Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807003194/bh2073sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807003194/bh2073Isup2.hkl |
CCDC reference: 636849
Key indicators
- Single-crystal X-ray study
- T = 298 K
- Mean (C-C) = 0.003 Å
- R factor = 0.044
- wR factor = 0.125
- Data-to-parameter ratio = 12.7
checkCIF/PLATON results
No syntax errors found
Alert level B PLAT148_ALERT_3_B su on the b - Axis is Too Large (x 1000) . 10 Ang.
0 ALERT level A = In general: serious problem 1 ALERT level B = Potentially serious problem 0 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 0 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 1 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
Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1994); cell refinement: CAD-4 EXPRESS; data reduction: XCAD4 (Harms & Wocadlo, 1995); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: X-SEED (Barbour, 2001) and ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).
C18H16O3 | Z = 2 |
Mr = 280.31 | F(000) = 296 |
Triclinic, P1 | Dx = 1.358 Mg m−3 |
Hall symbol: -P 1 | Melting point = 425–427 K |
a = 6.6380 (13) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 7.911 (10) Å | Cell parameters from 25 reflections |
c = 13.498 (5) Å | θ = 9.8–15.7° |
α = 81.24 (5)° | µ = 0.09 mm−1 |
β = 80.21 (2)° | T = 298 K |
γ = 82.05 (4)° | Plate, colourless |
V = 685.7 (9) Å3 | 0.55 × 0.45 × 0.10 mm |
Enraf–Nonius TurboCAD-4 diffractometer | Rint = 0.019 |
Radiation source: fine-focus sealed tube | θmax = 25.1°, θmin = 1.5° |
Graphite monochromator | h = −7→7 |
non–profiled ω/2θ scans | k = −9→9 |
2750 measured reflections | l = −1→16 |
2413 independent reflections | 3 standard reflections every 60 min |
1932 reflections with I > 2σ(I) | intensity decay: 1% |
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)] = 0.044 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.125 | H-atom parameters constrained |
S = 1.06 | w = 1/[σ2(Fo2) + (0.0716P)2 + 0.1555P] where P = (Fo2 + 2Fc2)/3 |
2413 reflections | (Δ/σ)max < 0.001 |
190 parameters | Δρmax = 0.24 e Å−3 |
0 restraints | Δρmin = −0.19 e Å−3 |
Experimental. Spectroscopic analysis: 1H NMR (300 MHz, CDCl3, δ, p.p.m.): 2.48 (2H, m), 4.53 (1H, dd, J 9.6, 4.2 Hz), 4.71 (2H, m), 5.95 (2H, s), 6.25 (1H, m), 6.80 (1H, d, J 7.8 Hz), 6.88 (1H, dd, J 7.8, 1.8 Hz), 6.94 (1H, d, J 1.8 Hz), 2.26–7.36 (5H, m); 13C NMR (75 MHz, CDCl3, δ, p.p.m.): 33.3, 68.1, 75.7, 101.2, 106.9, 108.4, 119.7, 121.6, 125.1, 127.8, 128.8, 136.2, 136.4, 138.3, 147.2, 148.0; IR: 1659, 1589, 1489, 1253, 1027, 1018, 777 cm-1. |
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. Least-squares planes (x,y,z in crystal coordinates) and deviations from them (* indicates atom used to define plane) 3.9500 (0.0064) x + 6.4392 (0.0087) y + 6.8342 (0.0120) z = 6.3962 (0.0092) * 0.0022 (0.0012) C6 * -0.0006 (0.0013) C7 * -0.0011 (0.0014) C8 * 0.0013 (0.0013) C9 * 0.0004 (0.0013) C10 * -0.0021 (0.0012) C11 - 0.0449 (0.0028) C2 Rms deviation of fitted atoms = 0.0015 1.7907 (0.0066) x + 7.7170 (0.0096) y + 4.5601 (0.0110) z = 6.6670 (0.0084) Angle to previous plane (with approximate e.s.d.) = 23.79 (0.11) * -0.0757 (0.0009) C1 * 0.0516 (0.0012) C2 * 0.0354 (0.0012) C3 * -0.1025 (0.0012) C4 * 0.0911 (0.0010) C5 - 0.6124 (0.0023) O1 0.1831 (0.0027) C6 Rms deviation of fitted atoms = 0.0754 - 3.7458 (0.0061) x + 5.8458 (0.0082) y - 0.2828 (0.0099) z = 3.7265 (0.0060) Angle to previous plane (with approximate e.s.d.) = 51.43 (0.09) * 0.0032 (0.0012) C12 * -0.0086 (0.0012) C13 * 0.0065 (0.0012) C14 * 0.0011 (0.0013) C15 * -0.0065 (0.0014) C16 * 0.0042 (0.0013) C17 0.0353 (0.0027) C5 0.2559 (0.0029) O1 - 0.0026 (0.0026) O2 0.1730 (0.0033) C18 Rms deviation of fitted atoms = 0.0056 |
x | y | z | Uiso*/Ueq | ||
O1 | 0.12451 (18) | 0.76062 (18) | −0.00835 (9) | 0.0472 (4) | |
O2 | −0.3421 (2) | 0.43061 (19) | 0.26385 (10) | 0.0561 (4) | |
O3 | −0.2820 (2) | 0.47454 (18) | 0.42096 (9) | 0.0501 (4) | |
C1 | 0.2124 (3) | 0.8621 (3) | −0.09679 (13) | 0.0433 (4) | |
H1A | 0.1673 | 0.9826 | −0.0911 | 0.052* | |
H1B | 0.1623 | 0.8341 | −0.1551 | 0.052* | |
C2 | 0.4443 (2) | 0.8350 (2) | −0.11424 (12) | 0.0330 (4) | |
C3 | 0.5435 (3) | 0.7648 (2) | −0.03782 (13) | 0.0389 (4) | |
H3 | 0.6865 | 0.7487 | −0.0497 | 0.047* | |
C4 | 0.4361 (3) | 0.7101 (2) | 0.06656 (13) | 0.0390 (4) | |
H4A | 0.5010 | 0.7514 | 0.1160 | 0.047* | |
H4B | 0.4487 | 0.5854 | 0.0797 | 0.047* | |
C5 | 0.2089 (3) | 0.7812 (2) | 0.07803 (13) | 0.0374 (4) | |
H5 | 0.1986 | 0.9047 | 0.0824 | 0.045* | |
C6 | 0.5468 (2) | 0.8896 (2) | −0.21797 (12) | 0.0329 (4) | |
C7 | 0.7398 (3) | 0.8116 (2) | −0.25646 (14) | 0.0441 (4) | |
H7 | 0.8083 | 0.7255 | −0.2152 | 0.053* | |
C8 | 0.8311 (3) | 0.8596 (3) | −0.35456 (15) | 0.0511 (5) | |
H8 | 0.9599 | 0.8059 | −0.3786 | 0.061* | |
C9 | 0.7324 (3) | 0.9872 (2) | −0.41739 (14) | 0.0471 (5) | |
H9 | 0.7942 | 1.0198 | −0.4835 | 0.057* | |
C10 | 0.5415 (3) | 1.0654 (2) | −0.38087 (13) | 0.0424 (4) | |
H10 | 0.4742 | 1.1513 | −0.4227 | 0.051* | |
C11 | 0.4492 (3) | 1.0180 (2) | −0.28316 (13) | 0.0372 (4) | |
H11 | 0.3199 | 1.0720 | −0.2600 | 0.045* | |
C12 | 0.0809 (2) | 0.6982 (2) | 0.17137 (13) | 0.0347 (4) | |
C13 | −0.0727 (3) | 0.5973 (2) | 0.16350 (12) | 0.0358 (4) | |
H13 | −0.0968 | 0.5759 | 0.1009 | 0.043* | |
C14 | −0.1849 (3) | 0.5323 (2) | 0.25207 (13) | 0.0351 (4) | |
C15 | −0.1496 (3) | 0.5585 (2) | 0.34539 (12) | 0.0364 (4) | |
C16 | 0.0009 (3) | 0.6542 (3) | 0.35537 (14) | 0.0470 (5) | |
H16 | 0.0259 | 0.6712 | 0.4187 | 0.056* | |
C17 | 0.1148 (3) | 0.7246 (3) | 0.26592 (14) | 0.0455 (5) | |
H17 | 0.2170 | 0.7916 | 0.2699 | 0.055* | |
C18 | −0.4219 (3) | 0.4145 (3) | 0.36833 (14) | 0.0529 (5) | |
H18A | −0.4387 | 0.2950 | 0.3938 | 0.063* | |
H18B | −0.5555 | 0.4820 | 0.3790 | 0.063* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0376 (7) | 0.0680 (9) | 0.0360 (7) | −0.0203 (6) | −0.0051 (5) | 0.0057 (6) |
O2 | 0.0633 (9) | 0.0691 (9) | 0.0419 (8) | −0.0418 (8) | −0.0004 (6) | −0.0042 (6) |
O3 | 0.0517 (8) | 0.0635 (9) | 0.0346 (7) | −0.0245 (6) | 0.0012 (6) | 0.0023 (6) |
C1 | 0.0336 (9) | 0.0572 (11) | 0.0338 (9) | −0.0041 (8) | −0.0020 (7) | 0.0061 (8) |
C2 | 0.0322 (8) | 0.0272 (8) | 0.0384 (9) | −0.0047 (6) | −0.0019 (7) | −0.0037 (6) |
C3 | 0.0295 (8) | 0.0406 (10) | 0.0440 (10) | −0.0031 (7) | −0.0030 (7) | −0.0014 (8) |
C4 | 0.0349 (9) | 0.0416 (9) | 0.0385 (9) | −0.0037 (7) | −0.0061 (7) | 0.0013 (7) |
C5 | 0.0354 (9) | 0.0385 (9) | 0.0378 (9) | −0.0086 (7) | −0.0047 (7) | −0.0005 (7) |
C6 | 0.0327 (8) | 0.0291 (8) | 0.0375 (9) | −0.0091 (6) | −0.0028 (7) | −0.0040 (7) |
C7 | 0.0395 (10) | 0.0390 (10) | 0.0475 (10) | −0.0021 (8) | 0.0013 (8) | 0.0026 (8) |
C8 | 0.0405 (10) | 0.0524 (12) | 0.0536 (12) | −0.0038 (9) | 0.0089 (9) | −0.0046 (9) |
C9 | 0.0508 (11) | 0.0517 (11) | 0.0373 (10) | −0.0189 (9) | 0.0053 (8) | −0.0026 (8) |
C10 | 0.0483 (10) | 0.0418 (10) | 0.0375 (9) | −0.0112 (8) | −0.0091 (8) | 0.0017 (8) |
C11 | 0.0349 (9) | 0.0366 (9) | 0.0394 (9) | −0.0054 (7) | −0.0037 (7) | −0.0044 (7) |
C12 | 0.0309 (8) | 0.0338 (9) | 0.0376 (9) | −0.0049 (7) | −0.0042 (7) | 0.0002 (7) |
C13 | 0.0368 (9) | 0.0393 (9) | 0.0320 (9) | −0.0069 (7) | −0.0050 (7) | −0.0046 (7) |
C14 | 0.0345 (8) | 0.0321 (8) | 0.0387 (9) | −0.0088 (7) | −0.0044 (7) | −0.0016 (7) |
C15 | 0.0382 (9) | 0.0360 (9) | 0.0326 (9) | −0.0064 (7) | −0.0004 (7) | −0.0005 (7) |
C16 | 0.0515 (11) | 0.0578 (12) | 0.0355 (10) | −0.0185 (9) | −0.0074 (8) | −0.0061 (8) |
C17 | 0.0448 (10) | 0.0525 (11) | 0.0430 (10) | −0.0210 (9) | −0.0069 (8) | −0.0044 (8) |
C18 | 0.0541 (11) | 0.0632 (12) | 0.0423 (11) | −0.0271 (10) | 0.0014 (9) | −0.0011 (9) |
O1—C5 | 1.416 (2) | C7—C8 | 1.379 (3) |
O1—C1 | 1.418 (2) | C7—H7 | 0.9300 |
O2—C14 | 1.377 (2) | C8—C9 | 1.383 (3) |
O2—C18 | 1.413 (2) | C8—H8 | 0.9300 |
O3—C15 | 1.380 (2) | C9—C10 | 1.377 (3) |
O3—C18 | 1.429 (2) | C9—H9 | 0.9300 |
C1—C2 | 1.508 (2) | C10—C11 | 1.376 (2) |
C1—H1A | 0.9700 | C10—H10 | 0.9300 |
C1—H1B | 0.9700 | C11—H11 | 0.9300 |
C2—C3 | 1.327 (2) | C12—C17 | 1.384 (3) |
C2—C6 | 1.477 (2) | C12—C13 | 1.405 (2) |
C3—C4 | 1.496 (2) | C13—C14 | 1.365 (2) |
C3—H3 | 0.9300 | C13—H13 | 0.9300 |
C4—C5 | 1.525 (2) | C14—C15 | 1.370 (2) |
C4—H4A | 0.9700 | C15—C16 | 1.369 (3) |
C4—H4B | 0.9700 | C16—C17 | 1.393 (3) |
C5—C12 | 1.509 (2) | C16—H16 | 0.9300 |
C5—H5 | 0.9800 | C17—H17 | 0.9300 |
C6—C7 | 1.395 (2) | C18—H18A | 0.9700 |
C6—C11 | 1.402 (3) | C18—H18B | 0.9700 |
C5—O1—C1 | 111.78 (14) | C9—C8—H8 | 119.8 |
C14—O2—C18 | 105.40 (14) | C10—C9—C8 | 119.15 (17) |
C15—O3—C18 | 104.49 (13) | C10—C9—H9 | 120.4 |
O1—C1—C2 | 113.01 (14) | C8—C9—H9 | 120.4 |
O1—C1—H1A | 109.0 | C11—C10—C9 | 120.73 (17) |
C2—C1—H1A | 109.0 | C11—C10—H10 | 119.6 |
O1—C1—H1B | 109.0 | C9—C10—H10 | 119.6 |
C2—C1—H1B | 109.0 | C10—C11—C6 | 121.10 (16) |
H1A—C1—H1B | 107.8 | C10—C11—H11 | 119.4 |
C3—C2—C6 | 124.15 (15) | C6—C11—H11 | 119.4 |
C3—C2—C1 | 119.37 (15) | C17—C12—C13 | 119.90 (16) |
C6—C2—C1 | 116.48 (14) | C17—C12—C5 | 118.96 (15) |
C2—C3—C4 | 123.14 (16) | C13—C12—C5 | 121.13 (15) |
C2—C3—H3 | 118.4 | C14—C13—C12 | 116.84 (16) |
C4—C3—H3 | 118.4 | C14—C13—H13 | 121.6 |
C3—C4—C5 | 110.94 (14) | C12—C13—H13 | 121.6 |
C3—C4—H4A | 109.5 | C13—C14—C15 | 122.82 (16) |
C5—C4—H4A | 109.5 | C13—C14—O2 | 127.56 (16) |
C3—C4—H4B | 109.5 | C15—C14—O2 | 109.60 (15) |
C5—C4—H4B | 109.5 | C16—C15—C14 | 121.57 (16) |
H4A—C4—H4B | 108.0 | C16—C15—O3 | 128.26 (16) |
O1—C5—C12 | 108.62 (14) | C14—C15—O3 | 110.16 (15) |
O1—C5—C4 | 110.16 (14) | C15—C16—C17 | 116.61 (17) |
C12—C5—C4 | 113.69 (14) | C15—C16—H16 | 121.7 |
O1—C5—H5 | 108.1 | C17—C16—H16 | 121.7 |
C12—C5—H5 | 108.1 | C12—C17—C16 | 122.24 (17) |
C4—C5—H5 | 108.1 | C12—C17—H17 | 118.9 |
C7—C6—C11 | 117.30 (16) | C16—C17—H17 | 118.9 |
C7—C6—C2 | 121.72 (15) | O2—C18—O3 | 108.62 (15) |
C11—C6—C2 | 120.93 (15) | O2—C18—H18A | 110.0 |
C8—C7—C6 | 121.23 (17) | O3—C18—H18A | 110.0 |
C8—C7—H7 | 119.4 | O2—C18—H18B | 110.0 |
C6—C7—H7 | 119.4 | O3—C18—H18B | 110.0 |
C7—C8—C9 | 120.49 (18) | H18A—C18—H18B | 108.3 |
C7—C8—H8 | 119.8 | ||
C5—O1—C1—C2 | 52.1 (2) | C4—C5—C12—C17 | 66.7 (2) |
O1—C1—C2—C3 | −18.6 (2) | O1—C5—C12—C13 | 8.9 (2) |
O1—C1—C2—C6 | 161.16 (15) | C4—C5—C12—C13 | −114.15 (19) |
C6—C2—C3—C4 | −179.84 (16) | C17—C12—C13—C14 | 1.2 (2) |
C1—C2—C3—C4 | −0.1 (3) | C5—C12—C13—C14 | −177.91 (15) |
C2—C3—C4—C5 | −12.5 (2) | C12—C13—C14—C15 | −1.5 (3) |
C1—O1—C5—C12 | 169.10 (13) | C12—C13—C14—O2 | −179.89 (16) |
C1—O1—C5—C4 | −65.77 (19) | C18—O2—C14—C13 | −173.58 (18) |
C3—C4—C5—O1 | 44.0 (2) | C18—O2—C14—C15 | 7.9 (2) |
C3—C4—C5—C12 | 166.21 (15) | C13—C14—C15—C16 | 0.7 (3) |
C3—C2—C6—C7 | 27.5 (3) | O2—C14—C15—C16 | 179.28 (16) |
C1—C2—C6—C7 | −152.24 (17) | C13—C14—C15—O3 | −178.46 (15) |
C3—C2—C6—C11 | −155.07 (17) | O2—C14—C15—O3 | 0.2 (2) |
C1—C2—C6—C11 | 25.2 (2) | C18—O3—C15—C16 | 172.9 (2) |
C11—C6—C7—C8 | 0.3 (3) | C18—O3—C15—C14 | −8.0 (2) |
C2—C6—C7—C8 | 177.82 (17) | C14—C15—C16—C17 | 0.6 (3) |
C6—C7—C8—C9 | 0.0 (3) | O3—C15—C16—C17 | 179.53 (17) |
C7—C8—C9—C10 | −0.2 (3) | C13—C12—C17—C16 | 0.0 (3) |
C8—C9—C10—C11 | 0.0 (3) | C5—C12—C17—C16 | 179.13 (17) |
C9—C10—C11—C6 | 0.3 (3) | C15—C16—C17—C12 | −0.9 (3) |
C7—C6—C11—C10 | −0.5 (2) | C14—O2—C18—O3 | −12.9 (2) |
C2—C6—C11—C10 | −177.99 (16) | C15—O3—C18—O2 | 12.9 (2) |
O1—C5—C12—C17 | −170.23 (16) |