Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805003776/su6164sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536805003776/su6164Isup2.hkl |
CCDC reference: 269867
Key indicators
- Single-crystal X-ray study
- T = 296 K
- Mean (C-C) = 0.004 Å
- R factor = 0.038
- wR factor = 0.098
- Data-to-parameter ratio = 8.5
checkCIF/PLATON results
No syntax errors found
Alert level G REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is correct. If it is not, please give the correct count in the _publ_section_exptl_refinement section of the submitted CIF. From the CIF: _diffrn_reflns_theta_max 69.89 From the CIF: _reflns_number_total 1722 Count of symmetry unique reflns 1721 Completeness (_total/calc) 100.06% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 1 Fraction of Friedel pairs measured 0.001 Are heavy atom types Z>Si present no
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 0 ALERT level C = Check and explain 1 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 0 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion
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, 1997a); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997b); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX publication routines (Farrugia, 1999).
C19H18O3 | F(000) = 624 |
Mr = 294.33 | Dx = 1.25 Mg m−3 |
Orthorhombic, P212121 | Cu Kα radiation, λ = 1.54178 Å |
Hall symbol: P 2ac 2ab | Cell parameters from 22 reflections |
a = 6.746 (1) Å | θ = 9.6–23.6° |
b = 12.605 (4) Å | µ = 0.68 mm−1 |
c = 18.320 (3) Å | T = 296 K |
V = 1557.8 (6) Å3 | Prism, colourless |
Z = 4 | 0.5 × 0.1 × 0.1 mm |
Enraf–Nonius CAD-4 diffractometer | Rint = 0.072 |
Radiation source: normal-focus sealed tube | θmax = 69.9°, θmin = 4.3° |
Graphite monochromator | h = −8→8 |
non–profiled ω/2θ scans | k = 0→15 |
3231 measured reflections | l = 0→22 |
1722 independent reflections | 3 standard reflections every 73 reflections |
1346 reflections with I > 2σ(I) | intensity decay: 4% |
Refinement on F2 | H-atom parameters constrained |
Least-squares matrix: full | w = 1/[σ2(Fo2) + (0.052P)2 + 0.0081P] where P = (Fo2 + 2Fc2)/3 |
R[F2 > 2σ(F2)] = 0.038 | (Δ/σ)max < 0.001 |
wR(F2) = 0.098 | Δρmax = 0.16 e Å−3 |
S = 1.05 | Δρmin = −0.16 e Å−3 |
1722 reflections | Extinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
203 parameters | Extinction coefficient: 0.0022 (6) |
0 restraints |
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 | ||
O3 | 0.9930 (3) | 0.80028 (12) | 0.08473 (10) | 0.0514 (5) | |
O2 | 1.1929 (3) | 0.72291 (14) | 0.20023 (10) | 0.0559 (5) | |
C15 | 0.9720 (4) | 0.69387 (16) | 0.09928 (12) | 0.0399 (5) | |
C14 | 1.0838 (4) | 0.65578 (18) | 0.15681 (12) | 0.0407 (5) | |
O1 | 1.1887 (3) | 0.51775 (13) | 0.23173 (10) | 0.0583 (5) | |
C9 | 0.7080 (4) | 0.42646 (17) | −0.03291 (14) | 0.0418 (5) | |
C13 | 1.0704 (4) | 0.54863 (19) | 0.17542 (13) | 0.0433 (6) | |
C11 | 0.8311 (4) | 0.52062 (17) | 0.08090 (12) | 0.0425 (5) | |
C16 | 0.8479 (4) | 0.62720 (18) | 0.06015 (13) | 0.0428 (6) | |
H16 | 0.7766 | 0.653 | 0.0205 | 0.051* | |
C12 | 0.9422 (4) | 0.48290 (18) | 0.13849 (13) | 0.0463 (6) | |
H12 | 0.9303 | 0.4123 | 0.1525 | 0.056* | |
C1 | 0.6858 (4) | 0.45215 (16) | 0.04198 (13) | 0.0437 (6) | |
C7 | 0.8976 (6) | 0.4256 (2) | −0.14535 (16) | 0.0686 (8) | |
H7 | 1.013 | 0.4417 | −0.1709 | 0.082* | |
C3 | 0.3724 (5) | 0.3583 (2) | 0.0422 (2) | 0.0679 (9) | |
H3 | 0.2624 | 0.3348 | 0.0682 | 0.081* | |
C2 | 0.5215 (5) | 0.4167 (2) | 0.07811 (17) | 0.0598 (7) | |
H2 | 0.5077 | 0.4314 | 0.1276 | 0.072* | |
C4 | 0.3879 (4) | 0.3363 (2) | −0.02890 (19) | 0.0629 (8) | |
H4 | 0.2876 | 0.2985 | −0.052 | 0.076* | |
C10 | 0.5545 (4) | 0.36963 (18) | −0.06943 (16) | 0.0505 (7) | |
C6 | 0.7405 (6) | 0.3741 (3) | −0.18079 (18) | 0.0725 (9) | |
H6 | 0.7507 | 0.3584 | −0.2302 | 0.087* | |
C19 | 0.8498 (5) | 0.84795 (19) | 0.03828 (16) | 0.0579 (7) | |
H19A | 0.8697 | 0.8239 | −0.0109 | 0.087* | |
H19B | 0.8637 | 0.9237 | 0.0401 | 0.087* | |
H19C | 0.7192 | 0.8285 | 0.0542 | 0.087* | |
C8 | 0.8811 (5) | 0.4523 (2) | −0.07317 (15) | 0.0544 (6) | |
H8 | 0.9846 | 0.4879 | −0.0502 | 0.065* | |
C17 | 1.1475 (6) | 0.4172 (2) | 0.26410 (19) | 0.0814 (11) | |
H17A | 1.0082 | 0.4119 | 0.2742 | 0.122* | |
H17B | 1.2209 | 0.4104 | 0.3087 | 0.122* | |
H17C | 1.1856 | 0.3617 | 0.2311 | 0.122* | |
C5 | 0.5752 (5) | 0.3472 (2) | −0.14412 (17) | 0.0647 (8) | |
H5 | 0.4728 | 0.313 | −0.1687 | 0.078* | |
C18 | 1.3839 (6) | 0.7457 (4) | 0.1759 (2) | 0.0950 (13) | |
H18A | 1.4505 | 0.6808 | 0.1635 | 0.142* | |
H18B | 1.4559 | 0.7813 | 0.2139 | 0.142* | |
H18C | 1.3769 | 0.7905 | 0.1337 | 0.142* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O3 | 0.0610 (11) | 0.0316 (8) | 0.0617 (11) | −0.0114 (8) | −0.0116 (10) | 0.0056 (7) |
O2 | 0.0638 (12) | 0.0502 (10) | 0.0537 (11) | −0.0136 (10) | −0.0059 (10) | −0.0061 (8) |
C15 | 0.0471 (14) | 0.0300 (10) | 0.0427 (12) | −0.0048 (10) | 0.0064 (11) | −0.0001 (9) |
C14 | 0.0445 (13) | 0.0378 (11) | 0.0397 (11) | −0.0067 (10) | 0.0028 (11) | −0.0046 (10) |
O1 | 0.0708 (13) | 0.0473 (9) | 0.0567 (10) | −0.0059 (10) | −0.0142 (10) | 0.0112 (8) |
C9 | 0.0428 (12) | 0.0271 (10) | 0.0554 (13) | 0.0023 (9) | −0.0053 (11) | 0.0017 (10) |
C13 | 0.0456 (13) | 0.0402 (12) | 0.0441 (12) | −0.0002 (11) | −0.0028 (11) | 0.0027 (10) |
C11 | 0.0434 (13) | 0.0356 (11) | 0.0485 (13) | −0.0050 (10) | 0.0029 (12) | −0.0025 (10) |
C16 | 0.0448 (13) | 0.0360 (11) | 0.0475 (13) | −0.0038 (10) | −0.0029 (11) | 0.0011 (9) |
C12 | 0.0507 (14) | 0.0329 (11) | 0.0555 (14) | −0.0017 (11) | −0.0002 (12) | 0.0015 (10) |
C1 | 0.0445 (13) | 0.0289 (10) | 0.0577 (14) | −0.0023 (10) | −0.0016 (12) | 0.0011 (10) |
C7 | 0.076 (2) | 0.0671 (18) | 0.0628 (18) | −0.0023 (17) | 0.0082 (17) | −0.0017 (14) |
C3 | 0.0509 (16) | 0.0480 (15) | 0.105 (3) | −0.0190 (13) | 0.0130 (17) | −0.0028 (16) |
C2 | 0.0618 (17) | 0.0461 (14) | 0.0716 (17) | −0.0112 (14) | 0.0096 (15) | −0.0020 (13) |
C4 | 0.0485 (15) | 0.0400 (14) | 0.100 (2) | −0.0075 (12) | −0.0132 (17) | −0.0089 (15) |
C10 | 0.0517 (14) | 0.0272 (10) | 0.0727 (17) | 0.0043 (11) | −0.0187 (14) | −0.0030 (11) |
C6 | 0.094 (2) | 0.0653 (18) | 0.0583 (18) | 0.0079 (19) | −0.009 (2) | −0.0108 (14) |
C19 | 0.0629 (17) | 0.0385 (12) | 0.0722 (18) | −0.0026 (13) | −0.0117 (16) | 0.0103 (12) |
C8 | 0.0531 (14) | 0.0473 (14) | 0.0627 (15) | −0.0033 (13) | −0.0004 (13) | −0.0059 (12) |
C17 | 0.105 (3) | 0.0532 (16) | 0.086 (2) | −0.0084 (19) | −0.028 (2) | 0.0283 (15) |
C5 | 0.074 (2) | 0.0477 (15) | 0.073 (2) | 0.0087 (15) | −0.0260 (18) | −0.0139 (14) |
C18 | 0.069 (2) | 0.117 (3) | 0.098 (3) | −0.043 (2) | −0.011 (2) | −0.013 (2) |
O3—C15 | 1.375 (3) | C7—H7 | 0.93 |
O3—C19 | 1.421 (3) | C3—C4 | 1.336 (5) |
O2—C14 | 1.375 (3) | C3—C2 | 1.409 (4) |
O2—C18 | 1.393 (4) | C3—H3 | 0.93 |
C15—C14 | 1.382 (3) | C2—H2 | 0.93 |
C15—C16 | 1.386 (3) | C4—C10 | 1.411 (4) |
C14—C13 | 1.396 (3) | C4—H4 | 0.93 |
O1—C13 | 1.361 (3) | C10—C5 | 1.404 (4) |
O1—C17 | 1.427 (3) | C6—C5 | 1.345 (5) |
C9—C1 | 1.418 (4) | C6—H6 | 0.93 |
C9—C8 | 1.419 (4) | C19—H19A | 0.96 |
C9—C10 | 1.425 (3) | C19—H19B | 0.96 |
C13—C12 | 1.376 (3) | C19—H19C | 0.96 |
C11—C12 | 1.379 (3) | C8—H8 | 0.93 |
C11—C16 | 1.401 (3) | C17—H17A | 0.96 |
C11—C1 | 1.488 (3) | C17—H17B | 0.96 |
C16—H16 | 0.93 | C17—H17C | 0.96 |
C12—H12 | 0.93 | C5—H5 | 0.93 |
C1—C2 | 1.366 (4) | C18—H18A | 0.96 |
C7—C8 | 1.369 (4) | C18—H18B | 0.96 |
C7—C6 | 1.402 (5) | C18—H18C | 0.96 |
C15—O3—C19 | 117.30 (19) | C3—C2—H2 | 119.2 |
C14—O2—C18 | 115.9 (2) | C3—C4—C10 | 120.9 (3) |
O3—C15—C14 | 115.5 (2) | C3—C4—H4 | 119.5 |
O3—C15—C16 | 123.6 (2) | C10—C4—H4 | 119.5 |
C14—C15—C16 | 120.89 (19) | C5—C10—C4 | 122.1 (3) |
O2—C14—C15 | 121.3 (2) | C5—C10—C9 | 119.1 (3) |
O2—C14—C13 | 119.2 (2) | C4—C10—C9 | 118.7 (3) |
C15—C14—C13 | 119.2 (2) | C5—C6—C7 | 120.8 (3) |
C13—O1—C17 | 117.1 (2) | C5—C6—H6 | 119.6 |
C1—C9—C8 | 122.5 (2) | C7—C6—H6 | 119.6 |
C1—C9—C10 | 119.5 (2) | O3—C19—H19A | 109.5 |
C8—C9—C10 | 118.0 (2) | O3—C19—H19B | 109.5 |
O1—C13—C12 | 124.7 (2) | H19A—C19—H19B | 109.5 |
O1—C13—C14 | 115.1 (2) | O3—C19—H19C | 109.5 |
C12—C13—C14 | 120.2 (2) | H19A—C19—H19C | 109.5 |
C12—C11—C16 | 119.6 (2) | H19B—C19—H19C | 109.5 |
C12—C11—C1 | 121.6 (2) | C7—C8—C9 | 120.8 (3) |
C16—C11—C1 | 118.7 (2) | C7—C8—H8 | 119.6 |
C15—C16—C11 | 119.4 (2) | C9—C8—H8 | 119.6 |
C15—C16—H16 | 120.3 | O1—C17—H17A | 109.5 |
C11—C16—H16 | 120.3 | O1—C17—H17B | 109.5 |
C13—C12—C11 | 120.7 (2) | H17A—C17—H17B | 109.5 |
C13—C12—H12 | 119.7 | O1—C17—H17C | 109.5 |
C11—C12—H12 | 119.7 | H17A—C17—H17C | 109.5 |
C2—C1—C9 | 118.7 (2) | H17B—C17—H17C | 109.5 |
C2—C1—C11 | 119.5 (2) | C6—C5—C10 | 121.2 (3) |
C9—C1—C11 | 121.8 (2) | C6—C5—H5 | 119.4 |
C8—C7—C6 | 119.9 (3) | C10—C5—H5 | 119.4 |
C8—C7—H7 | 120 | O2—C18—H18A | 109.5 |
C6—C7—H7 | 120 | O2—C18—H18B | 109.5 |
C4—C3—C2 | 120.5 (3) | H18A—C18—H18B | 109.5 |
C4—C3—H3 | 119.8 | O2—C18—H18C | 109.5 |
C2—C3—H3 | 119.8 | H18A—C18—H18C | 109.5 |
C1—C2—C3 | 121.6 (3) | H18B—C18—H18C | 109.5 |
C1—C2—H2 | 119.2 |
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