Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807002693/gk2048sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807002693/gk2048IIsup2.hkl |
CCDC reference: 636642
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.004 Å
- R factor = 0.037
- wR factor = 0.082
- Data-to-parameter ratio = 7.4
checkCIF/PLATON results
No syntax errors found
Alert level A PLAT027_ALERT_3_A _diffrn_reflns_theta_full (too) Low ............ 59.97 Deg.
Alert level B THETM01_ALERT_3_B The value of sine(theta_max)/wavelength is less than 0.575 Calculated sin(theta_max)/wavelength = 0.5615 PLAT023_ALERT_3_B Resolution (too) Low [sin(th)/Lambda < 0.6]..... 59.97 Deg.
Alert level C REFNR01_ALERT_3_C Ratio of reflections to parameters is < 8 for a non-centrosymmetric structure, where ZMAX < 18 sine(theta)/lambda 0.5615 Proportion of unique data used 1.0000 Ratio reflections to parameters 7.3699 PLAT030_ALERT_1_C _diffrn_reflns_number .LE. _reflns_number_total ? PLAT032_ALERT_4_C Std. Uncertainty in Flack Parameter too High ... 0.50 PLAT089_ALERT_3_C Poor Data / Parameter Ratio (Zmax .LT. 18) ..... 7.37 PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given ....... ?
Alert level G REFLT03_ALERT_1_G ALERT: Expected hkl max differ from CIF values From the CIF: _diffrn_reflns_theta_max 59.97 From the CIF: _reflns_number_total 1614 From the CIF: _diffrn_reflns_limit_ max hkl 7. 10. 29. From the CIF: _diffrn_reflns_limit_ min hkl 0. 0. 0. TEST1: Expected hkl limits for theta max Calculated maximum hkl 7. 10. 31. Calculated minimum hkl -7. -10. -31. 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 59.97 From the CIF: _reflns_number_total 1614 Count of symmetry unique reflns 1630 Completeness (_total/calc) 99.02% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 0 Fraction of Friedel pairs measured 0.000 Are heavy atom types Z>Si present no PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature 293 K PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature . 293 K PLAT791_ALERT_1_G Confirm the Absolute Configuration of C4 = . R PLAT791_ALERT_1_G Confirm the Absolute Configuration of C5 = . S PLAT791_ALERT_1_G Confirm the Absolute Configuration of C8 = . S PLAT791_ALERT_1_G Confirm the Absolute Configuration of C9 = . R PLAT791_ALERT_1_G Confirm the Absolute Configuration of C10 = . S PLAT791_ALERT_1_G Confirm the Absolute Configuration of C13 = . R PLAT791_ALERT_1_G Confirm the Absolute Configuration of C16 = . R
1 ALERT level A = In general: serious problem 2 ALERT level B = Potentially serious problem 5 ALERT level C = Check and explain 11 ALERT level G = General alerts; check 11 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 5 ALERT type 3 Indicator that the structure quality may be low 3 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
checkCIF publication errors
Alert level A PUBL024_ALERT_1_A The number of authors is greater than 5. Please specify the role of each of the co-authors for your paper.
Author Response: This work is part of a wide international collaborative project which involves synthesis, sample preparations, activities tests, diffraction data collection and data analysis. Students also participate in the project. |
1 ALERT level A = Data missing that is essential or data in wrong format 0 ALERT level G = General alerts. Data that may be required is missing
Data collection: CRYSOM (Martinez-Ripoll & Cano, 1996); cell refinement: CRYSOM; data reduction: X-RAY80 (Stewart et al., 1990); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXL/PC (Sheldrick, 1990); software used to prepare material for publication: SHELXL97.
C21H32O3 | Dx = 1.191 Mg m−3 |
Mr = 332.47 | Cu Kα radiation, λ = 1.54180 Å |
Orthorhombic, P212121 | Cell parameters from 20 reflections |
a = 6.7100 (13) Å | θ = 5.0–10.2° |
b = 9.7380 (19) Å | µ = 0.61 mm−1 |
c = 28.383 (6) Å | T = 293 K |
V = 1854.6 (6) Å3 | Prismatic, colourless |
Z = 4 | 0.2 × 0.2 × 0.2 mm |
F(000) = 728 |
Seifert XRD 3003 SC diffractometer | Rint = 0.000 |
Radiation source: fine-focus sealed tube | θmax = 60.0°, θmin = 3.1° |
Graphite monochromator | h = 0→7 |
ω/2θ scans | k = 0→10 |
1614 measured reflections | l = 0→29 |
1614 independent reflections | 2 standard reflections every 700 reflections |
1274 reflections with I > 2σ(I) | intensity decay: 1% |
Refinement on F2 | Hydrogen site location: inferred from neighbouring sites |
Least-squares matrix: full | H-atom parameters constrained |
R[F2 > 2σ(F2)] = 0.037 | w = 1/[σ2(Fo2) + (0.0423P)2] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.082 | (Δ/σ)max < 0.001 |
S = 1.06 | Δρmax = 0.16 e Å−3 |
1614 reflections | Δρmin = −0.14 e Å−3 |
219 parameters | Extinction correction: SHELXL97 (Sheldrick, 1997), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
0 restraints | Extinction coefficient: 0.0065 (5) |
Primary atom site location: structure-invariant direct methods | Absolute structure: Flack (1983), with no Friedel pairs? |
Secondary atom site location: difference Fourier map | Absolute structure parameter: 0.2 (5) |
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 | ||
O1 | 0.1829 (4) | 0.4715 (3) | 0.26632 (8) | 0.0672 (8) | |
O2 | 0.2572 (3) | 0.6880 (2) | 0.24895 (7) | 0.0534 (6) | |
O3 | 0.2472 (4) | 1.2470 (2) | 0.47775 (7) | 0.0575 (7) | |
C1 | 0.3118 (6) | 0.5504 (3) | 0.40708 (11) | 0.0533 (10) | |
H1A | 0.4358 | 0.5529 | 0.4246 | 0.064* | |
H1B | 0.2046 | 0.5364 | 0.4295 | 0.064* | |
C2 | 0.3173 (7) | 0.4285 (3) | 0.37330 (13) | 0.0696 (13) | |
H2A | 0.3469 | 0.3454 | 0.3908 | 0.084* | |
H2B | 0.1874 | 0.4174 | 0.3588 | 0.084* | |
C3 | 0.4726 (7) | 0.4482 (3) | 0.33535 (12) | 0.0648 (11) | |
H3A | 0.4633 | 0.3724 | 0.3133 | 0.078* | |
H3B | 0.6035 | 0.4445 | 0.3498 | 0.078* | |
C4 | 0.4546 (5) | 0.5819 (3) | 0.30808 (10) | 0.0441 (8) | |
C5 | 0.4436 (4) | 0.7035 (3) | 0.34378 (10) | 0.0342 (7) | |
H5A | 0.5693 | 0.6969 | 0.3612 | 0.041* | |
C6 | 0.4487 (5) | 0.8469 (3) | 0.32289 (10) | 0.0404 (8) | |
H6A | 0.3190 | 0.8694 | 0.3099 | 0.048* | |
H6B | 0.5456 | 0.8504 | 0.2976 | 0.048* | |
C7 | 0.5039 (5) | 0.9512 (3) | 0.36078 (10) | 0.0423 (8) | |
H7A | 0.6356 | 0.9299 | 0.3728 | 0.051* | |
H7B | 0.5090 | 1.0420 | 0.3468 | 0.051* | |
C8 | 0.3563 (4) | 0.9523 (3) | 0.40153 (9) | 0.0300 (7) | |
C9 | 0.3205 (4) | 0.8048 (3) | 0.42022 (9) | 0.0301 (7) | |
H9A | 0.4478 | 0.7789 | 0.4346 | 0.036* | |
C10 | 0.2816 (5) | 0.6904 (3) | 0.38268 (9) | 0.0332 (7) | |
C11 | 0.1727 (5) | 0.8090 (3) | 0.46211 (10) | 0.0402 (8) | |
H11A | 0.1180 | 0.7176 | 0.4664 | 0.048* | |
H11B | 0.2468 | 0.8316 | 0.4904 | 0.048* | |
C12 | −0.0001 (5) | 0.9099 (3) | 0.45756 (11) | 0.0459 (8) | |
H12A | −0.0996 | 0.8719 | 0.4365 | 0.055* | |
H12B | −0.0616 | 0.9227 | 0.4882 | 0.055* | |
C13 | 0.0686 (5) | 1.0487 (3) | 0.43871 (10) | 0.0427 (8) | |
H13A | −0.0403 | 1.1158 | 0.4379 | 0.051* | |
C14 | 0.1592 (5) | 1.0252 (3) | 0.38958 (10) | 0.0384 (8) | |
H14A | 0.1827 | 1.1114 | 0.3734 | 0.046* | |
H14B | 0.0740 | 0.9676 | 0.3703 | 0.046* | |
C15 | 0.4320 (5) | 1.0451 (3) | 0.44235 (10) | 0.0409 (8) | |
H15A | 0.5109 | 0.9921 | 0.4645 | 0.049* | |
H15B | 0.5133 | 1.1194 | 0.4302 | 0.049* | |
C16 | 0.2456 (5) | 1.1012 (3) | 0.46614 (11) | 0.0407 (8) | |
C17 | 0.2353 (6) | 1.1458 (3) | 0.51503 (11) | 0.0528 (9) | |
H17A | 0.1090 | 1.1357 | 0.5313 | 0.063* | |
H17B | 0.3522 | 1.1322 | 0.5346 | 0.063* | |
C18 | 0.6431 (5) | 0.5976 (4) | 0.27696 (12) | 0.0651 (11) | |
H18A | 0.6352 | 0.6818 | 0.2595 | 0.098* | |
H18B | 0.6515 | 0.5216 | 0.2555 | 0.098* | |
H18C | 0.7595 | 0.5990 | 0.2966 | 0.098* | |
C19 | 0.2806 (5) | 0.5727 (3) | 0.27360 (10) | 0.0420 (8) | |
C20 | 0.0700 (4) | 0.6941 (3) | 0.36222 (10) | 0.0429 (8) | |
H20A | 0.0554 | 0.6222 | 0.3393 | 0.064* | |
H20B | 0.0473 | 0.7814 | 0.3474 | 0.064* | |
H20C | −0.0250 | 0.6811 | 0.3871 | 0.064* | |
C21 | 0.1063 (5) | 0.6890 (4) | 0.21251 (11) | 0.0632 (10) | |
H21A | 0.1038 | 0.7775 | 0.1976 | 0.095* | |
H21B | −0.0216 | 0.6704 | 0.2263 | 0.095* | |
H21C | 0.1365 | 0.6199 | 0.1895 | 0.095* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0743 (18) | 0.0564 (14) | 0.0708 (16) | −0.0180 (15) | −0.0179 (14) | −0.0106 (14) |
O2 | 0.0533 (13) | 0.0564 (14) | 0.0506 (13) | −0.0068 (14) | −0.0154 (13) | −0.0027 (12) |
O3 | 0.0744 (16) | 0.0295 (10) | 0.0687 (14) | −0.0012 (13) | 0.0065 (15) | −0.0100 (12) |
C1 | 0.088 (3) | 0.0263 (16) | 0.0457 (18) | −0.0034 (19) | 0.0003 (19) | 0.0042 (15) |
C2 | 0.122 (4) | 0.0259 (18) | 0.060 (2) | 0.002 (2) | −0.013 (3) | 0.0026 (17) |
C3 | 0.088 (3) | 0.043 (2) | 0.064 (2) | 0.021 (2) | −0.020 (2) | −0.017 (2) |
C4 | 0.0408 (19) | 0.046 (2) | 0.0458 (19) | 0.0085 (18) | −0.0068 (16) | −0.0131 (17) |
C5 | 0.0331 (17) | 0.0349 (17) | 0.0345 (16) | 0.0006 (15) | −0.0073 (15) | −0.0093 (14) |
C6 | 0.0451 (19) | 0.0418 (17) | 0.0341 (16) | −0.0071 (16) | 0.0099 (16) | −0.0027 (15) |
C7 | 0.046 (2) | 0.0375 (17) | 0.0438 (18) | −0.0115 (17) | 0.0083 (16) | 0.0005 (16) |
C8 | 0.0328 (16) | 0.0254 (15) | 0.0319 (16) | −0.0004 (15) | −0.0017 (13) | −0.0024 (13) |
C9 | 0.0330 (16) | 0.0297 (15) | 0.0275 (15) | 0.0001 (14) | −0.0028 (13) | 0.0004 (13) |
C10 | 0.0438 (19) | 0.0266 (15) | 0.0293 (15) | −0.0033 (16) | −0.0043 (15) | 0.0014 (12) |
C11 | 0.0500 (19) | 0.0383 (17) | 0.0323 (16) | −0.0056 (17) | 0.0016 (15) | 0.0007 (15) |
C12 | 0.0374 (18) | 0.056 (2) | 0.0444 (18) | −0.0028 (17) | 0.0051 (15) | −0.0079 (17) |
C13 | 0.0391 (19) | 0.0374 (18) | 0.0516 (19) | 0.0102 (17) | −0.0021 (16) | −0.0078 (17) |
C14 | 0.0444 (18) | 0.0276 (16) | 0.0433 (17) | 0.0011 (16) | −0.0070 (16) | 0.0000 (14) |
C15 | 0.0404 (19) | 0.0360 (17) | 0.0463 (18) | −0.0028 (17) | −0.0007 (16) | −0.0053 (17) |
C16 | 0.0464 (18) | 0.0263 (15) | 0.0495 (18) | 0.0024 (16) | 0.0010 (18) | −0.0105 (14) |
C17 | 0.066 (2) | 0.0417 (18) | 0.051 (2) | −0.001 (2) | 0.000 (2) | −0.0092 (16) |
C18 | 0.039 (2) | 0.089 (3) | 0.067 (2) | 0.009 (2) | −0.0013 (19) | −0.040 (2) |
C19 | 0.042 (2) | 0.045 (2) | 0.0390 (18) | 0.0002 (18) | 0.0024 (16) | −0.0106 (16) |
C20 | 0.0392 (18) | 0.0458 (19) | 0.0437 (18) | −0.0118 (17) | 0.0034 (16) | −0.0090 (16) |
C21 | 0.058 (2) | 0.085 (3) | 0.047 (2) | −0.001 (2) | −0.0171 (19) | −0.003 (2) |
O1—C19 | 1.201 (4) | C9—C11 | 1.549 (4) |
O2—C19 | 1.332 (4) | C9—C10 | 1.564 (4) |
O2—C21 | 1.448 (3) | C9—H9A | 0.9800 |
O3—C17 | 1.448 (3) | C10—C20 | 1.534 (4) |
O3—C16 | 1.458 (3) | C11—C12 | 1.525 (4) |
C1—C2 | 1.527 (4) | C11—H11A | 0.9700 |
C1—C10 | 1.543 (4) | C11—H11B | 0.9700 |
C1—H1A | 0.9700 | C12—C13 | 1.525 (4) |
C1—H1B | 0.9700 | C12—H12A | 0.9700 |
C2—C3 | 1.511 (5) | C12—H12B | 0.9700 |
C2—H2A | 0.9700 | C13—C16 | 1.509 (4) |
C2—H2B | 0.9700 | C13—C14 | 1.538 (4) |
C3—C4 | 1.519 (4) | C13—H13A | 0.9800 |
C3—H3A | 0.9700 | C14—H14A | 0.9700 |
C3—H3B | 0.9700 | C14—H14B | 0.9700 |
C4—C19 | 1.526 (4) | C15—C16 | 1.523 (4) |
C4—C18 | 1.550 (4) | C15—H15A | 0.9700 |
C4—C5 | 1.560 (4) | C15—H15B | 0.9700 |
C5—C6 | 1.518 (4) | C16—C17 | 1.456 (4) |
C5—C10 | 1.555 (4) | C17—H17A | 0.9700 |
C5—H5A | 0.9800 | C17—H17B | 0.9700 |
C6—C7 | 1.525 (4) | C18—H18A | 0.9600 |
C6—H6A | 0.9700 | C18—H18B | 0.9600 |
C6—H6B | 0.9700 | C18—H18C | 0.9600 |
C7—C8 | 1.523 (4) | C20—H20A | 0.9600 |
C7—H7A | 0.9700 | C20—H20B | 0.9600 |
C7—H7B | 0.9700 | C20—H20C | 0.9600 |
C8—C14 | 1.538 (4) | C21—H21A | 0.9600 |
C8—C9 | 1.550 (4) | C21—H21B | 0.9600 |
C8—C15 | 1.555 (4) | C21—H21C | 0.9600 |
C19—O2—C21 | 117.6 (3) | C12—C11—H11A | 108.3 |
C17—O3—C16 | 60.12 (18) | C9—C11—H11A | 108.3 |
C2—C1—C10 | 114.1 (2) | C12—C11—H11B | 108.3 |
C2—C1—H1A | 108.7 | C9—C11—H11B | 108.3 |
C10—C1—H1A | 108.7 | H11A—C11—H11B | 107.4 |
C2—C1—H1B | 108.7 | C13—C12—C11 | 111.8 (3) |
C10—C1—H1B | 108.7 | C13—C12—H12A | 109.3 |
H1A—C1—H1B | 107.6 | C11—C12—H12A | 109.3 |
C3—C2—C1 | 111.4 (3) | C13—C12—H12B | 109.3 |
C3—C2—H2A | 109.3 | C11—C12—H12B | 109.3 |
C1—C2—H2A | 109.3 | H12A—C12—H12B | 107.9 |
C3—C2—H2B | 109.3 | C16—C13—C12 | 110.9 (3) |
C1—C2—H2B | 109.3 | C16—C13—C14 | 102.0 (2) |
H2A—C2—H2B | 108.0 | C12—C13—C14 | 107.8 (3) |
C2—C3—C4 | 114.7 (3) | C16—C13—H13A | 111.9 |
C2—C3—H3A | 108.6 | C12—C13—H13A | 111.9 |
C4—C3—H3A | 108.6 | C14—C13—H13A | 111.9 |
C2—C3—H3B | 108.6 | C13—C14—C8 | 102.0 (2) |
C4—C3—H3B | 108.6 | C13—C14—H14A | 111.4 |
H3A—C3—H3B | 107.6 | C8—C14—H14A | 111.4 |
C3—C4—C19 | 109.7 (3) | C13—C14—H14B | 111.4 |
C3—C4—C18 | 108.1 (3) | C8—C14—H14B | 111.4 |
C19—C4—C18 | 105.3 (2) | H14A—C14—H14B | 109.2 |
C3—C4—C5 | 108.8 (2) | C16—C15—C8 | 105.7 (2) |
C19—C4—C5 | 115.1 (3) | C16—C15—H15A | 110.6 |
C18—C4—C5 | 109.5 (3) | C8—C15—H15A | 110.6 |
C6—C5—C10 | 111.6 (2) | C16—C15—H15B | 110.6 |
C6—C5—C4 | 116.4 (2) | C8—C15—H15B | 110.6 |
C10—C5—C4 | 115.6 (2) | H15A—C15—H15B | 108.7 |
C6—C5—H5A | 103.8 | C17—C16—O3 | 59.63 (17) |
C10—C5—H5A | 103.8 | C17—C16—C13 | 123.7 (3) |
C4—C5—H5A | 103.8 | O3—C16—C13 | 116.9 (3) |
C5—C6—C7 | 110.1 (2) | C17—C16—C15 | 124.7 (3) |
C5—C6—H6A | 109.6 | O3—C16—C15 | 116.4 (3) |
C7—C6—H6A | 109.6 | C13—C16—C15 | 107.2 (2) |
C5—C6—H6B | 109.6 | O3—C17—C16 | 60.26 (18) |
C7—C6—H6B | 109.6 | O3—C17—H17A | 117.7 |
H6A—C6—H6B | 108.2 | C16—C17—H17A | 117.7 |
C8—C7—C6 | 112.5 (2) | O3—C17—H17B | 117.7 |
C8—C7—H7A | 109.1 | C16—C17—H17B | 117.7 |
C6—C7—H7A | 109.1 | H17A—C17—H17B | 114.9 |
C8—C7—H7B | 109.1 | C4—C18—H18A | 109.5 |
C6—C7—H7B | 109.1 | C4—C18—H18B | 109.5 |
H7A—C7—H7B | 107.8 | H18A—C18—H18B | 109.5 |
C7—C8—C14 | 113.3 (2) | C4—C18—H18C | 109.5 |
C7—C8—C9 | 110.7 (2) | H18A—C18—H18C | 109.5 |
C14—C8—C9 | 111.7 (2) | H18B—C18—H18C | 109.5 |
C7—C8—C15 | 110.9 (2) | O1—C19—O2 | 122.4 (3) |
C14—C8—C15 | 100.2 (2) | O1—C19—C4 | 125.2 (3) |
C9—C8—C15 | 109.5 (2) | O2—C19—C4 | 112.2 (3) |
C11—C9—C8 | 109.7 (2) | C10—C20—H20A | 109.5 |
C11—C9—C10 | 115.8 (2) | C10—C20—H20B | 109.5 |
C8—C9—C10 | 116.9 (2) | H20A—C20—H20B | 109.5 |
C11—C9—H9A | 104.2 | C10—C20—H20C | 109.5 |
C8—C9—H9A | 104.2 | H20A—C20—H20C | 109.5 |
C10—C9—H9A | 104.2 | H20B—C20—H20C | 109.5 |
C20—C10—C1 | 108.2 (3) | O2—C21—H21A | 109.5 |
C20—C10—C5 | 112.1 (2) | O2—C21—H21B | 109.5 |
C1—C10—C5 | 107.4 (3) | H21A—C21—H21B | 109.5 |
C20—C10—C9 | 113.3 (2) | O2—C21—H21C | 109.5 |
C1—C10—C9 | 107.6 (2) | H21A—C21—H21C | 109.5 |
C5—C10—C9 | 108.0 (2) | H21B—C21—H21C | 109.5 |
C12—C11—C9 | 116.0 (2) |
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