Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270101001433/av1062sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S0108270101001433/av1062Isup2.hkl |
CCDC reference: 163948
Data collection: XSCANS (Siemens, 1996a); cell refinement: XSCANS; data reduction: SHELXTL (Siemens, 1996b); program(s) used to solve structure: SIR97 (Altomare, 1994); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: XPW in SHELXTL; software used to prepare material for publication: locally modified PARST97 (Nardelli, 1995) and SHELXL97.
C17H10O3 | F(000) = 1088 |
Mr = 262.25 | Dx = 1.413 Mg m−3 |
Orthorhombic, Pbca | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ac 2ab | Cell parameters from 48 reflections |
a = 13.4239 (11) Å | θ = 3.0–12.4° |
b = 7.2198 (5) Å | µ = 0.10 mm−1 |
c = 25.441 (3) Å | T = 298 K |
V = 2465.7 (4) Å3 | Irregular, colourless |
Z = 8 | 0.39 × 0.25 × 0.18 mm |
Siemens P4 diffractometer | 1189 reflections with I > 2σ(I) |
Radiation source: sealed tube | Rint = 0.029 |
Graphite monochromator | θmax = 25.0°, θmin = 2.2° |
ω scans | h = −1→15 |
Absorption correction: ψ scan (Kopfmann & Huber, 1968) | k = −1→8 |
Tmin = 0.241, Tmax = 0.272 | l = −30→1 |
2877 measured reflections | 3 standard reflections every 197 reflections |
2170 independent reflections | intensity decay: 12% |
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)] = 0.052 | H-atom parameters constrained |
wR(F2) = 0.123 | w = 1/[σ2(Fo2) + (0.053P)2] where P = (Fo2 + 2Fc2)/3 |
S = 0.98 | (Δ/σ)max < 0.001 |
2170 reflections | Δρmax = 0.18 e Å−3 |
182 parameters | Δρmin = −0.15 e Å−3 |
0 restraints | Extinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.0057 (7) |
Experimental. Due to the irregular shape, the crystal sample dimension might be considered approsimate The reflection profiles have not the usual Gaussian shape but they show an evident broading that might be related to mosaic structure of the packing. Reflection intensities were evaluated by profile fitting of a 96-steps peak scan among 2θ shells (Diamond, 1969). The observed decay of the diffraction data might be due to the deterioration of the crystal packing caused by the increase of its mosaic structure. An absorption correction was applied by fitting a pseudo-ellipsoid to the azimuthal scan data (0–360° range by a 10° step) of 12 high χ reflections (Kopfmann & Huber, 1968). Whereas the final difference Fourier maps showed several H-atom positions. |
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. All calculations were performed on a µ-VAX 3400 and on a DEC-alpha 3000/400. An empirical extinction parameter was included in the final refinement cycles. |
x | y | z | Uiso*/Ueq | ||
O1 | 0.41972 (12) | 0.2889 (2) | 0.03889 (7) | 0.0585 (5) | |
O2 | 0.42723 (14) | 0.2967 (2) | 0.12534 (7) | 0.0713 (6) | |
O3 | 0.33758 (12) | −0.2514 (2) | 0.04435 (7) | 0.0582 (6) | |
C1 | 0.36380 (17) | −0.0710 (3) | 0.03828 (10) | 0.0497 (7) | |
C2 | 0.36886 (17) | 0.0195 (4) | −0.01134 (10) | 0.0493 (7) | |
C3 | 0.34655 (19) | −0.0565 (4) | −0.06025 (11) | 0.0600 (7) | |
H3 | 0.3255 | −0.1790 | −0.0627 | 0.075* | |
C4 | 0.3555 (2) | 0.0489 (5) | −0.10464 (11) | 0.0682 (9) | |
H4 | 0.3399 | −0.0019 | −0.1372 | 0.075* | |
C5 | 0.3879 (2) | 0.2308 (5) | −0.10142 (11) | 0.0682 (9) | |
H5 | 0.3952 | 0.3005 | −0.1319 | 0.075* | |
C6 | 0.40919 (19) | 0.3091 (4) | −0.05337 (11) | 0.0631 (8) | |
H6 | 0.4302 | 0.4316 | −0.0511 | 0.075* | |
C7 | 0.39899 (18) | 0.2031 (4) | −0.00858 (10) | 0.0520 (7) | |
C8 | 0.41059 (19) | 0.2014 (4) | 0.08789 (11) | 0.0534 (7) | |
C9 | 0.38223 (17) | 0.0095 (3) | 0.08548 (9) | 0.0453 (6) | |
C10 | 0.36474 (17) | −0.1291 (3) | 0.12526 (10) | 0.0481 (7) | |
C11 | 0.33999 (18) | −0.2824 (4) | 0.09796 (11) | 0.0572 (7) | |
H11 | 0.3261 | −0.3962 | 0.1134 | 0.075* | |
C12 | 0.36939 (19) | −0.1200 (3) | 0.18342 (11) | 0.0515 (7) | |
C13 | 0.2975 (2) | −0.2103 (4) | 0.21274 (11) | 0.0651 (8) | |
H13 | 0.2447 | −0.2684 | 0.1958 | 0.075* | |
C14 | 0.3032 (2) | −0.2150 (4) | 0.26671 (12) | 0.0759 (9) | |
H14 | 0.2548 | −0.2773 | 0.2859 | 0.075* | |
C15 | 0.3800 (2) | −0.1283 (4) | 0.29221 (12) | 0.0726 (9) | |
H15 | 0.3839 | −0.1326 | 0.3287 | 0.075* | |
C16 | 0.4511 (2) | −0.0349 (4) | 0.26399 (10) | 0.0689 (8) | |
H16 | 0.5030 | 0.0249 | 0.2813 | 0.075* | |
C17 | 0.4454 (2) | −0.0301 (4) | 0.20961 (10) | 0.0603 (8) | |
H17 | 0.4933 | 0.0344 | 0.1906 | 0.075* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0695 (13) | 0.0435 (10) | 0.0625 (12) | −0.0040 (10) | −0.0072 (10) | 0.0034 (10) |
O2 | 0.1025 (16) | 0.0441 (11) | 0.0674 (12) | −0.0056 (11) | −0.0169 (11) | −0.0090 (10) |
O3 | 0.0594 (12) | 0.0458 (11) | 0.0695 (13) | −0.0088 (9) | −0.0044 (10) | −0.0061 (9) |
C1 | 0.0393 (14) | 0.0429 (15) | 0.0668 (18) | 0.0001 (13) | −0.0010 (13) | −0.0041 (14) |
C2 | 0.0369 (14) | 0.0504 (17) | 0.0605 (17) | 0.0004 (14) | −0.0032 (13) | −0.0062 (15) |
C3 | 0.0513 (17) | 0.0615 (17) | 0.0671 (18) | −0.0002 (15) | −0.0039 (14) | −0.0086 (16) |
C4 | 0.0612 (19) | 0.084 (2) | 0.060 (2) | 0.0061 (18) | −0.0046 (15) | −0.0052 (18) |
C5 | 0.064 (2) | 0.080 (2) | 0.0602 (19) | 0.0113 (19) | 0.0011 (16) | 0.0107 (17) |
C6 | 0.0591 (18) | 0.0563 (17) | 0.074 (2) | 0.0059 (15) | −0.0035 (15) | 0.0087 (17) |
C7 | 0.0429 (15) | 0.0507 (17) | 0.0622 (17) | 0.0061 (15) | −0.0050 (13) | 0.0000 (15) |
C8 | 0.0518 (16) | 0.0419 (15) | 0.0666 (18) | 0.0028 (14) | −0.0091 (14) | 0.0016 (15) |
C9 | 0.0432 (14) | 0.0358 (14) | 0.0569 (16) | 0.0014 (13) | −0.0035 (12) | −0.0025 (13) |
C10 | 0.0406 (14) | 0.0409 (15) | 0.0629 (17) | 0.0011 (13) | −0.0013 (13) | −0.0026 (14) |
C11 | 0.0536 (17) | 0.0479 (16) | 0.070 (2) | −0.0069 (14) | −0.0028 (14) | 0.0076 (16) |
C12 | 0.0500 (16) | 0.0411 (15) | 0.0634 (17) | 0.0023 (14) | −0.0020 (14) | 0.0045 (13) |
C13 | 0.0668 (19) | 0.0557 (18) | 0.073 (2) | −0.0092 (16) | −0.0018 (16) | 0.0066 (17) |
C14 | 0.087 (2) | 0.065 (2) | 0.076 (2) | −0.0150 (19) | 0.0092 (19) | 0.0129 (19) |
C15 | 0.102 (3) | 0.0542 (19) | 0.0618 (19) | 0.0040 (19) | 0.0022 (19) | 0.0020 (16) |
C16 | 0.074 (2) | 0.063 (2) | 0.070 (2) | −0.0028 (18) | −0.0106 (17) | −0.0048 (17) |
C17 | 0.0579 (18) | 0.0555 (17) | 0.0675 (18) | −0.0063 (16) | −0.0026 (15) | −0.0007 (16) |
O1—C7 | 1.385 (3) | C6—C7 | 1.380 (3) |
O1—C8 | 1.403 (3) | C8—C9 | 1.438 (3) |
O2—C8 | 1.196 (3) | C9—C10 | 1.442 (3) |
O3—C1 | 1.358 (3) | C10—C11 | 1.348 (3) |
O3—C11 | 1.383 (3) | C10—C12 | 1.482 (3) |
C1—C9 | 1.357 (3) | C12—C17 | 1.381 (3) |
C1—C2 | 1.423 (3) | C12—C13 | 1.382 (3) |
C2—C7 | 1.388 (3) | C13—C14 | 1.376 (3) |
C2—C3 | 1.393 (3) | C14—C15 | 1.369 (4) |
C3—C4 | 1.367 (4) | C15—C16 | 1.372 (3) |
C4—C5 | 1.386 (4) | C16—C17 | 1.386 (3) |
C5—C6 | 1.377 (3) | ||
C7—O1—C8 | 123.8 (2) | O1—C8—C9 | 114.8 (2) |
C1—O3—C11 | 105.14 (19) | C1—C9—C8 | 119.9 (2) |
C9—C1—O3 | 111.0 (2) | C1—C9—C10 | 107.1 (2) |
C9—C1—C2 | 125.4 (2) | C8—C9—C10 | 133.0 (2) |
O3—C1—C2 | 123.6 (2) | C11—C10—C9 | 104.4 (2) |
C7—C2—C3 | 119.0 (3) | C11—C10—C12 | 124.1 (2) |
C7—C2—C1 | 114.0 (2) | C9—C10—C12 | 131.5 (2) |
C3—C2—C1 | 127.0 (3) | C10—C11—O3 | 112.4 (2) |
C4—C3—C2 | 120.0 (3) | C17—C12—C13 | 118.5 (3) |
C3—C4—C5 | 120.4 (3) | C17—C12—C10 | 122.2 (2) |
C6—C5—C4 | 120.4 (3) | C13—C12—C10 | 119.2 (2) |
C5—C6—C7 | 119.0 (3) | C14—C13—C12 | 120.8 (3) |
C6—C7—O1 | 116.9 (3) | C15—C14—C13 | 120.2 (3) |
C6—C7—C2 | 121.1 (3) | C14—C15—C16 | 120.0 (3) |
O1—C7—C2 | 122.0 (2) | C15—C16—C17 | 119.7 (3) |
O2—C8—O1 | 115.6 (2) | C12—C17—C16 | 120.7 (3) |
O2—C8—C9 | 129.6 (3) | ||
C11—O3—C1—C9 | 0.1 (3) | C2—C1—C9—C10 | 177.7 (2) |
C11—O3—C1—C2 | −178.8 (2) | O2—C8—C9—C1 | 177.9 (3) |
C9—C1—C2—C7 | 2.4 (4) | O1—C8—C9—C1 | −1.9 (3) |
O3—C1—C2—C7 | −178.9 (2) | O2—C8—C9—C10 | 0.0 (5) |
C9—C1—C2—C3 | −177.2 (2) | O1—C8—C9—C10 | −179.9 (2) |
O3—C1—C2—C3 | 1.5 (4) | C1—C9—C10—C11 | 1.7 (3) |
C7—C2—C3—C4 | 0.7 (4) | C8—C9—C10—C11 | 179.8 (3) |
C1—C2—C3—C4 | −179.7 (2) | C1—C9—C10—C12 | −177.6 (2) |
C2—C3—C4—C5 | 0.7 (4) | C8—C9—C10—C12 | 0.6 (5) |
C3—C4—C5—C6 | −1.5 (4) | C9—C10—C11—O3 | −1.7 (3) |
C4—C5—C6—C7 | 0.7 (4) | C12—C10—C11—O3 | 177.6 (2) |
C5—C6—C7—O1 | −179.0 (2) | C1—O3—C11—C10 | 1.1 (3) |
C5—C6—C7—C2 | 0.7 (4) | C11—C10—C12—C17 | 137.7 (3) |
C8—O1—C7—C6 | 178.4 (2) | C9—C10—C12—C17 | −43.2 (4) |
C8—O1—C7—C2 | −1.3 (4) | C11—C10—C12—C13 | −39.8 (4) |
C3—C2—C7—C6 | −1.5 (4) | C9—C10—C12—C13 | 139.3 (3) |
C1—C2—C7—C6 | 178.9 (2) | C17—C12—C13—C14 | −1.9 (4) |
C3—C2—C7—O1 | 178.2 (2) | C10—C12—C13—C14 | 175.7 (2) |
C1—C2—C7—O1 | −1.4 (3) | C12—C13—C14—C15 | 0.7 (5) |
C7—O1—C8—O2 | −177.0 (2) | C13—C14—C15—C16 | 0.5 (5) |
C7—O1—C8—C9 | 2.9 (3) | C14—C15—C16—C17 | −0.5 (4) |
O3—C1—C9—C8 | −179.6 (2) | C13—C12—C17—C16 | 1.9 (4) |
C2—C1—C9—C8 | −0.7 (4) | C10—C12—C17—C16 | −175.6 (2) |
O3—C1—C9—C10 | −1.1 (3) | C15—C16—C17—C12 | −0.7 (4) |