Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536804031587/fl6132sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536804031587/fl6132Isup2.hkl |
CCDC reference: 262435
Data collection: CAD-4 Diffractometer Control Software (Enraf-Nonius, 1993); cell refinement: CAD-4 Diffractometer Control Software; data reduction: CAD-4 Diffractometer Control Software; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2002) and ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: SHELXL97.
C13H14O4 | F(000) = 496 |
Mr = 234.24 | Dx = 1.331 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
a = 10.811 (2) Å | Cell parameters from 25 reflections |
b = 5.4155 (5) Å | θ = 10–15° |
c = 20.210 (5) Å | µ = 0.10 mm−1 |
β = 98.871 (1)° | T = 173 K |
V = 1169.1 (4) Å3 | Block, colourless |
Z = 4 | 0.30 × 0.30 × 0.30 mm |
Enraf-Nonius CAD-4 diffractometer | Rint = 0.061 |
Radiation source: fine-focus sealed tube | θmax = 22.5°, θmin = 3.0° |
Graphite monochromator | h = −11→11 |
ω/2θ scans | k = −5→5 |
2926 measured reflections | l = 0→21 |
1512 independent reflections | 3 standard reflections every 100 reflections |
1179 reflections with I > 2σ(I) | intensity decay: none |
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)] = 0.039 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.095 | H-atom parameters constrained |
S = 1.03 | w = 1/[σ2(Fo2) + (0.0441P)2 + 0.1845P] where P = (Fo2 + 2Fc2)/3 |
1512 reflections | (Δ/σ)max < 0.001 |
154 parameters | Δρmax = 0.14 e Å−3 |
0 restraints | Δρmin = −0.16 e Å−3 |
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes. |
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. |
x | y | z | Uiso*/Ueq | ||
C2 | 0.2058 (2) | 0.1333 (4) | 0.94864 (12) | 0.0249 (6) | |
C3 | 0.22732 (19) | 0.2678 (4) | 0.88466 (12) | 0.0235 (6) | |
H4 | 0.2212 | 0.4509 | 0.8898 | 0.028* | |
C4 | 0.1239 (2) | 0.1712 (4) | 0.83195 (13) | 0.0289 (6) | |
H3A | 0.0510 | 0.2839 | 0.8263 | 0.035* | |
H3B | 0.1537 | 0.1524 | 0.7883 | 0.035* | |
C5 | 0.0903 (2) | −0.0753 (4) | 0.85849 (12) | 0.0272 (6) | |
C6 | 0.3220 (2) | 0.0529 (5) | 0.99407 (12) | 0.0326 (6) | |
H6A | 0.3735 | 0.1978 | 1.0085 | 0.039* | |
H6B | 0.3696 | −0.0610 | 0.9700 | 0.039* | |
H6C | 0.2986 | −0.0304 | 1.0334 | 0.039* | |
C7 | 0.1174 (2) | 0.2820 (5) | 0.98468 (13) | 0.0377 (7) | |
H7A | 0.0371 | 0.3025 | 0.9553 | 0.045* | |
H7B | 0.1540 | 0.4446 | 0.9965 | 0.045* | |
H7C | 0.1041 | 0.1949 | 1.0255 | 0.045* | |
C8 | 0.4417 (2) | 0.3579 (4) | 0.87954 (12) | 0.0255 (6) | |
C9 | 0.55343 (19) | 0.2788 (4) | 0.85110 (11) | 0.0223 (5) | |
C10 | 0.6580 (2) | 0.4322 (4) | 0.86110 (12) | 0.0277 (6) | |
H10 | 0.6567 | 0.5786 | 0.8869 | 0.033* | |
C11 | 0.7632 (2) | 0.3729 (5) | 0.83383 (13) | 0.0342 (6) | |
H11 | 0.8341 | 0.4789 | 0.8405 | 0.041* | |
C12 | 0.7658 (2) | 0.1598 (5) | 0.79682 (13) | 0.0330 (6) | |
H12 | 0.8382 | 0.1198 | 0.7777 | 0.040* | |
C13 | 0.6629 (2) | 0.0040 (5) | 0.78747 (12) | 0.0294 (6) | |
H13 | 0.6654 | −0.1441 | 0.7625 | 0.035* | |
C14 | 0.5569 (2) | 0.0633 (4) | 0.81435 (11) | 0.0264 (6) | |
H14 | 0.4864 | −0.0434 | 0.8077 | 0.032* | |
O1 | 0.13867 (14) | −0.0946 (3) | 0.92346 (8) | 0.0285 (4) | |
O2 | 0.02914 (15) | −0.2384 (3) | 0.82908 (9) | 0.0389 (5) | |
O3 | 0.34472 (13) | 0.1986 (3) | 0.86410 (8) | 0.0256 (4) | |
O4 | 0.43509 (15) | 0.5420 (3) | 0.91170 (9) | 0.0431 (5) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C2 | 0.0242 (12) | 0.0211 (13) | 0.0298 (14) | −0.0019 (10) | 0.0058 (10) | −0.0039 (11) |
C3 | 0.0187 (12) | 0.0206 (12) | 0.0323 (14) | 0.0031 (10) | 0.0070 (10) | 0.0002 (11) |
C4 | 0.0228 (13) | 0.0282 (14) | 0.0346 (14) | −0.0005 (10) | 0.0006 (11) | 0.0029 (12) |
C5 | 0.0193 (12) | 0.0275 (14) | 0.0352 (15) | 0.0007 (11) | 0.0051 (11) | −0.0022 (13) |
C6 | 0.0342 (14) | 0.0332 (15) | 0.0294 (14) | 0.0003 (12) | 0.0014 (11) | 0.0000 (12) |
C7 | 0.0353 (14) | 0.0390 (16) | 0.0416 (16) | −0.0013 (12) | 0.0147 (13) | −0.0063 (13) |
C8 | 0.0242 (13) | 0.0230 (13) | 0.0288 (14) | −0.0031 (11) | 0.0025 (10) | −0.0012 (12) |
C9 | 0.0223 (13) | 0.0223 (13) | 0.0218 (12) | −0.0003 (10) | 0.0019 (10) | 0.0027 (11) |
C10 | 0.0259 (13) | 0.0259 (13) | 0.0306 (14) | −0.0013 (11) | 0.0023 (10) | −0.0020 (11) |
C11 | 0.0241 (13) | 0.0380 (16) | 0.0406 (16) | −0.0059 (12) | 0.0055 (11) | 0.0016 (13) |
C12 | 0.0232 (13) | 0.0402 (16) | 0.0365 (15) | 0.0056 (12) | 0.0073 (11) | −0.0006 (13) |
C13 | 0.0270 (14) | 0.0301 (14) | 0.0304 (14) | 0.0031 (11) | 0.0030 (11) | −0.0036 (11) |
C14 | 0.0241 (13) | 0.0244 (14) | 0.0303 (14) | −0.0015 (11) | 0.0031 (11) | 0.0003 (11) |
O1 | 0.0316 (9) | 0.0222 (9) | 0.0317 (10) | −0.0054 (7) | 0.0044 (7) | 0.0012 (8) |
O2 | 0.0315 (10) | 0.0307 (10) | 0.0519 (12) | −0.0060 (8) | −0.0022 (9) | −0.0062 (9) |
O3 | 0.0197 (8) | 0.0233 (9) | 0.0347 (10) | −0.0041 (7) | 0.0073 (7) | −0.0044 (8) |
O4 | 0.0315 (10) | 0.0364 (11) | 0.0642 (13) | −0.0098 (8) | 0.0168 (9) | −0.0260 (11) |
C2—O1 | 1.482 (3) | C7—H7B | 0.9800 |
C2—C6 | 1.502 (3) | C7—H7C | 0.9800 |
C2—C7 | 1.519 (3) | C8—O4 | 1.198 (3) |
C2—C3 | 1.533 (3) | C8—O3 | 1.356 (3) |
C3—O3 | 1.445 (3) | C8—C9 | 1.479 (3) |
C3—C4 | 1.514 (3) | C9—C14 | 1.387 (3) |
C3—H4 | 1.0000 | C9—C10 | 1.392 (3) |
C4—C5 | 1.504 (3) | C10—C11 | 1.376 (3) |
C4—H3A | 0.9900 | C10—H10 | 0.9500 |
C4—H3B | 0.9900 | C11—C12 | 1.378 (3) |
C5—O2 | 1.204 (3) | C11—H11 | 0.9500 |
C5—O1 | 1.340 (3) | C12—C13 | 1.385 (3) |
C6—H6A | 0.9800 | C12—H12 | 0.9500 |
C6—H6B | 0.9800 | C13—C14 | 1.380 (3) |
C6—H6C | 0.9800 | C13—H13 | 0.9500 |
C7—H7A | 0.9800 | C14—H14 | 0.9500 |
O1—C2—C6 | 106.72 (18) | C2—C7—H7B | 109.5 |
O1—C2—C7 | 107.19 (18) | H7A—C7—H7B | 109.5 |
C6—C2—C7 | 112.9 (2) | C2—C7—H7C | 109.5 |
O1—C2—C3 | 103.66 (17) | H7A—C7—H7C | 109.5 |
C6—C2—C3 | 115.59 (19) | H7B—C7—H7C | 109.5 |
C7—C2—C3 | 109.96 (19) | O4—C8—O3 | 123.1 (2) |
O3—C3—C4 | 107.11 (18) | O4—C8—C9 | 124.9 (2) |
O3—C3—C2 | 111.96 (17) | O3—C8—C9 | 112.0 (2) |
C4—C3—C2 | 103.74 (18) | C14—C9—C10 | 119.4 (2) |
O3—C3—H4 | 111.2 | C14—C9—C8 | 122.9 (2) |
C4—C3—H4 | 111.2 | C10—C9—C8 | 117.7 (2) |
C2—C3—H4 | 111.2 | C11—C10—C9 | 120.4 (2) |
C5—C4—C3 | 104.41 (19) | C11—C10—H10 | 119.8 |
C5—C4—H3A | 110.9 | C9—C10—H10 | 119.8 |
C3—C4—H3A | 110.9 | C10—C11—C12 | 120.0 (2) |
C5—C4—H3B | 110.9 | C10—C11—H11 | 120.0 |
C3—C4—H3B | 110.9 | C12—C11—H11 | 120.0 |
H3A—C4—H3B | 108.9 | C11—C12—C13 | 120.1 (2) |
O2—C5—O1 | 121.9 (2) | C11—C12—H12 | 119.9 |
O2—C5—C4 | 128.3 (2) | C13—C12—H12 | 119.9 |
O1—C5—C4 | 109.8 (2) | C14—C13—C12 | 120.1 (2) |
C2—C6—H6A | 109.5 | C14—C13—H13 | 119.9 |
C2—C6—H6B | 109.5 | C12—C13—H13 | 119.9 |
H6A—C6—H6B | 109.5 | C13—C14—C9 | 120.0 (2) |
C2—C6—H6C | 109.5 | C13—C14—H14 | 120.0 |
H6A—C6—H6C | 109.5 | C9—C14—H14 | 120.0 |
H6B—C6—H6C | 109.5 | C5—O1—C2 | 111.60 (17) |
C2—C7—H7A | 109.5 | C8—O3—C3 | 116.81 (18) |
O1—C2—C3—O3 | −90.1 (2) | C9—C10—C11—C12 | −0.5 (4) |
C6—C2—C3—O3 | 26.3 (3) | C10—C11—C12—C13 | −0.5 (4) |
C7—C2—C3—O3 | 155.54 (19) | C11—C12—C13—C14 | 1.0 (4) |
O1—C2—C3—C4 | 25.0 (2) | C12—C13—C14—C9 | −0.3 (4) |
C6—C2—C3—C4 | 141.4 (2) | C10—C9—C14—C13 | −0.7 (3) |
C7—C2—C3—C4 | −89.3 (2) | C8—C9—C14—C13 | 178.0 (2) |
O3—C3—C4—C5 | 94.4 (2) | O2—C5—O1—C2 | −177.8 (2) |
C2—C3—C4—C5 | −24.2 (2) | C4—C5—O1—C2 | 1.7 (2) |
C3—C4—C5—O2 | −165.7 (2) | C6—C2—O1—C5 | −139.67 (19) |
C3—C4—C5—O1 | 14.8 (2) | C7—C2—O1—C5 | 99.1 (2) |
O4—C8—C9—C14 | 179.7 (2) | C3—C2—O1—C5 | −17.2 (2) |
O3—C8—C9—C14 | −1.3 (3) | O4—C8—O3—C3 | 3.9 (3) |
O4—C8—C9—C10 | −1.5 (4) | C9—C8—O3—C3 | −175.10 (17) |
O3—C8—C9—C10 | 177.5 (2) | C4—C3—O3—C8 | 146.34 (19) |
C14—C9—C10—C11 | 1.1 (3) | C2—C3—O3—C8 | −100.6 (2) |
C8—C9—C10—C11 | −177.7 (2) |