 (13) | C14—O4—C17—C12 | 0.05 (14) |
C5—C6—C7—C8 | 26.19 (13) | C14—O4—C17—C16 | 177.34 (11) |
C6—C7—C8—C9 | −37.36 (12) |
C18H20O4 | F(000) = 640 |
Mr = 300.34 | Dx = 1.262 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71075 Å |
a = 9.6047 (7) Å | Cell parameters from 8916 reflections |
b = 14.4631 (10) Å | θ = 3.1–27.4° |
c = 11.3814 (8) Å | µ = 0.09 mm−1 |
β = 91.355 (2)° | T = 173 K |
V = 1580.59 (19) Å3 | Plates, white |
Z = 4 | 0.31 × 0.17 × 0.07 mm |
Rigaku RAXIS-RAPID Imaging Plate diffractometer | 1915 reflections with I > 2σ(I) |
Oscillation Photograph scans | Rint = 0.047 |
Absorption correction: multi-scan ABSCOR (Higashi, 1995) | θmax = 27.4°, θmin = 3.1° |
Tmin = 0.872, Tmax = 0.894 | h = −12→12 |
15155 measured reflections | k = −18→18 |
3582 independent reflections | l = −14→14 |
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)] = 0.042 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.130 | H-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 parameters | Δρmax = 0.18 e Å−3 |
0 restraints | Δρmin = −0.18 e Å−3 |
C18H20O4 | V = 1580.59 (19) Å3 |
Mr = 300.34 | Z = 4 |
Monoclinic, P21/n | Mo Kα radiation |
a = 9.6047 (7) Å | µ = 0.09 mm−1 |
b = 14.4631 (10) Å | T = 173 K |
c = 11.3814 (8) Å | 0.31 × 0.17 × 0.07 mm |
β = 91.355 (2)° |
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 = 0.894 | Rint = 0.047 |
15155 measured reflections |
R[F2 > 2σ(F2)] = 0.042 | 0 restraints |
wR(F2) = 0.130 | H-atom parameters constrained |
S = 1.04 | Δρmax = 0.18 e Å−3 |
3582 reflections | Δρmin = −0.18 e Å−3 |
202 parameters |
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 |
x | y | z | Uiso*/Ueq | ||
O1 | −0.07867 (15) | 0.91017 (10) | 0.34554 (11) | 0.0724 (4) | |
O2 | 0.02297 (17) | 0.78884 (12) | 0.26017 (12) | 0.0878 (5) | |
O3 | −0.17927 (17) | 1.00915 (10) | 0.46856 (14) | 0.0867 (5) | |
O4 | 0.08630 (12) | 0.68720 (8) | 0.80884 (9) | 0.0547 (3) | |
C1 | −0.0387 (2) | 0.81726 (16) | 0.34344 (16) | 0.0622 (5) | |
C2 | −0.09090 (17) | 0.77254 (12) | 0.45014 (14) | 0.0495 (4) | |
C3 | −0.12909 (17) | 0.84941 (12) | 0.52834 (14) | 0.0489 (4) | |
C4 | −0.1382 (2) | 0.93195 (15) | 0.45264 (17) | 0.0622 (5) | |
C5 | −0.13068 (17) | 0.85484 (11) | 0.64775 (15) | 0.0495 (4) | |
C6 | −0.1895 (2) | 0.93696 (13) | 0.71089 (17) | 0.0698 (6) | |
H6A | −0.1142 | 0.9697 | 0.7530 | 0.105* | |
H6B | −0.2584 | 0.9159 | 0.7671 | 0.105* | |
H6C | −0.2343 | 0.9787 | 0.6537 | 0.105* | |
C7 | −0.06896 (17) | 0.78333 (11) | 0.72474 (14) | 0.0472 (4) | |
C8 | 0.05817 (18) | 0.74326 (12) | 0.71333 (14) | 0.0487 (4) | |
C9 | 0.17005 (19) | 0.75015 (14) | 0.62634 (16) | 0.0607 (5) | |
H9A | 0.1613 | 0.6990 | 0.5701 | 0.091* | |
H9B | 0.2610 | 0.7469 | 0.6670 | 0.091* | |
H9C | 0.1618 | 0.8091 | 0.5843 | 0.091* | |
C10 | −0.12098 (19) | 0.75029 (13) | 0.83461 (15) | 0.0551 (5) | |
H10 | −0.2073 | 0.7667 | 0.8679 | 0.066* | |
C11 | −0.02661 (19) | 0.69245 (13) | 0.88156 (14) | 0.0543 (4) | |
C12 | −0.0147 (2) | 0.63655 (16) | 0.99144 (17) | 0.0762 (6) | |
H12A | 0.0425 | 0.6699 | 1.0499 | 0.114* | |
H12B | 0.0289 | 0.5770 | 0.9742 | 0.114* | |
H12C | −0.1077 | 0.6260 | 1.0224 | 0.114* | |
C13 | −0.12334 (18) | 0.68165 (13) | 0.45707 (14) | 0.0523 (4) | |
C14 | −0.2131 (2) | 0.64378 (13) | 0.55156 (15) | 0.0590 (5) | |
H14A | −0.2529 | 0.6956 | 0.5967 | 0.071* | |
H14B | −0.1554 | 0.6059 | 0.6064 | 0.071* | |
C15 | −0.3317 (2) | 0.58429 (14) | 0.49970 (18) | 0.0689 (6) | |
H15A | −0.3856 | 0.5573 | 0.5644 | 0.083* | |
H15B | −0.3954 | 0.6238 | 0.4519 | 0.083* | |
C16 | −0.2764 (3) | 0.50747 (14) | 0.4238 (2) | 0.0839 (7) | |
H16A | −0.2170 | 0.4658 | 0.4724 | 0.101* | |
H16B | −0.3552 | 0.4708 | 0.3909 | 0.101* | |
C17 | −0.1928 (3) | 0.54651 (16) | 0.32525 (19) | 0.0859 (7) | |
H17A | −0.2554 | 0.5818 | 0.2714 | 0.103* | |
H17B | −0.1522 | 0.4950 | 0.2801 | 0.103* | |
C18 | −0.0752 (2) | 0.61012 (15) | 0.37018 (17) | 0.0725 (6) | |
H18A | −0.0014 | 0.5719 | 0.4080 | 0.087* | |
H18B | −0.0341 | 0.6421 | 0.3024 | 0.087* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0685 (9) | 0.0853 (10) | 0.0629 (8) | −0.0112 (8) | −0.0077 (7) | 0.0252 (7) |
O2 | 0.0784 (10) | 0.1305 (14) | 0.0551 (8) | −0.0160 (10) | 0.0132 (7) | −0.0013 (8) |
O3 | 0.0918 (12) | 0.0604 (9) | 0.1071 (11) | 0.0091 (8) | −0.0149 (9) | 0.0195 (8) |
O4 | 0.0490 (7) | 0.0611 (7) | 0.0537 (7) | 0.0021 (6) | −0.0027 (6) | 0.0060 (6) |
C1 | 0.0494 (11) | 0.0877 (15) | 0.0492 (11) | −0.0106 (10) | −0.0078 (9) | 0.0052 (10) |
C2 | 0.0408 (9) | 0.0636 (11) | 0.0437 (9) | −0.0014 (8) | −0.0060 (7) | 0.0010 (8) |
C3 | 0.0406 (9) | 0.0528 (10) | 0.0531 (9) | −0.0002 (8) | −0.0047 (7) | 0.0064 (8) |
C4 | 0.0520 (11) | 0.0639 (13) | 0.0700 (12) | −0.0042 (10) | −0.0143 (9) | 0.0122 (10) |
C5 | 0.0422 (9) | 0.0491 (9) | 0.0571 (10) | −0.0011 (8) | −0.0016 (8) | −0.0030 (8) |
C6 | 0.0757 (14) | 0.0612 (12) | 0.0726 (12) | 0.0102 (10) | 0.0045 (11) | −0.0090 (10) |
C7 | 0.0437 (9) | 0.0514 (9) | 0.0463 (9) | −0.0022 (8) | −0.0031 (7) | −0.0035 (7) |
C8 | 0.0468 (10) | 0.0532 (10) | 0.0458 (9) | −0.0018 (8) | −0.0042 (7) | 0.0006 (7) |
C9 | 0.0473 (10) | 0.0758 (13) | 0.0591 (11) | 0.0048 (9) | 0.0032 (9) | 0.0049 (9) |
C10 | 0.0446 (10) | 0.0693 (12) | 0.0514 (9) | 0.0006 (9) | 0.0019 (8) | −0.0013 (8) |
C11 | 0.0490 (10) | 0.0642 (11) | 0.0497 (9) | −0.0055 (9) | 0.0002 (8) | 0.0023 (8) |
C12 | 0.0683 (14) | 0.0907 (16) | 0.0695 (12) | 0.0004 (12) | 0.0023 (10) | 0.0244 (11) |
C13 | 0.0496 (10) | 0.0606 (11) | 0.0462 (9) | 0.0031 (9) | −0.0097 (8) | −0.0039 (8) |
C14 | 0.0672 (12) | 0.0554 (11) | 0.0541 (10) | −0.0048 (9) | −0.0063 (9) | 0.0010 (8) |
C15 | 0.0706 (14) | 0.0610 (12) | 0.0746 (12) | −0.0107 (10) | −0.0122 (10) | 0.0066 (10) |
C16 | 0.1003 (18) | 0.0614 (13) | 0.0884 (15) | −0.0061 (12) | −0.0312 (14) | −0.0047 (12) |
C17 | 0.1041 (19) | 0.0776 (15) | 0.0748 (14) | 0.0061 (14) | −0.0209 (13) | −0.0245 (12) |
C18 | 0.0769 (15) | 0.0754 (13) | 0.0650 (12) | 0.0109 (11) | −0.0039 (10) | −0.0160 (11) |
O1—C4 | 1.395 (2) | C10—C11 | 1.336 (3) |
O1—C1 | 1.398 (3) | C10—H10 | 0.9500 |
O2—C1 | 1.202 (2) | C11—C12 | 1.491 (2) |
O3—C4 | 1.199 (2) | C12—H12A | 0.9800 |
O4—C8 | 1.3777 (19) | C12—H12B | 0.9800 |
O4—C11 | 1.382 (2) | C12—H12C | 0.9800 |
C1—C2 | 1.474 (2) | C13—C14 | 1.498 (2) |
C2—C13 | 1.354 (2) | C13—C18 | 1.511 (2) |
C2—C3 | 1.476 (2) | C14—C15 | 1.534 (3) |
C3—C5 | 1.362 (2) | C14—H14A | 0.9900 |
C3—C4 | 1.474 (3) | C14—H14B | 0.9900 |
C5—C7 | 1.471 (2) | C15—C16 | 1.511 (3) |
C5—C6 | 1.505 (2) | C15—H15A | 0.9900 |
C6—H6A | 0.9800 | C15—H15B | 0.9900 |
C6—H6B | 0.9800 | C16—C17 | 1.505 (3) |
C6—H6C | 0.9800 | C16—H16A | 0.9900 |
C7—C8 | 1.361 (2) | C16—H16B | 0.9900 |
C7—C10 | 1.439 (2) | C17—C18 | 1.535 (3) |
C8—C9 | 1.482 (2) | C17—H17A | 0.9900 |
C9—H9A | 0.9800 | C17—H17B | 0.9900 |
C9—H9B | 0.9800 | C18—H18A | 0.9900 |
C9—H9C | 0.9800 | C18—H18B | 0.9900 |
C4—O1—C1 | 110.53 (14) | O4—C11—C12 | 115.26 (16) |
C8—O4—C11 | 107.35 (13) | C11—C12—H12A | 109.5 |
O2—C1—O1 | 118.88 (18) | C11—C12—H12B | 109.5 |
O2—C1—C2 | 133.1 (2) | H12A—C12—H12B | 109.5 |
O1—C1—C2 | 107.97 (16) | C11—C12—H12C | 109.5 |
C13—C2—C1 | 123.86 (16) | H12A—C12—H12C | 109.5 |
C13—C2—C3 | 129.47 (15) | H12B—C12—H12C | 109.5 |
C1—C2—C3 | 105.10 (16) | C2—C13—C14 | 122.28 (16) |
C5—C3—C4 | 122.34 (16) | C2—C13—C18 | 123.53 (17) |
C5—C3—C2 | 130.84 (15) | C14—C13—C18 | 114.18 (16) |
C4—C3—C2 | 105.66 (15) | C13—C14—C15 | 111.31 (14) |
O3—C4—O1 | 119.04 (18) | C13—C14—H14A | 109.4 |
O3—C4—C3 | 132.9 (2) | C15—C14—H14A | 109.4 |
O1—C4—C3 | 107.95 (17) | C13—C14—H14B | 109.4 |
C3—C5—C7 | 122.69 (15) | C15—C14—H14B | 109.4 |
C3—C5—C6 | 122.35 (16) | H14A—C14—H14B | 108.0 |
C7—C5—C6 | 114.89 (15) | C16—C15—C14 | 111.38 (18) |
C5—C6—H6A | 109.5 | C16—C15—H15A | 109.4 |
C5—C6—H6B | 109.5 | C14—C15—H15A | 109.4 |
H6A—C6—H6B | 109.5 | C16—C15—H15B | 109.4 |
C5—C6—H6C | 109.5 | C14—C15—H15B | 109.4 |
H6A—C6—H6C | 109.5 | H15A—C15—H15B | 108.0 |
H6B—C6—H6C | 109.5 | C17—C16—C15 | 110.55 (17) |
C8—C7—C10 | 105.79 (15) | C17—C16—H16A | 109.5 |
C8—C7—C5 | 126.34 (16) | C15—C16—H16A | 109.5 |
C10—C7—C5 | 127.42 (16) | C17—C16—H16B | 109.5 |
C7—C8—O4 | 109.58 (14) | C15—C16—H16B | 109.5 |
C7—C8—C9 | 134.57 (16) | H16A—C16—H16B | 108.1 |
O4—C8—C9 | 115.78 (14) | C16—C17—C18 | 112.20 (17) |
C8—C9—H9A | 109.5 | C16—C17—H17A | 109.2 |
C8—C9—H9B | 109.5 | C18—C17—H17A | 109.2 |
H9A—C9—H9B | 109.5 | C16—C17—H17B | 109.2 |
C8—C9—H9C | 109.5 | C18—C17—H17B | 109.2 |
H9A—C9—H9C | 109.5 | H17A—C17—H17B | 107.9 |
H9B—C9—H9C | 109.5 | C13—C18—C17 | 113.23 (18) |
C11—C10—C7 | 108.02 (16) | C13—C18—H18A | 108.9 |
C11—C10—H10 | 126.0 | C17—C18—H18A | 108.9 |
C7—C10—H10 | 126.0 | C13—C18—H18B | 108.9 |
C10—C11—O4 | 109.24 (15) | C17—C18—H18B | 108.9 |
C10—C11—C12 | 135.47 (18) | H18A—C18—H18B | 107.7 |
C4—O1—C1—O2 | −175.07 (17) | C10—C7—C8—O4 | 0.56 (19) |
C4—O1—C1—C2 | 7.3 (2) | C5—C7—C8—O4 | 173.34 (15) |
O2—C1—C2—C13 | −25.2 (3) | C10—C7—C8—C9 | −176.35 (19) |
O1—C1—C2—C13 | 151.91 (17) | C5—C7—C8—C9 | −3.6 (3) |
O2—C1—C2—C3 | 167.9 (2) | C11—O4—C8—C7 | 0.10 (18) |
O1—C1—C2—C3 | −14.98 (18) | C11—O4—C8—C9 | 177.66 (15) |
C13—C2—C3—C5 | 43.2 (3) | C8—C7—C10—C11 | −1.0 (2) |
C1—C2—C3—C5 | −150.96 (18) | C5—C7—C10—C11 | −173.72 (16) |
C13—C2—C3—C4 | −149.22 (18) | C7—C10—C11—O4 | 1.1 (2) |
C1—C2—C3—C4 | 16.65 (18) | C7—C10—C11—C12 | 179.3 (2) |
C1—O1—C4—O3 | −179.44 (18) | C8—O4—C11—C10 | −0.78 (19) |
C1—O1—C4—C3 | 3.5 (2) | C8—O4—C11—C12 | −179.38 (16) |
C5—C3—C4—O3 | −20.3 (3) | C1—C2—C13—C14 | −161.83 (17) |
C2—C3—C4—O3 | 170.7 (2) | C3—C2—C13—C14 | 1.7 (3) |
C5—C3—C4—O1 | 156.12 (16) | C1—C2—C13—C18 | 17.0 (3) |
C2—C3—C4—O1 | −12.80 (18) | C3—C2—C13—C18 | −179.45 (17) |
C4—C3—C5—C7 | −155.36 (17) | C2—C13—C14—C15 | 129.21 (18) |
C2—C3—C5—C7 | 10.5 (3) | C18—C13—C14—C15 | −49.8 (2) |
C4—C3—C5—C6 | 21.5 (3) | C13—C14—C15—C16 | 55.6 (2) |
C2—C3—C5—C6 | −172.65 (17) | C14—C15—C16—C17 | −58.5 (2) |
C3—C5—C7—C8 | 46.0 (3) | C15—C16—C17—C18 | 54.9 (3) |
C6—C5—C7—C8 | −131.09 (19) | C2—C13—C18—C17 | −132.1 (2) |
C3—C5—C7—C10 | −142.76 (18) | C14—C13—C18—C17 | 46.9 (2) |
C6—C5—C7—C10 | 40.1 (2) | C16—C17—C18—C13 | −49.1 (3) |
Experimental details
(1E) | (2E) | (3E) | (4E) | |
Crystal data | ||||
Chemical formula | C15H16O4 | C16H18O4 | C17H18O4 | C18H20O4 |
Mr | 260.28 | 274.30 | 286.31 | 300.34 |
Crystal system, space group | Monoclinic, P21/n | Monoclinic, P21/n | Monoclinic, P21/n | Monoclinic, P21/n |
Temperature (K) | 173 | 173 | 173 | 173 |
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) |
V (Å3) | 1329.5 (15) | 1436.29 (18) | 1464.04 (13) | 1580.59 (19) |
Z | 4 | 4 | 4 | 4 |
Radiation type | Mo Kα | Mo Kα | Mo Kα | Mo Kα |
µ (mm−1) | 0.09 | 0.09 | 0.09 | 0.09 |
Crystal size (mm) | 0.18 × 0.10 × 0.10 | 0.13 × 0.09 × 0.03 | 0.29 × 0.19 × 0.11 | 0.31 × 0.17 × 0.07 |
Data collection | ||||
Diffractometer | Rigaku RAXIS-RAPID Imaging Plate diffractometer | Rigaku RAXIS-RAPID Imaging Plate diffractometer | Rigaku RAXIS-RAPID Imaging Plate diffractometer | Rigaku RAXIS-RAPID Imaging Plate diffractometer |
Absorption correction | Multi-scan ABSCOR (Higashi, 1995) | Multi-scan ABSCOR (Higashi, 1995) | Multi scan ABSCOR (Higashi, 1995) | Multi-scan ABSCOR (Higashi, 1995) |
Tmin, Tmax | 0.814, 0.942 | 0.886, 0.946 | 0.860, 0.968 | 0.872, 0.894 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 12492, 3032, 2258 | 13610, 3305, 1772 | 13814, 3340, 2764 | 15155, 3582, 1915 |
Rint | 0.023 | 0.052 | 0.027 | 0.047 |
(sin θ/λ)max (Å−1) | 0.649 | 0.649 | 0.648 | 0.647 |
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 reflections | 3032 | 3305 | 3340 | 3582 |
No. of parameters | 177 | 201 | 193 | 202 |
No. of restraints | 1 | 1 | 0 | 0 |
H-atom treatment | H-atom parameters constrained | H-atom parameters constrained | H-atom parameters constrained | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.34, −0.24 | 0.24, −0.24 | 0.35, −0.18 | 0.18, −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.